PATENT CLAIM ANALYSIS

Application Number: 15780635
Application Type: Utility
Filing Date: 2018-09
Publication Date: 2019-02
Patent Classification: ["546", "070000"]

Abstract:
The present invention discloses a fluorescent compound having a sensing ability to aniline and o-toluidine, a preparation method thereof, a preparation method and application of a fluorescent sensing film. The compound contains a naphthalenediimide (NDI) unit, two alkynyl aniline conjugate fragments and two long alkyl chain fragments; compared with perylene anhydride (PDI), naphthalenediimide (NDI) has better solubility, rich photophysical property, good photochemical stability and strong π-π stacking effect; these building units make the prepared fluorescent compound have supramolecular characteristics and more abundant gelling behavior and assembly behavior. Therefore, the sensing film prepared with the fluorescent compound is controllable in the microstructure, good in stability, high in sensitivity, long in service life and able to be repeatedly used. The present invention achieves the sensitive detection of aniline, and more importantly, the detection is completely reversible, so as to lay the solid foundation for the realization of aniline fluorescence sensor.

Claim (Index 2):
A method for preparing a fluorescent compound having a sensing ability to aniline and o-toluidine, which comprises steps of:\n (1) preparing a first compound, which comprises: dissolving 1,4,5,8-naphthalenetetracarboxylic dianhydride and dibromo isocyanuric acid into oleum with a concentration of 20%, respectively, and then sufficiently uniformly stirring at room temperature, adding the oleum dissolved with the dibromo isocyanuric acid into the oleum dissolved with the 1,4,5,8-naphthalenetetracarboxylic dianhydride drop by drop, and then continuously stirring and reacting at 60-90\u00b0 C. for 12-48 h, obtaining a mixed solution, uniformly stirring after pouring the mixed solution into crushed ice, and then sucking and filtering, washing, drying, and obtaining the first compound; (2) preparing a second compound, which comprises: dissolving the first compound into glacial acetic acid under nitrogen protection, and then uniformly stirring at room temperature, and then adding a compound R, reflux-stirring for 2-4 h, filtering and collecting a precipitate, dissolving the precipitate into ice water and sufficiently stirring, and then sucking and filtering, washing, drying, performing column chromatography separation, and obtaining the second compound, wherein: a structural formula of the second compound is a structural formula of the compound R is (3) preparing a third compound, which comprises: dissolving the second compound, P-alkyl aniline, tetrakistriphenylphosphine palladium and cuprous iodide into a mixed solvent of toluene and diisopropylamine under water-free and oxygen-free condition, and then stirring and reacting at 50-70\u00b0 C. for 24-48 h, respectively extracting with saturated sodium chloride aqueous solution and water for many times, spin-drying, performing column chromatography separation, and obtaining the third compound; (4) preparing a fourth compound, which comprises: dissolving methyl trihydroxybenzoate into N,N-dimethylformamide under water-free and oxygen-free condition, and then adding potassium carbonate and potassium iodide in sequence, adding brominated alkane reagent after stirring at 80-120\u00b0 C. for 30 min, continuously reflux-stirring for 24-48 h, filtering and collecting a precipitate, sucking, filtering and washing the precipitate, obtaining a filtrate, refrigerating the filtrate, and then separating white solid out, and obtaining the fourth compound; (5) preparing a fifth compound, which comprises: dissolving the fourth compound into ethanol, and then adding potassium hydroxide, reflux-stirring and reacting for 8-12 h, diluting a stirred and reacted solution with water, adjusting a pH value to 1, filtering and collecting a precipitate, sucking, filtering, washing and drying the precipitate, and obtaining the fifth compound; (6) preparing a sixth compound, which comprises: adding the fifth compound into toluene under nitrogen protection, and then adding a catalytic amount of thionylchloride (SOCl 2 ), reflux-stirring and reacting for 4 h, and then removing excess thionylchloride (SOCl 2 ) and toluene, and obtaining the sixth compound; and (7) preparing the fluorescent compound having the sensing ability to the aniline and the o-toluidine, which comprises: dissolving the sixth compound, N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (EDC) and 4-dimethylaminopyridine (DMAP) into redistilled toluene solution under nitrogen protection, and then adding the third compound after stirring and reacting for 30 min, continuously stirring and reacting at room temperature for 12-20 h, and then washing with water, obtaining a reacted solution, drying after removing solvent from the reacted solution, performