Patent Description:
Luminescent compounds are widely used in industrial and research applications as, for example, dyes, probes, sensors, and in electronic devices. These molecules emit light under external energy excitation from sources such as light and/or electrical current.

In photoluminescence, under light irradiation a luminescent compound will absorb light of a specific wavelength and re-emit light of a different wavelength. The type of photoemission observed depends on the molecular structure of the compound.

The difference between the maximum excitation wavelength and the emission wavelength of a luminescent compound is known as the Stokes shift. For use as dyes, probes and/or sensors in industrial applications, it is advantageous for luminescent compounds to possess a large Stokes shift, often defined as greater than <NUM>-<NUM> i.e. a comparatively large difference between the excitation wavelength and emission wavelength. This is advantageous because it minimises the reabsorption of light from the emission of the molecule.

A drawback of many fluorescent dyes with large Stokes shifts is their relatively low brightness, this being defined as the product of the molar extinction coefficient and fluorescence quantum yield. Additionally, dyes with large Stokes shifts often suffer from poor photostability (<NPL>).

Organometallic complexes that are luminescent often have a large Stokes shift. However, these contain metal centres, e.g. osmium, ruthenium, iridium, rhenium and so on, which are rare, expensive, the complexes are often difficult to synthesise and often toxic. Luminescent organic molecules are often easier to synthesise, but usually exhibit a Stokes shift of relatively smaller magnitude.

In contrast, in electroluminescence, a luminescent compound will emit light in response to an electric current. One of the main applications for this phenomenon is in electronic devices containing OLEDs (Organic Light Emitting Diodes). The OLED material is a layer of a luminescent organic compound, which is situated between two electrodes, one of which is typically transparent. This technology is used in digital displays in electronic devices such as televisions screens, computer monitors, mobile phones, electroluminescent lighting panels and so on.

It is advantageous for luminescent compounds for use in electroluminescent applications to exhibit high brightness. Brightness is defined as the product of the molar extinction coefficient (E) and fluorescence quantum yield (Φ) divided by <NUM>. Consequently, it is advantageous for luminescent compounds to exhibit a high molar extinction coefficient (E) (defined by the Beer-Lambert law, in which A is absorbance, c is the molar concentration of the luminescent compound, and I is the path length), and also a high quantum yield (Φ) as a measure of efficiency.

It is well known that polycyclic aromatic hydrocarbons exhibit luminescent properties. One such class of compound is triphenylene and its derivatives. For example, triphenylene may be functionalised with alkoxy chains appended to the periphery of the molecule. In addition, these derivatives exhibit discotic liquid crystalline (DLC) behaviour (<NPL>). Discotic liquid crystalline behaviour is characterised in that disc-shaped molecules form stacks or columns in a mesophase, which allows charge transfer through π stacking, enabling the material to be electrically semiconductive in the stacking direction. This DLC behaviour, combined with the luminescent properties, is particularly useful for application in technologies such as electronic devices using OLEDs (Organic Light Emitting Diodes), LEDs (Light Emitting Diodes), and for use in solar cells.

It is also known for luminescent compounds to exhibit photoconductivity, in which compounds exhibit increased electrical conductivity in the presence of light by converting the light energy into current. It is known to utilise compounds with good photoconductivity in devices such as solar cells.

Although many luminescent triphenylene derivatives have been synthesised and characterised (<NPL>, for example), it remains a challenge to provide triphenylene derivatives with the advantageous properties described above, i.e. large Stokes shift, high brightness, high molar extinction coefficient, and high quantum yield. Furthermore, it remains a challenge to provide a range of luminescent compounds that emit wavelengths throughout the visible spectrum. Specifically, blue emitters are a particular challenge to provide (<NPL>).

Furthermore, it remains a challenge to provide luminescent triphenylene derivatives wherein the absorption and the emission energies can be predicted and tuned by design and synthesis to result in specific and desired visible colours (<NPL>).

<CIT> discloses triphenylene derivatives for use as a hole injection layer in an electroluminescence device.

<CIT> discloses organic materials as a fluorescent emitting guests in emitting layers in a light emitting diode.

The invention provides polycyclic aromatic hydrocarbon derivatives according to appended Claims <NUM>-<NUM>.

Also described (but not claimed) are polycyclic aromatic hydrocarbon derivatives represented by the following general formula:
<CHM>
wherein R independently represents an aromatic group and/or an aliphatic group;.

In embodiments, Q may represent C<NUM>H<NUM>. In embodiments, Q is a polycyclic aromatic hydrocarbon, for example, Q may be one of naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene, and/or benzo[c]fluorene. Q may be any isomer of the polycyclic aromatic hydrocarbons described, for example, <NUM>-napthalene, <NUM>-napthalene, <NUM>-anthracene, <NUM>-anthracene. The polycyclic aromatic hydrocarbon group may be substituted with other moieties such as aryl groups, alkyl groups, heteroatoms, and/or other electron withdrawing or electron donating groups.

Q is bonded to other six membered rings, e.g. aromatic six membered rings, and/or substituted aromatic six membered rings. The number of six membered rings bonded to Q is represented by the integer x wherein x is <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> or more.

Q may be an aromatic six-membered ring, and x an integer of <NUM> or above, e.g. <NUM>, <NUM>, <NUM>, <NUM> or above <NUM>.

The described (but not claimed) polycyclic aromatic hydrocarbon, e.g. triphenylene, derivatives may be represented by the following general formula:
<CHM>.

For example, D may be a linear or branched alkyl chain, an aryl group, or a combination thereof.

The described (but not claimed) polycyclic aromatic hydrocarbon, e.g. the triphenylene, derivatives may be represented by the following general formula:
<CHM>.

Y<NUM>, Y<NUM>, and Y<NUM> may comprise a carboxylic acid group, a glycol, an alkoxy, a thioalkoxy, an amino, an acetate, an amide, a thioamide, a thioester, an azo, and/or a silyl group. Additionally or alternatively, Y<NUM>, Y<NUM>, and Y<NUM> may comprise an alkyl group. The alkyl group(s) may be a straight chain, or may comprise a branched chain, and/or may be further functionalised. Additionally or alternatively, Y<NUM>, Y<NUM>, and Y<NUM> may comprise an aryl group. The aryl group(s) may be unsubstituted or may be further functionalised.

One aspect of the invention provides polycyclic aromatic hydrocarbon derivatives, according to Claim <NUM>.

It is also described that the polycyclic aromatic hydrocarbon derivatives may be triphenylene derivatives, represented by the following general formula:
<CHM>.

In embodiments, A may be C<NUM>H<NUM> and/or C<NUM>H<NUM>. In embodiments, A represents a polyethylene glycol (PEG) group (e.g. C<NUM>H<NUM>OC<NUM>H<NUM>OC<NUM>H<NUM>OCH<NUM>.

In embodiments, the triphenylene derivative may not be the compound wherein A is C<NUM>H<NUM>, J is H and R is C<NUM>H<NUM>.

A further aspect of the invention is as set out in Claim <NUM>.

In embodiments, the polycyclic aromatic hydrocarbons are triphenylene derivatives represented by the following general formula:
<CHM>.

A further aspect of the invention provides polycyclic aromatic hydrocarbons as set out in Claim <NUM>.

In non-claimed embodiments, A comprises further functionality, for example, A may further comprise fluorine atoms, chlorine atoms, cyano groups, nitro groups, glycol, alkoxy, thioalkoxy, polyethylene glycol, amino, acetate, carboxylic acid, amide, thioamide, thioester, azo, and/or silyl groups.

In embodiments, J comprises or represents an aryl group, e.g. a phenol group. Additionally or alternatively, J comprises a halogen atom, e.g. fluorine, chlorine, bromine, or iodine.

In embodiments, R, R<NUM>, R<NUM>, or R<NUM> may be an alkyl group, for example, a straight or branched alkyl chain. In embodiments, at least one of R, R<NUM>, R<NUM>, R<NUM> may be a methyl, ethyl, propyl, butyl group.

In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> is an aromatic group, the aromatic group may be one of, or a combination of, an aromatic hydrocarbon group, and/or an aromatic heterocyclic group.

In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> is an aromatic hydrocarbon group, the aromatic hydrocarbon group may comprise one of, or a combination of, a phenyl ring and/or a substituted phenyl ring. There may be one, two, three, four, or five additional substituents on the phenyl ring. The substituents are bonded directly to the phenyl ring, and may be one of, or a combination of, fluorine, chlorine, bromine, iodine, a hydroxyl group, an amine group, a nitro group, an alkoxy group, a carboxylic acid, an amide, a cyano group, a trifluoromethyl, an ester, an alkene an alkyne, an azide, an azo, an isocyanate, a ketone, an aldehyde, an alkyl group consisting of a hydrocarbon chain, or a hydrocarbon ring, an alkyl group consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen, and/or sulphur. The alkyl group may comprise a hydroxyl group, an amine group, a nitro group, an ether group, a carboxylic acid, an amide, a cyano group, trifluoromethyl, an ester, an alkene an alkyne, an azide, an azo, an isocyanate, a ketone, an aldehyde, for example. The substituents may be another aromatic group, for example, R may comprise a phenyl substituted with a further phenyl ring. In embodiments, the R group may be a phenyl ring, substituted with a second phenyl ring, which in turn is substituted with a third phenyl ring.

In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> is an aromatic group, the aromatic group may be a polycyclic aromatic hydrocarbon, for example, naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene, and/or benzo[c]fluorene. The R group may be bonded to the triphenylene derivative by any isomer of the polycyclic aromatic hydrocarbons described, for example, <NUM>-napthalene, <NUM>-napthalene, <NUM>-anthracene, <NUM>-anthracene. The polycyclic aromatic hydrocarbon group may be substituted with other moieties such as aryl groups, alkyl groups, heteroatoms, and/or other electron withdrawing or electron donating groups.

In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> is an aromatic heterocyclic group, the heterocyclic group may be a three membered ring, a four membered ring, a five membered ring, a six membered ring, a seven membered ring, an eight membered ring, a nine membered ring, a ten membered ring, or a fused ring. In embodiments, the heterocyclic group may be furan, benzofuran, isobenzofuran, pyrrole, indole, isoindole, thiophene, benzothiophene, benzo[c]thiophene, imidazole, benzimidazole, purine, pyrazole, indazole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, pyridine, quinoline, isoquinoline, pyrazine, quinoxaline, acridine, pyrimidine, quinozoline, pyridazine, cinnoline, phthalazine, <NUM>,<NUM>,<NUM>-triazine, <NUM>,<NUM>,<NUM>-triazine, <NUM>,<NUM>,<NUM>-triazine. pyridine or thiophene.

In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> is an aliphatic group, the aliphatic group may be one of, or a combination of, an n-alkyl chain, a branched alkyl chain, an alkyl chain comprising unsaturated moieties, an alkyl chain comprising heteroatoms, for example, fluorine, chlorine, bromine, iodine, oxygen, sulphur, nitrogen. The alkyl chain may comprise unsaturated portions, comprising alkenes, or aromatic moieties. The alkyl chain may comprise functional groups for further derivatisation of the polycyclic aromatic hydrocarbon, e.g. triphenylene, derivative. For example, the functional groups may be one or more of an azide, a carbonyl group, an alcohol, a halogen, or an alkene.

In embodiments, In embodiments wherein R, R<NUM>, R<NUM>, or R<NUM> comprise a crown ether.

The polycyclic aromatic hydrocarbon, e.g. triphenylene, derivatives may be used, for example, as luminescent dyes for use in devices.

A further aspect of the invention provides a device comprising the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives. The device may be an electronic device, for example, an organic electroluminescent device, a thin-film transistor and/or an OPV (organic photovoltaic) device. The electronic device may comprise a digital display, the digital display comprising the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives, of the present invention, for example, a liquid crystal display. The digital display may be in a television screen, a computer monitor, a mobile phone screen, a games console, for example. The organic electroluminescent device may comprise a pair of electrodes and one or more layers interposed therebetween, wherein the one or more layers comprise one or more of the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives.

The device may be for the use of detecting species, for example, ions, e.g. metal ions. For example, the polycyclic aromatic hydrocarbon derivative, e.g. the triphenylene derivative, may comprise a moiety that is capable of binding to a species, e.g. an ion. The moiety may be tagged to or integrated into, i.e. covalently bonded to, the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative. Binding of a species to a polycyclic aromatic hydrocarbon derivative, e.g. a triphenylene derivative, may elicit a luminescent response. The luminescent response may be recorded to quantitatively or qualitatively measure the presence of the species, e.g. in solution. The moiety may be one or more of a crown ether, a multidentate ligand, a bidentate ligand or a monodentate ligand. The moiety may be the R group of the polycyclic aromatic hydrocarbon, e.g. triphenylene, derivatives. The polycyclic aromatic hydrocarbon, e.g. triphenylene, derivative, e.g. comprising a moiety that is capable of binding to a species, e.g. metal ions. The triphenylene derivatives may be spin coated onto a dipstick. The dipstick may comprise a UV LED (light emitting diode). The LED may be illuminated in the presence of specific species upon binding to the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative, e.g. ions, metal ions. The LED illumination may be specific to a specific species that is bound to the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative, i.e. a specific wavelength of light, wavelength A, is emitted by the LED upon binding to a specific species, species A, and a different wavelength of light, wavelength B, is emitted by the LED upon binding to a specific species, species B.

The device may be used in biofluorescent microscopy techniques. The device may comprise the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives, as a luminescent dye that may be used to label or tag biological, or non-biological samples, which may include DNA or proteins or antigens or biomarkers.

The device may comprise a polymer, or a pre-polymer, and/or a resin composition for use in printing, for example, for use in 3D printing plastic products comprising the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives. The polycyclic aromatic hydrocarbon, e.g. triphenylene, derivatives may be used as a dopant in the device.

The polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative(s), of the device may emit light in the visible spectrum, i.e. between <NUM> and <NUM>. The polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative(s), of the device may exhibit a Stokes shift of between <NUM>-<NUM> to <NUM>,<NUM>-<NUM>, for example, between <NUM>,<NUM>-<NUM> to <NUM>,<NUM>-<NUM>. The polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivative(s), of the device may exhibit a conductivity value of <NUM> × <NUM>-<NUM> S cm-<NUM> and <NUM> × <NUM>-<NUM> S cm-<NUM>, for example, between <NUM> × <NUM>-<NUM> S cm-<NUM> and <NUM> × <NUM>-<NUM> S cm-<NUM>. The polycyclic aromatic hydrocarbon derivative, e.g. the triphenylene derivative(s), of the device may) exhibit a photoconductivity when irradiated at <NUM> of between <NUM> × <NUM>-<NUM> S cm-<NUM> and <NUM> × <NUM>-<NUM> S cm-<NUM> , for example, between <NUM> × <NUM>-<NUM> S cm-<NUM> and <NUM> × <NUM>-<NUM> cm-<NUM>.

There is further disclosed a compound for the fabrication of the triphenylene derivatives of claim <NUM> comprising the structure:
<CHM>
wherein A independently represents a hydrogen atom, an aryl group, an alkyl group comprising <NUM> to <NUM> carbons (e.g. <NUM> to <NUM> carbons, or <NUM> to <NUM> carbons, or <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> or <NUM> carbons) or an alkyl ether.

Preferably, in this embodiment A represents an alkyl chain, for example, comprising between <NUM> to <NUM> carbon atoms, e.g. <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, or <NUM> carbon atoms, e.g. A is C<NUM>H<NUM>.

A yet further aspect of the invention provides a method of synthesising polycyclic aromatic hydrocarbon derivatives according to Claim <NUM>.

In this embodiment, (SM1) represents the polycyclic aromatic hydrocarbon core and (P1) represents a triphenylene derivative. In this embodiment, A' represents an alkyl chain comprising between <NUM> to <NUM> carbons, e.g. <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, or <NUM> carbons. In this embodiment, R represents an alkyl chain with one fewer carbon atoms to that of A'. For example, preferably, A' comprises a linear alkyl chain comprising five carbons, i.e. C<NUM>H<NUM> and R comprises a linear alkyl chain comprising four carbons, i.e. C<NUM>H<NUM>. The method may involve the polycyclic aromatic hydrocarbon, e.g. triphenylene, core (SM1) undergoing an intramolecular rearrangement to produce polycyclic aromatic hydrocarbon, e.g. triphenylene, derivative (P1).

The method may comprise the use of a solvent, for example, an inert solvent. The method may comprise heating the polycyclic aromatic core (SM1) under pressure to produce the polycyclic aromatic hydrocarbon derivative (P1).

In embodiments, the method may comprise a catalyst, for example, a transition metal catalyst. The transition metal catalyst may be a rhodium catalyst, e.g. [[CH<NUM>(CH<NUM>)<NUM>CO<NUM>]<NUM>Rh]<NUM>. The method may comprise heating to reflux in the presence of a transition metal catalyst, for example, a rhodium catalyst, e.g. [[CH<NUM>(CH<NUM>)<NUM>CO<NUM>]<NUM>Rh]<NUM> using toluene as the solvent.

Also described (but not claimed) is a method of synthesising polycyclic aromatic hydrocarbon derivatives (P2), the method comprising the general formula:
<CHM>.

The nitrogen atom may be an amine (NH<NUM>) wherein B comprises two hydrogen atoms.

In embodiments, the method of synthesising polycyclic aromatic hydrocarbon derivatives (P3) comprises the general formula:
<CHM>.

In embodiments, (E) represents the reagent, wherein R is an aromatic group and/or an aliphatic group, and group Z may be one of a derivatised oxygen atom e.g. an OH group; a chlorine atom, or a bromine atom, or any good leaving group. Reagent (E) may be an acyl chloride or a carboxylic acid. The method may involve the polycyclic aromatic hydrocarbon core (SM3) and the reagent (E) undergoing an intermolecular coupling reaction to produce the polycyclic aromatic hydrocarbon derivative (P3).

In embodiments, the method of synthesising polycyclic aromatic hydrocarbon derivatives (P4) comprises the general formula:
<CHM>.

In embodiments, the method of synthesising triphenylene derivatives (<NUM>) comprises the general formula:
<CHM>
wherein R independently represents an aromatic group and/or an aliphatic group.

There is also described a method of synthesising polycyclic aromatic hydrocarbon derivatives (P6), comprising the general formula:
<CHM>.

In another aspect of the invention there is provided a method of synthesising polycyclic aromatic hydrocarbon derivatives (P7) in accordance with Claim <NUM>.

The method may comprise synthesising triphenylene derivatives, wherein the triphenylene core starting material comprises the formula:
<CHM>.

A yet further aspect of the invention provides a method of synthesising polycyclic aromatic hydrocarbon derivatives (P8) in accordance with claim <NUM>.

The method may comprise synthesising triphenylene derivatives (P9) comprising the general formula:
<CHM>.

The method of synthesising triphenylene derivatives may comprise use of the starting material with the formula:
<CHM>.

The method may further comprise a transition metal catalyst. The transition metal catalyst may be a rhodium based catalyst. Additionally or alternatively, the transition metal catalyst may be a palladium Pd(ll) catalyst, for example, palladium acetate.

The method may further comprise a reagent to replace, in situ, group Z with a good leaving group.

The reagent (E) may be a carboxylic acid, for example, benzoic acid or a substituted benzoic acid. Alternatively, the reagent (E) may be an acyl chloride, for example, benzyl chloride or a substituted benzyl chloride.

The method may comprise heating the triphenylene core in a solvent, e.g. toluene, to reflux, in the presence of a palladium catalyst, e.g. Pd(OAc)<NUM>, wherein Compound (E) is a carboxylic acid, i.e. Z is an OH group.

The method may further comprise a species to replace group Z with a good leaving group, for example, the species may be (diacetoxyiodo)benzene).

Alternatively, the method may comprise heating the polycyclic aromatic hydrocarbon core, e.g. the triphenylene core, in a solvent, e.g. toluene, to reflux, wherein Compound (E) is an acyl chloride, i.e. Z is a chlorine atom. The method may further comprise heating the reaction mixture to <NUM>.

It is to be understood that the polycyclic aromatic derivatives may be further functionalised to produce analogues. For example, the polycyclic aromatic hydrocarbon derivatives, e.g. the triphenylene derivatives, may undergo bromination, e.g. using Br<NUM>, to add a bromine atom to one or more aromatic carbon atoms. The bromine atom may act as a functional group to undergo further chemical transformations, e.g. to functionalise the polycyclic aromatic hydrocarbon derivatives with a phenol group. In embodiments, J may represent a bromine atom and/or a phenol group. The bromine atom and/or phenyl group may be used to further functionalise the polycyclic aromatic hydrocarbon derivative.

Additionally or alternatively, the alkyl groups of one or more of the alkoxy groups (e.g. the OC<NUM>H<NUM> groups) may be de-alkylated to form hydroxyl (e.g. phenol) groups (e.g. using boron tribromide).

The polycyclic aromatic hydrocarbon derivatives may act as bio-labels or bio-probes.

For the avoidance of doubt, the terms "may", "and/or", "e.g.", "for example" and any similar term as used herein should be interpreted as non-limiting such that any feature so-described need not be present. Indeed, any combination of optional features is expressly envisaged without departing from the scope of the invention, whether or not these are expressly claimed.

Referring now to <FIG>, there is shown a representative structure of a triphenylene derivative series <NUM> according to some embodiments of the invention. In this series, the R group is changed to provide analogues of the triphenylene derivative series <NUM>. As is described in more detail below, the R group may be selected to alter the luminescent and/or other advantageous properties of the triphenylene derivative series <NUM>.

Referring now to <FIG>, there is shown a triphenylene derivative <NUM>, Compound <NUM>, according to an embodiment of the invention. In this embodiment, the R group is an alkyl group of the formula C<NUM>H<NUM>. Referring also to <FIG>, there is shown a schematic synthetic route <NUM> to Compound <NUM>. There is shown two pathways, Pathway A and Pathway B, for a rearrangement reaction of Precursor <NUM>, which is an azide (<NUM>-azido-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)triphenylene), under the reaction conditions of heating in xylene under nitrogen at <NUM> for <NUM>. Pathway B, wherein Precursor <NUM> rearranges to produce a carbazole <NUM>, was expected by the inventors to be successful. However, this is not observed. Instead, and unexpectedly, Pathway A, wherein Precursor <NUM> rearranges to produce Compound <NUM>, was observed.

Without wishing to be bound by theory, it is thought that the reaction Precursor <NUM> in Pathway A proceeds via an intramolecular ring closure mechanism to lead to the formation of Compound <NUM> in quantitative yield. The carbazole <NUM> product was not observed. The method of synthesising Compound <NUM> is described in Example <NUM> below. It should be noted that Compound <NUM> is synthesised using the intramolecular route. We have found that other alkyl analogues (e.g. C7, C8 analogues) can be made in a similar fashion. Other embodiments of the invention require a different method of synthesis, which proceeds via a different chemical mechanism.

Referring now to <FIG>, there is shown a schematic synthetic route <NUM> of the prior art (<NPL>) to produce Precursor <NUM>, and in addition Precursor <NUM>, which is an amine (<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)-<NUM>-triphenylenylamine), and Precursor <NUM>, which is an amine (<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexabutoxy-<NUM>-triphenylenylamine). The full procedures to synthesise Precursor <NUM>, Precursor <NUM>, and Precursor <NUM>, starting from catechol <NUM>, are found in the prior art and are incorporated herein by reference.

Referring now to <FIG>, there is shown a schematic synthetic route 500A for the formation of the triphenylene derivative series <NUM> of the present invention. There is shown Precursor <NUM>, a carboxylic acid <NUM>, and the triphenylene derivative series <NUM>. The carboxylic acid <NUM> comprises an R group, which is incorporated into the oxazole moiety of the triphenylene derivative series <NUM>. The R group may be an alkyl group, or an aryl group, i.e. the carbon atom bonded to the oxazole moiety in the triphenylene derivative series <NUM> may be either sp<NUM> or sp<NUM> hybridised.

The following general procedure may be followed to synthesise the triphenylene derivative series <NUM> using the method 500A of <FIG>. A solution of the appropriate carboxylic acid (<NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford the triphenylene derivative series <NUM>.

This method was based on a prior art method for the formation of a carbazole (<NPL>. ) and, as previously stated, was surprisingly able to form the triphenyl derivative series <NUM>, i.e. the triphenylene oxazole.

Referring also to <FIG> there is shown a schematic synthetic route 500B for the formation of the triphenylene derivative series <NUM> of the present invention. There is shown Precursor <NUM>, an acyl chloride <NUM>, and the triphenylene derivative series <NUM>. There is further shown an intermediate amide 100A. In this method, the acyl chloride <NUM> comprises the R group, which is incorporated into the oxazole moiety of the triphenylene derivative series <NUM>. As with the method 500A of <FIG>, the R group may be an alkyl group, or an aryl group, i.e. the carbon atom bonded to the oxazole moiety in the triphenylene derivative series <NUM> may be either sp<NUM> or sp<NUM> hybridised.

The following general procedure may be followed to synthesise the triphenylene derivative series <NUM> using the method 500B of <FIG>. A solution of Precursor <NUM> or Precursor <NUM> (<NUM>; <NUM> mmol), the appropriate acyl chloride (<NUM> mmol), and triethylamine (<NUM> mmol) in PhMe (<NUM>) was heated at reflux under N<NUM> for <NUM> hours whilst stirring. The resulting solution was further heated at <NUM> for <NUM> minutes. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford the triphenylene derivative series <NUM>.

Without wishing to be bound by theory, the inventors believe that the acyl chloride <NUM> forms an intermediate amide (shown in <FIG> as intermediate amide 100A) with the Precursor <NUM> in situ, which subsequently undergoes a ring closure to form the triphenylene derivative series <NUM>. In contrast to that observed in <FIG> for Compound <NUM>, the reactions of both method 500A and method 500B are intermolecular coupling reactions of the carboxylic acid or the acyl chloride with the Precursor <NUM>. The intermediate amide 100A has been isolated for the method shown in <FIG> when R = Ph.

Advantageously, the methods of <FIG> enable a huge number of analogues of the triphenylene derivate <NUM> to be synthesised by varying the R group of the carboxylic acid <NUM> in the method 500A of <FIG>, or the acyl chloride <NUM> in the method 500B of <FIG>. The triphenylene derivative series <NUM> of the present invention exhibit a number of desirable properties, in particular desirable luminescent characteristics. Advantageously, the R group may be altered to 'tune' these properties. More advantageously, within the known parameters of this invention, the R group may be specifically selected to enable the 'tuning' of the desirable luminescent characteristics. This is demonstrated in detail in the section below.

Referring now to <FIG>, there is shown a schematic synthetic route <NUM> to produce Precursor <NUM>, which is an amine. When R' = C<NUM>H<NUM> then Precursor <NUM> is <NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)-<NUM>,<NUM>-triphenylenediamine. Precursor <NUM> is synthesised from di-nitro triphenylene <NUM>. Di-nitro triphenylene <NUM> is formed as a side product in the prior art method that was used to synthesis the mono-nitro intermediate <NUM> (shown in <FIG>). Di-nitro triphenylene <NUM> may be isolated using flash column chromatography in an earlier fraction than the mono-nitro intermediate <NUM>.

To further exemplify the invention, reference is also made to the following non-limiting Examples.

All compound names were generated using ChemDraw (RTM) software.

Referring to <FIG> there is shown Examples (Compounds <NUM>-<NUM>) of the triphenylene derivative series <NUM>. The methods for synthesising Compounds <NUM>-<NUM> are described below.

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in o-xylene (<NUM>) was added to a flask. This was then heated and held at <NUM> for <NUM> to afford Compound <NUM> (<NUM>% yield).

In the alternative, Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in dry PhMe (<NUM>) was added to a flask containing rhodium octanoate dimer (<NUM>; <NUM> mmol), under a N<NUM> atmosphere. This was then heated and held at reflux for <NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo, the solid was then purified via flash column chromatography (silica; <NUM> % n- hexane: <NUM> % ethyl acetate) to afford Compound <NUM> as a white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-butyl-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, t, J <NUM>) <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, t, J <NUM>), <NUM>- <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. <NUM>C NMR (<NUM>, CDCl3) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+MS m/z: <NUM> ([M+ H]+ <NUM> %), <NUM> ([M+ Na]+ <NUM> %). IR λ-<NUM> (neat): 3112w (C-H), <NUM> (C-H), 1617w (C=N), 1517w (benzene ring), <NUM> (C-O), <NUM> (C-O), <NUM> (C-O) cm-<NUM>. Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM>. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A slurry of benzoic acid (<NUM>; <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. Precursor <NUM> (<NUM>, <NUM> mmol) in PhMe (<NUM>) was added and the reaction was heated and held at reflux for <NUM>. The mixture was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The mixture was washed with <NUM> NaOH (<NUM> × <NUM>) and the organic phase was dried in vacuo. The crude black solid was purified via flash column chromatography (<NUM> % n-hexane: <NUM>% CH<NUM>Cl<NUM>) to afford Compound <NUM> as a white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-phenyltriphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>,s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. <NUM>C NMR (<NUM>, CDCl<NUM>) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+MS m/z: <NUM> ([M]+ <NUM> %), <NUM> ([M+H]+ <NUM> %), <NUM> ([M+Na]+ <NUM> %). Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A solution of <NUM>-naphthalene carboxylic acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-(naphthalen-<NUM>-yl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM> - <NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, t, J <NUM>), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. <NUM>C NMR (<NUM>, CDCl<NUM>) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI+ m/z: <NUM> ([M]+ <NUM>%). IR λ-<NUM> (neat): Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, d, J <NUM>), <NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM> (<NUM>, d, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM>(<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. <NUM>C NMR (<NUM>, CDCl<NUM>) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%). Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A solution of <NUM>-anthracene carboxylic acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-(anthracen-<NUM>-yl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, dd, J <NUM>, <NUM>) <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM>(<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR (<NUM>, CDCl<NUM>) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM><NUM>, <NUM><NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%). Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM>. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A solution of <NUM>-anthracene carboxylic acid (<NUM>; <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in o-xylene (<NUM>) was heated to <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>, <NUM> mmol) in o-xylene (<NUM>) was added and heated to <NUM> for <NUM>. The mixture was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The mixture was washed with <NUM> NaOH (<NUM> × <NUM>) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s) <NUM> (<NUM>, s) <NUM> (<NUM>, s), <NUM> (<NUM>,s) <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t, J6. <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, p, J <NUM>, <NUM>) <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM><NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%). Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>NO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A solution of <NUM>-fluorobenzoic acid (<NUM>; <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in o-xylene (<NUM>) was heated to <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>, <NUM> mmol) in o-xylene (<NUM>) was added and heated to <NUM> for <NUM>. The mixture was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The mixture was washed with <NUM> NaOH (<NUM> × <NUM>) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-fluorophenyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>; CDCl3) δH: <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>) ppm. <NUM>C NMR (<NUM>; CDCl3) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. <NUM>F NMR (<NUM>, CDCl3) δF: -<NUM> ppm. MALDI+ m/z: <NUM> ([M+H+<NUM>]+ <NUM> %), <NUM> ([M+H]+ <NUM> %), <NUM> ([M]+ <NUM> %). IR λ-<NUM> (neat): <NUM> (C-H), <NUM> (C- H), <NUM> (C-H), 1616w (C=N), <NUM> (benzene ring), <NUM> (benzene ring), <NUM> (benzene ring), <NUM> (C-O), <NUM> (C-O) cm-<NUM>.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>; CDCl<NUM>) δH: <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>) ppm. <NUM>C NMR (<NUM>; CDCl<NUM>) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. 19F NMR (<NUM>; CDCl3) δF: -<NUM> ppm. ES+MS m/z: <NUM> ([M+H+Na]+ <NUM>%), <NUM> ([M+Na]+ <NUM>%), <NUM> ([M]+ <NUM>%). IR λ-<NUM> (neat): <NUM> (C-H), <NUM> (C-H), <NUM> (C-H), 1617w (C=N), <NUM> (benzene ring), <NUM> (benzene ring), <NUM> (C-O), <NUM> (C-O) cm-<NUM>. Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>FNO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>; CDCl3) δH: <NUM> (s, <NUM>), <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM>- <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (m,<NUM>) ppm. 13C NMR (<NUM>; CDCl3) δC: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>,<NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>,<NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>,<NUM>, <NUM>, <NUM>, <NUM> ppm. 19F NMR (<NUM>; CDCl3) δF: -<NUM> ppm. MALDI+ m/z: <NUM> ([M+<NUM>+H]+ <NUM> %), <NUM> ([M+H]+ <NUM> %), <NUM> ([M]+ <NUM> %). IR λ-<NUM> (neat): <NUM> (C-H), <NUM> (C- H), <NUM> (C-H), 1617w (C=N), <NUM> (benzene ring), <NUM> (benzene ring), <NUM> (C-O), <NUM> (C-O) cm-<NUM>. Elemental analysis Found: C, <NUM>; H, <NUM>; N, <NUM> %. C<NUM>H<NUM>FNO<NUM> requires C, <NUM>; H, <NUM>; N, <NUM> %.

Compound <NUM> was synthesised using the following method. A slurry of Precursor <NUM> (<NUM>; <NUM> mmol), iodobenzene diacetate (<NUM>; <NUM> mmol) and palladium diacetate (<NUM>; <NUM> mmol) in a mixture of PhMe (<NUM>) and acetic acid (<NUM>) in PhMe (<NUM>) under an N<NUM> atmosphere was heated and held at reflux for <NUM>. The reaction was then cooled to room temperature and washed with <NUM> NaOH (<NUM>; 2x10mL). The organic phase was evaporated to dryness in vacuo. The solid was then purified via flash column chromatography (<NUM> % n-hexane: <NUM> % CH<NUM>Cl<NUM>) to afford Compound <NUM> as a white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-methyl-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, t, J <NUM>), <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol) and trimethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated at reflux under N<NUM> for <NUM>. <NUM>-Thiophenecarbonyl chloride (<NUM>, <NUM> mmol) was added and heated under reflux for <NUM>. The solution was cooled to room temperature and washed with <NUM> HCl (<NUM>) and the organic phase extracted with EtOAc (<NUM> × <NUM>). The organic phase was dried in vacuo and the resultant black solid was heated at <NUM> for <NUM> mins before being cooled to room temperature. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-(thiophen-<NUM>-yl)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, dd, J <NUM>,<NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, dd J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-Cyanobenzoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)benzonitrile.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, d, J <NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, d, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of <NUM>-(trifluoromethyl)benzoic acid carboxylic acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a yellow solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-(<NUM>-(trifluoromethyl)phenyl)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, d, J <NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, d, J8. <NUM>), <NUM>-<NUM> (<NUM>, t, J6. <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>F NMR δF: (<NUM>, CDCl<NUM>) <NUM> (s) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M+H]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-iodobenzoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-iodophenyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, td, J <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, td, J <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM> %).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-chlorobenzoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-chlorophenyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM> %).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-bromobenzoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-bromophenyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, td, J <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, td, J <NUM>, <NUM>, <NUM>) <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) : <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM> %).

Compound <NUM> was synthesised using the following method. A solution of <NUM>-bromovaleric acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-bromobutyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+ m/z: <NUM> ([M+H]+ <NUM>%), <NUM> ([M+H]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Compound <NUM> (<NUM>, <NUM> mmol) in acetone (<NUM>) was heated to <NUM> and stirred under N<NUM>, to this was added a solution of sodium azide (<NUM>, <NUM> mmol) in water (<NUM>) and left stirring under N<NUM> for <NUM>. After this time a precipitate had formed and the solvent was removed under reduced pressure, the precipitate was then filtered under vacumm and dried to give Compound <NUM> as an off white solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-azidobutyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+ m/z: <NUM> ([M+Na]+ <NUM>%).

Compound <NUM> was synthesised using the following method. Compound <NUM> (<NUM>, <NUM> mmol) was dissolved in anhydrous THF (<NUM>) to this mixture potassium thioacetate (<NUM>, <NUM> mmol) was added and stirred under N<NUM> for <NUM>. The organic phase was then extracted with DCM (<NUM>) and washed with water (<NUM> × <NUM>). The organic phase was then dried in vacuo and the solid recrystalised with DCM:methanol (<NUM> : <NUM>). The resultant precipitate was filtered under suction and the solid washed with methanol to give Compound <NUM> as an off white solid (<NUM>, <NUM> %).

The name for Compound <NUM> is S-(<NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)butyl) ethanethioate.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Compound <NUM> (<NUM>, <NUM> mmol), Sodium Tert-butoxide (<NUM>, <NUM> mmol), Potassium Iodide (<NUM>, <NUM> mmol) and Ethylene Glycol (<NUM>, <NUM> mmol) in MeCN (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The crude solid was dissolved with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>) and then HCl (<NUM>, <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(but-<NUM>-en-<NUM>-yl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, ddt, J <NUM>, <NUM>, <NUM>), <NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+ m/z: <NUM> ([M+H]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of decanoic acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and iodobenzene didecanoate (<NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as a white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-nonyl-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM><NUM>, <NUM>, <NUM>, <NUM><NUM>, <NUM>, <NUM>, <NUM> ppm. ES+ m/z: <NUM> ([M+H]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-(dimethylamino)benzoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is N,N-dimethyl-<NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)aniline.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, d, J <NUM>), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, d, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. ES+ m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of <NUM>-nitrobenzoic acid (<NUM>, <NUM> mmol), palladium diacetate (<NUM> mmol) and (diacetoxyiodo)benzene (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated at <NUM> under N<NUM> for <NUM>. A solution of Precursor <NUM> (<NUM>; <NUM> mmol) in PhMe (<NUM>) was added and heated under reflux for <NUM>-<NUM>, whilst stirring. The solution was cooled to room temperature and diluted with CH<NUM>Cl<NUM> (<NUM>). The organic phase was washed with aqueous NaOH (<NUM>; <NUM> × <NUM>), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as an off-white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>-nitrophenyl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>,s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of (diacetoxyiodo)benzene (<NUM>, <NUM> mmol) and acetylsalicylic acid (<NUM>, <NUM> mmol) in toluene (<NUM>) was heated to <NUM> and stirred for <NUM> mins under N<NUM>. Then Precursor <NUM> (<NUM>, <NUM> mmol) was added to form a black solution which was then stirred for a further <NUM> mins. A solution of palladium diacetate (<NUM>, <NUM> mol %) and acetylsalicyclic acid (<NUM>, <NUM> mmol) in toluene (<NUM>) was heated to <NUM> and stirred for <NUM> mins under N<NUM> before being combined with the black solution. The resultant solution was left stirring at <NUM> for <NUM> under N<NUM>. The crude black solution was dried in vaccuo and purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane). The crude material was then evaporated to dryness in vacuo and then dissolved in a mixture of MeCN (<NUM>) and <NUM> NaOH (<NUM>). The solution was heated to <NUM> for <NUM>. After cooling to room temperature the product was acidified using <NUM> HCl (<NUM>) and extracted into CH<NUM>Cl<NUM> (<NUM> × <NUM>). The combined organic layer was evaporated to dryness in vacuo to afford Compound <NUM> as a white solid (<NUM>.

The name for Compound <NUM> is <NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)phenol.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, dd, J8. <NUM>, <NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, ddd, J <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, ddd, J <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method.

Precursor <NUM> was synthesised using the following method. A solution of <NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexabutoxy-<NUM>-nitrotriphenylene (<NUM>, <NUM> mmol), Sodium borohydride (<NUM>, <NUM>. mmol) and Nickel(II) chloride hexahydrate (<NUM>, <NUM> mmol) in a <NUM>/<NUM> mix of MeOH and THF (<NUM>) was stirred at room temperature for <NUM> under N<NUM>. The crude black solid was then filtered and washed with CHCl<NUM> and the filtrate evaporated to dryness in vacuo to afford Precursor <NUM> as a brown solid (<NUM>, <NUM> %).

Precursor <NUM> had the following characterization data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

A solution of Precursor <NUM> (<NUM>, <NUM> mmol), <NUM>-napthoyl chloride (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was heated to and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % CH<NUM>Cl<NUM>: <NUM> % n- hexane) to afford Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentabutoxy-<NUM>-(naphthalen-<NUM>-yl)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, t, J <NUM>), <NUM>-<NUM> (<NUM>, t, J6. <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Precursor <NUM> (<NUM>, <NUM> mmol) and palladium diacetate (<NUM> mmol) in PhMe (<NUM>) was heated at reflux under N<NUM> for <NUM>. <NUM>-flourobenzoyl chloride (<NUM>, <NUM> mmol) was added and heated under reflux for <NUM>. The solution was cooled to room temperature and dried in vacuo and the resultant black solid was heated at <NUM> for <NUM> minutes before being cooled to room temperature. The crude black solid was purified by flash column chromatography (silica; <NUM> % CH<NUM>Cl<NUM>: <NUM> % n-hexane) to afford Compound <NUM> as an off-white solid (<NUM>; <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>-bis(<NUM>-fluorophenyl)-<NUM>,<NUM>,<NUM>,<NUM>-tetrakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d:<NUM>,<NUM>-d']bis(oxazole).

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, td, J <NUM>, <NUM>, <NUM>), <NUM> (<NUM>, m), <NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>,m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>F NMR δF: (<NUM>, CDCl<NUM>) <NUM> (s) ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of <NUM>'-Carboxybenzo-<NUM>-crown-<NUM> (<NUM>, <NUM> mmol), Oxalyl chloride (<NUM>, <NUM> mmol) and Dimethylformamide (<NUM>, <NUM> mmol) was heated and held at reflux for <NUM> minutes under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. A solution of Precursor <NUM> (<NUM>, <NUM> mmol) and N,N-Diisopropylethylamine (<NUM>, <NUM> mmol) in PhMe (<NUM>) was added. The reaction was then heated and held at reflux for <NUM> under N<NUM>. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at <NUM> for <NUM> mins under N<NUM>. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, <NUM> % EtOAc: <NUM> % n-hexane) to afford compound <NUM> as a brown solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-octahydrobenzo[b][<NUM>,<NUM>,<NUM>,<NUM>,<NUM>]pentaoxacyclopentadecin-<NUM>-yl)-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR δH: (<NUM>, CDCl<NUM>) <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d, J <NUM>), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m) ppm. <NUM>C NMR δC: (<NUM>, CDCl<NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> ppm. MALDI m/z: <NUM> ([M]+ <NUM>%).

Compound <NUM> was synthesised using the following method. A solution of Compound <NUM> (<NUM>, <NUM> mmol) in degassed dichloromethane (<NUM>) was stirred in a nitrogen purged <NUM> neck flask under nitrogen atmosphere at -<NUM>. Boron tribromide (<NUM> solution in dichloromethane, <NUM>µL, <NUM> mmol, <NUM> eq) was added via syringe through a Suba-Seal(RTM) and the dark yellow solution was stirred for at room temperature for <NUM>. Water (<NUM>) was added to quench the reaction and the product was extracted with dichloromethane (<NUM>), washed with water (<NUM> × <NUM>) and dried over MgSO<NUM>. The organic phase was evaporated to dryness and purified by column chromatography (Silica: <NUM>% Ethyl acetate : Hexane) to afford Compound <NUM> as a brown solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(pentyloxy)-<NUM>-phenyltriphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-ol.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, dd, J <NUM>, <NUM>), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, s br), <NUM> (<NUM>, t, J <NUM>), <NUM> (<NUM>, t, J <NUM>), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. ES+MS m/z: <NUM> ([M+Na]+ <NUM> %), <NUM> ([M+H+<NUM>]+ <NUM> %), <NUM> ([M+H]+ <NUM> %).

Compound <NUM> was synthesised using the following method. Compound <NUM> (<NUM>, <NUM> mmol) was disolved in dry dichloromethane (<NUM>) and stirred at <NUM> under a nitrogen atmosphere. <NUM> solution of Br<NUM> in dichloromethane (<NUM>, <NUM> mmol) was then added over <NUM> hours (<NUM> × <NUM>) and monitered by TLC. The reaction was quenched by addition of saturated sodium metabisulfate solution (<NUM>). The product was extracted with dichloromethane (<NUM>) washed with water (<NUM> × <NUM>), dried over MgSO<NUM> and evaporated to dryness. The crude product was then purified by column chromatography (Silica <NUM> % dichloromethane : hexane) to yield Compound <NUM> as a yellow solid (<NUM>, <NUM> %).

The name for Compound <NUM> is <NUM>-bromo-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-phenyltriphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisaton data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> (<NUM>, t J <NUM>), <NUM> (<NUM>, t J <NUM>), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm.

Compound <NUM> was synthesised using the following method. Compound <NUM> (<NUM>, <NUM> mmol), K<NUM>CO<NUM> (<NUM>, <NUM> mmol) and Pd(PPh<NUM>)<NUM> (<NUM>, <NUM> mmol) were dissolved in degassed <NUM> : <NUM> tertahydrofuran : Water mix (<NUM>) under nitrogen atmosphere. (<NUM>-hydroxyphenyl)boronic acid (<NUM>, <NUM> mmol) was then added and the reaction was heated to reflux under N<NUM> for <NUM>. The product was extracted with dichloromethane (<NUM>), washed with water (<NUM> × <NUM>) and evaporated to dryness. The crude product was purified by column cromatography (Silica DCM : Hexane) to yield impure Compound <NUM> as a brown solid.

The name for Compound <NUM> is <NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-phenyltriphenyleno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)phenol.

Compound <NUM> had the following characterisation data: TOF LD+ m/z: <NUM> ([M+<NUM>]+ <NUM> %), <NUM> ([M]+ <NUM> %).

Compound <NUM> was synthesised using the following method. Compound <NUM> (<NUM>, <NUM> mmol) was added to a <NUM> neck round bottom flask, which was purged with nitrogen for <NUM> minutes. Dry dichloromethane (<NUM>) was then added via syringe through a Suba-Seal(RTM) and the brown stirring solution was cooled to -<NUM>. Boron tribromide (<NUM> solution in dichloromethane, <NUM>µL, <NUM> mmol, <NUM> equivalents) was added via syringe through a Suba-Seal(RTM) and the reaction was stirred for <NUM>. The reaction mixture was poured over crushed ice and stirred until the ice had fully melted, <NUM> drops of hydrochloric acid (<NUM>) were added and the product was extracted with ethyl acetate, washed with water (<NUM> × <NUM>), and dried over MgSO<NUM> and evaporated to dryness. The crude product was used without further purification.

The name for Compound <NUM> is <NUM>-methyltriphenyleno[<NUM>,<NUM>-d]oxazole-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentaol.

Compound <NUM> had the following characterisation data: ES+MS m/z: <NUM> ([M+<NUM>(OC<NUM>H<NUM>)]+ <NUM> %), <NUM> ([M+( OC<NUM>H<NUM>)]+ <NUM> %), <NUM> ([M]+ <NUM> %).

Crude Compound <NUM> (<NUM>, <NUM> mmol), potassium carbonate (<NUM>, <NUM> mmol), potassium iodide (<NUM>, <NUM> mmol) was dissolved in dry acetonitrile (<NUM>). <NUM>(-<NUM>-Bromoethoxy)-<NUM>-(<NUM>-methoxyethoxy)ethane (<NUM>µL, <NUM> mmol) was then added via pipette and the reaction was heated to reflux and stirred under a CaCl<NUM> drying tube for <NUM> hours. The reaction was cooled to room temperature and the product was extracted with ethyl acetate (<NUM>), washed with water (<NUM> × <NUM>), brine (<NUM> × <NUM>) and dried over MgSO<NUM> to yield crude Compound <NUM> as a brown solid.

The name for Compound <NUM> is <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(<NUM>-(<NUM>-(<NUM>-methoxyethoxy)ethoxy)ethoxy)-<NUM>-methyl-<NUM>-(pentyloxy)triphenyleno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: ES+MS m/z: <NUM> ([M]+ <NUM> %).

Advantageously, Compound <NUM> is water soluble.

Referring now to <FIG>, there is shown a synthetic route <NUM> to Compound <NUM>.

Compound <NUM> was synthesised from Precursor <NUM> in the following method. The starting material to form Precursor <NUM> was obtained using the method described in<NPL>).

Precursor <NUM> was synthesised in the following method. <NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)dibenzo[fg,op]tetracene (<NUM>, <NUM> mmol) was dissolved in diethyl ether (<NUM>) and then acetic acid (<NUM>, <NUM> mmol, <NUM> eqiv) was added and the mixture stirred at room temperature in a nitrogen atmosphere for <NUM> minutes before the addition of fuming nitric acid (<NUM>µL, <NUM> mmol, <NUM> equiv) was added. The reaction mixture was stirred under nitrogen for <NUM> minutes before the further addition of nitric acid (<NUM>µL, <NUM> mmol, <NUM> equiv) and the reaction mixture was left for <NUM> minutes stirring at room temperature. The mixture was then quenched with water (<NUM>) and the organic phase was washed with NaOH (<NUM>, <NUM> × <NUM>) and then dried in vacuo to provide Precursor <NUM> as a black solid (<NUM>, <NUM> %). This was used in the next step with no further purification.

The name for Precursor <NUM> is <NUM>,<NUM>-dimethoxy-<NUM>-nitro-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)dibenzo[fg,op]tetracene.

Precursor <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl3) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>). <NUM>C NMR (<NUM>, CDCl3) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. MALDI+ m/z: <NUM> ([M+H]+ <NUM> %).

Precursor <NUM> was synthesised in the following method. Precursor <NUM> (<NUM>, <NUM> mmol) and NiCl<NUM>. <NUM><NUM>O (<NUM>, <NUM> mmol, <NUM> equivalents) were dissolved in THF:MeOH (<NUM>, <NUM>:<NUM> ratio), to make a yellow solution, and then NaBH<NUM> (<NUM>, <NUM> mmol, <NUM> equivalents) was added over <NUM> minutes. The black reaction mixture was left stirring under a nitrogen atmosphere for40 minutes after which time it was diluted with chloroform and the precipitate was gravity filters to leave a brown organic phase, which was then dried in vacuo to provide Precursor <NUM> as brown solid (<NUM>, <NUM> %).

The name for Precursor <NUM> is <NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)dibenzo[fg,op]tetracen-<NUM>-amine.

Precursor <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl3) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, J = <NUM>, <NUM>, <NUM>, <NUM>). <NUM>C NMR (<NUM>, CDCl<NUM>) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%).

Precursor <NUM> was synthesised in the following method. Precursor <NUM> (<NUM>, <NUM> mmol) was dissolved in dry dichloromethane (<NUM>) and dry acetonitrile (<NUM>). The solution was cooled to <NUM> under a nitrogen atmosphere then tert-butyl nitrite (<NUM>µL, <NUM> mmol, <NUM> equivalents) and TMSN<NUM> (<NUM>µL, <NUM> mmol, <NUM> equivalents) were added and the reaction mixture stirred <NUM> for <NUM> minutes and then at room temperature for <NUM> minutes. The solution was then dried in vacuo and purified via flash column chromatography (silica,<NUM> % DCM, <NUM> % n-hexane) to provide Precursor <NUM> as a while solid (<NUM>, <NUM> %).

The name for Precursor <NUM> is <NUM>-azido-<NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)dibenzo[fg,op]tetracene.

Precursor <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl3) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>). <NUM>C NMR (<NUM>, CDCl3) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>.

Compound <NUM> was synthesised using the following method. Precursor <NUM> (<NUM>; <NUM> mmol) was dissolved in dry toluene (<NUM>) was added to a flask containing rhodium octanoate dimer (<NUM>; <NUM> mmol), under a nitrogen atmosphere. This mixture was then heated to reflux and stirred for <NUM> hours. The reaction was cooled to room temperature and then dried in vacuo, the solid was then purified via flash column chromatography (silica; <NUM> % n-hexane: <NUM> % ethyl acetate) to provide Compound <NUM> as a white solid (<NUM>, <NUM> %).

The name of Compound <NUM> is <NUM>-butyl-<NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)dibenzo[<NUM>,<NUM>:<NUM>,<NUM>]pyreno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl3) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>). <NUM>C NMR (<NUM>, CDCl3) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%).

Precursor <NUM> (<NUM>; <NUM> mmol), benzoyl chloride (<NUM>µL, <NUM> mmol, <NUM> equivalents), and diisopropylehtylamine (<NUM>µL, <NUM> mmol, <NUM> equiv) were dissolved in dry toluene (<NUM>) and the mixture was heated to reflux under a nitrogen atmosphere. The reaction mixture was stirred for <NUM> hour at which point the mixture was dried in vacuo then the solid was heated to <NUM> for <NUM> minutes. The reaction was cooled to room temperature and the solid was then purified via flash column chromatography (silica; <NUM> % DCM, <NUM> % n-hexane) to afford Compound <NUM> a white solid (<NUM>, <NUM> %).

The name of Compound <NUM> is12,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)-<NUM>-phenyldibenzo[<NUM>,<NUM>:<NUM>,<NUM>]pyreno[<NUM>,<NUM>-d]oxazole.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl3) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>). <NUM>C NMR (<NUM>, CDCl3) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. ES+ m/z: <NUM> ([M+H]+ <NUM>%).

Precursor <NUM> (<NUM>; <NUM> mmol) <NUM>-cyanobenzoyl chloride (<NUM>, <NUM> mmol, <NUM> equiv), and diisopropylehtylamine (<NUM>µL, <NUM> mmol, <NUM> equiv) were dissolved in dry toluene (<NUM>) and the mixture was heated reflux under a nitrogen atmosphere. The reaction mixture was stirred for <NUM> hour at which point the mixture was dried in vaccuo then the solid was heated to <NUM> for <NUM> minutes. The reaction was cooled to room temperature and the solid was then purified via flash column chromatography (silica; <NUM> % DCM, <NUM> % n-hexane) to afford Compound <NUM> as a white solid (<NUM>, <NUM> %).

The name of Compound <NUM> is <NUM>-(<NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentakis(pentyloxy)dibenzo[<NUM>,<NUM>:<NUM>,<NUM>]pyreno[<NUM>,<NUM>-d]oxazol-<NUM>-yl)benzonitrile.

Compound <NUM> had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>). <NUM>C NMR (<NUM>, CDCl<NUM>) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. MALDI+ m/z: <NUM> ([M+H]+ <NUM>%).

Compound XX was synthesised using the following method. Compound <NUM> (wherein R'=C<NUM>H<NUM>) shown in <FIG> (<NUM>, <NUM> mmol) was dissolved in dry dichloromethane under a nitrogen atmosphere at <NUM>. <NUM> solution of Br<NUM> in dichloromethane (<NUM>, <NUM> mmol) was then added over <NUM> (<NUM> × <NUM>) and monitered by TLC. The reaction was stired overnight and then quenched by addition of saturated sodium metabisulfate solution (<NUM>). The product was extracted with dichloromethane (<NUM>), washed with water (<NUM> × <NUM>), dried over MgSO<NUM> and evaporated to dryness. The crude product was then purified by column chromatography (Silica <NUM> % dichloromethane : hexane) to yield Compound XX as a yellow solid (<NUM>, <NUM> %).

The name for Compound XX is <NUM>-bromo-<NUM>-nitro-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)triphenylene.

Compound XX had the following characterisation data: <NUM>H NMR (<NUM>, CDCl<NUM>) δH: <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> (<NUM>, s), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m), <NUM> - <NUM> (<NUM>, m) ppm. ES+MS m/z: <NUM> ([M]+ <NUM> %).

It is understood that the method of brominating Compound XX may be applied to the phenoxazoles of the invention, for example, to add further functionality to the molecules.

The triphenylene derivative series <NUM> of the present invention exhibits a number of advantageous properties that are useful in many applications. Some of these advantageous properties are demonstrated below in a non-limiting way.

Referring to <FIG>, there is shown the normalised absorption and emission spectra <NUM> for Compounds <NUM> to <NUM> of Examples <NUM> to <NUM>, and for compound <NUM>. The solvent used to record the spectra was acetonitrile.

There is shown the absorption spectra (designated with the prefix A) for Compounds <NUM> to <NUM> (A1, A2, A3, A4, A5, A6) and the emission spectra (designated with the prefix E) for Compounds <NUM> to <NUM> (E1, E2, E3, E4, E5, E6). The full emission spectrum E6 for Compound <NUM> could not be detected due to equipment limitations.

The absorption spectra A403 and emission spectra E403 of intermediate compound <NUM> shown in <FIG> (<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-hexakis(pentyloxy)triphenylene) was also recorded and used as a reference.

Referring also to Table <NUM>, there is shown luminescent data for the Compounds <NUM> to <NUM>. There is shown the maximum absorption values λmax (nm), the maximum emission values λmax (nm), the pseudo Stokes shift pSS (cm-<NUM>), the quantum yield Φ, and the brightness (M-<NUM> cm-<NUM>). The luminescent data shown in Table <NUM> was recorded for each of the Compounds <NUM> to <NUM> individually in ethyl acetate, octan-<NUM>-ol, and acetonitrile.

Referring also to Table <NUM>, there is shown further luminescent data for Compounds <NUM> to <NUM>. There is shown the molar extinction coefficients (E x <NUM><NUM>) (M-<NUM> cm-<NUM>) alongside the maximum absorption values λmax (nm), recorded at a concentration of <NUM> x <NUM>-<NUM> mol dm-<NUM> individually in ethyl acetate, octan-<NUM>-ol, and acetonitrile.

The triphenylene derivative series <NUM>, which are exemplified as Compounds <NUM> to <NUM>, exhibit many advantageous luminescent properties (as demonstrated by the data in Tables <NUM> and <NUM>, and <FIG>) which are discussed below.

Compounds <NUM> to <NUM> exhibit large Stokes shifts in comparison with many commercially available dyes, e.g. the Alexa Fluor series (<NPL>). It is believed that the Stokes shifts of Compounds <NUM> to <NUM> (Compound <NUM> in particular) are some of the largest Stokes shifts observed for known luminescent organic compounds.

Additionally, the advantageous luminescent properties such as the Stokes shift may be altered or 'tuned' by variation of the R group within the triphenylene derivative series <NUM>.

For example, as shown in Table <NUM> and <FIG>, the maximum absorption wavelength remains relatively constant for each of the Compounds <NUM> to <NUM>. However, the maximum emission wavelength undergoes a red shift as the R group is varied, i.e. the R group is changed from an alkyl group (Compound <NUM>, wherein R=C<NUM>H<NUM>) to a phenyl group (Compound <NUM>, wherein R=Ph) or a polycyclic aromatic hydrocarbon (Compounds <NUM> to <NUM>, wherein R=naphthalene or anthracene). This 'tunable' characteristic is not observed with many other commercially available dyes.

It should be noted that by Stokes shift, we also mean a 'pseudo' Stokes shift. The IUPAC definition of the Stokes shift requires that the difference in the band maxima of the absorption and luminescence arise from the same electronic transition. However, it is widely referred to in the literature in general terms to mean the difference in excitation and emission wavelengths, regardless of electronic transition.

Without wishing to be bound by theory, we believe that the triphenylene derivative series <NUM> of the present invention are push-pull twisted internal charge transfer systems, wherein the triphenylene moiety when substituted with five electron-donating alkoxy groups (shown in <FIG> as C<NUM>H<NUM>), provides a 'push' moiety. The R group provide a 'pull' moiety when conjugatively coupled to the triphenylene moiety by the oxazole unit. Therefore, further stabilisation of the excited state may be achieved by increasing the electron withdrawing nature of the R group. As the energy of the excited state is lowered, this increases the Stokes shift. Advantageously, the triphenylene derivative series <NUM> of the present invention may be tuned to provide this characteristic, as required depending upon the application.

Advantageously, the emission spectra of Compounds <NUM> to <NUM> span a large portion of the visible spectrum. The R group need not be limited to those disclosed, and may be any alkyl or aryl group. In particular, variation of the R group with, for example, a different aromatic hydrocarbon group has been shown to result in a shift in the emission spectra. The shift in emission, and consequently the resulting visible colour of a specific triphenylene derivative, within the triphenylene derivative series <NUM>, may be predicted with a good level of certainty for variation of the R group. Advantageously, this provides a huge number of analogues, for example wherein R is an aryl group, so that the emission is a colour within the visible spectrum, and this visible colour may be 'tuned' by slight structural alteration to the R group of the triphenylene derivative series <NUM> of the present invention.

Compounds <NUM> to <NUM> exhibit very large molar extinction coefficients (E) of over <NUM>,<NUM>-<NUM> cm-<NUM>. This is comparable to commercially available dyes, for example, the Alexa Fluor series, e.g. Alexa Fluor <NUM> has a molar extinction coefficient of <NUM>,<NUM>-<NUM> cm-<NUM>.

Compounds <NUM> to <NUM> also advantageously exhibit high quantum yields Φ and high brightness values. The quantum yield Φ in this case is defined as the ratio of the number of photons emitted to the number of photons absorbed.

Consequently, the Compounds <NUM> to <NUM> exhibit high brightness values, the brightness being defined as the product of the molar extinction coefficient and fluorescence quantum yield.

Additionally, it has surprisingly been found that Compound <NUM> has a quantum yield of <NUM>%.

Referring now to <FIG>, there is shown a graph of the normalised photoemission <NUM> of Compounds <NUM> to <NUM> in the solid state. There is shown the photoemission in the solid state (designated with the prefix ES) for Compounds <NUM> to <NUM> (ES1, ES2, ES3, ES4, ES5, ES6).

Referring also to Table <NUM>, there is shown a comparison of the photoemission of the Compounds <NUM> to <NUM> in the solid state and in ethyl acetate, and the difference between these values Δ.

Advantageously, the photoemission does not substantially change when Compounds <NUM> to <NUM> are dissolved in ethyl acetate in comparison to in the solid state. This demonstrates predictability and stability of photo-emissive behaviour.

Referring to Table <NUM> there is shown the DSC (Differential scanning calorimetry) thermal analysis for Compounds <NUM> to <NUM>.

There is shown the phase transition for each of the Compounds <NUM> to <NUM>, wherein Cr means crystalline, X means an unknown endothermic event, Colh means hexagonal columnar phase, and Colx means unknown liquid crystalline state. This shows that Compounds <NUM> to <NUM> are mesogenic, i.e. have liquid crystallinity.

Referring also to <FIG> there is shown a DSC (Differential scanning calorimetry) thermal analysis plot <NUM> of phase type of Compounds <NUM> to <NUM>, shown for both heating and cooling. The crystalline phase, the unknown solid phase, the columnar hexagonal phase, and the unknown liquid crystal phase are shown.

Referring to Table <NUM> there is shown the values for the average conductivity and the average photoconductivity of Compounds <NUM> to <NUM>, when irradiated at <NUM> at room temperature. The molar absorptivity constant (E<NUM>) at <NUM> in ethyl acetate is also provided. The conductivity and photoconductivity were also recorded for compound <NUM> shown in <FIG>, which is used as a reference.

Advantageously, Compounds <NUM> to <NUM> show an increase in conductivity, i.e. the photoconductivity values, upon light irradiation. The conductivity and the photoconductivity is much higher for the triphenylene derivatives comprising an oxazole moiety, when compared to reference compound <NUM>, which does not comprise an oxazole moiety. More advantageously, the photoconductivity increases significantly when the R group is a polycyclic aromatic hydrocarbon, i.e. for Compound <NUM>, wherein R=Ph, and for Compounds <NUM> and <NUM>, wherein R=naphthalene.

Referring also to <FIG> there is shown a photoconductivity experiment <NUM> for Compound <NUM> in comparison with the reference compound <NUM> (shown in <FIG>). The absorbance spectra <NUM> and emission spectra <NUM> of Compound <NUM> was measured in the presence of phenyl-C61-butyric acid methyl ester (PCBM) at different ratios. The graph <NUM> shows measurements of the electrical conductivity at different temperatures with light irradiation at <NUM> for the reference compound <NUM>. The graph <NUM> shows measurements of the electrical conductivity at different temperatures with light irradiation at <NUM> for Compound <NUM>.

Surprisingly, Compound <NUM> displays improved conductivity, and photoconductivity, when the oxazole moiety is introduced. This is in comparison with the conductivity and photoconductivity of reference compound <NUM>, which does not comprise an oxazole moiety substituted with an R group, as is characteristic of the triphenylene derivative series <NUM> of the present invention.

It has also been shown that compounds within the triphenylene derivative series <NUM> of the present invention do not undergo any appreciable photobleaching. The aforementioned properties make the triphenylene derivatives of the present invention highly suitable for use in solar cells.

Referring now to <FIG>, there is shown a photoconductivity experiment <NUM> for Compound <NUM>. There is shown a graph <NUM>, a graph <NUM>, and a graph <NUM>.

The graph <NUM> shows the electrical conductivity measurements for Compound <NUM> at different temperatures. Electrical conductivity measurements were recorded for Compound <NUM> in the presence and absence of irradiating UV light at <NUM>, and after treatment with HCl in the presence and absence of irradiating UV light at <NUM>.

The graph <NUM> shows the electrical conductivity measurements for Compound <NUM> at different pH values. The electrical conductivity was measured for Compound <NUM>: (i) untreated; (ii) after a first treatment with HCl; (iii) after <NUM> hours; (iv) after a second treatment with HCl; (v) and after treatment with NaOH.

The graph <NUM> shows the electrical conductivity measurements for Compound <NUM> at different pH values. The electrical conductivity was measured for Compound <NUM>: (i) untreated; (ii) after a first treatment with NaOH; (iii) after <NUM> hours; (iv) after treatment with HCl; (v) after a second treatment with NaOH.

Referring now to <FIG>, there is shown a photoconductivity experiment <NUM> for Compound <NUM>. The electrical conductivity was measured for Compound <NUM>: (i) untreated; (ii) untreated in the presence of UV light at <NUM>; (iii) after treatment with NaOH (<NUM> for <NUM> minutes); (iv) after treatment with NaOH (<NUM> for <NUM> minutes) in the presence of UV light at <NUM>.

Referring now to <FIG>, there is shown a photoconductivity experiment <NUM> for Compound <NUM>. The electrical conductivity was measured at different temperatures.

The triphenylene derivatives of the present invention may also be used in a functional layer of an OLED (Organic Light Emitting Diode). It has been shown that the triphenylene derivatives of the present invention may exhibit excellent emitting, charge transporting, and/or charge blocking abilities.

Referring now to <FIG>, there is shown an OLED <NUM>. The OLED <NUM> comprises the following successive layers: a substrate <NUM>, an anode <NUM>, an optional hole transport layer <NUM>, an optional electron blocking layer <NUM>, an emissive layer <NUM>, an optional hole blocking layer <NUM>, an optional electron transport layer <NUM>, and a cathode <NUM>.

Each layer described above may comprise any suitable material known to those skilled in the art, and may comprise more than one type of material or layer. For example, the substrate <NUM> may comprise glass, quartz, polymers, and so on. The thickness is not critical and may be, for example, between <NUM> to <NUM> microns depending on the application of the device. The anode <NUM> may comprise any electrically conductive material, e.g. metal, or a conductive metal oxide such as ITO (indium tin oxide). The hole transport layer <NUM> may comprise, for example, <NUM>,<NUM>-bis[(<NUM>-naphthyphenyl)-amino]biphenyl (NPD). The emissive layer <NUM> may comprise aluminium tris(<NUM>-hydroxyquinoline). The hole blocking layer <NUM> may comprise <NUM>,<NUM>-dimethyl-<NUM>,<NUM>-dipphenyl-<NUM>,<NUM>-phenanthroline (bathocuproine, BCP). The electron transport layer <NUM> may comprise, for example, metal chelates such as, for example, aluminium tris(<NUM>-hydroxyquinoline). The cathode <NUM> may comprise any metal, for example, aluminium, lithium, magnesium, and/or calcium.

The emissive layer <NUM> comprises the triphenylene derivatives of the present invention, e.g. the triphenylene derivative series <NUM>.

An OLED <NUM> may be fabricated in the following manner:.

It will be appreciated by those skilled in the art that several variations to the aforementioned embodiments are envisaged without departing from the scope of the invention as defined in the appended claims. For example, the R group of the triphenylene derivative series <NUM> and Precursors <NUM> and <NUM> need not be restricted to C<NUM>H<NUM>, and may be any stable alkyl or aryl group capable of alkylating the phenol moiety of the triphenylene moiety.

Advantageously, the triphenylene derivative series <NUM> of the present invention may be further functionalised, for example, by derivatisation of functional groups within the R group. This provides the possibility of using the triphenylene derivative of the present invention as biotags or probes, for example.

Claim 1:
Polycyclic aromatic hydrocarbon derivatives represented by the following general formula:
<CHM>
wherein R independently represents an aromatic group and/or an aliphatic group; p is an integer of <NUM> to <NUM>;
q and s are independently integers of <NUM> to <NUM>;
Y<NUM>, Y<NUM>, and Y<NUM> independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, OH, a carboxylic acid group, a glycol, an alkoxy, a thioalkoxy, an amino, an acetate, an amide, a thioamide, a thioester, an azo, a silyl group, an alkylated nitrogen atom, a cyano group, a nitro group, an alkyl group (e.g. branched or straight chain alkyl group) and/or an aryl group (e.g. a phenol group).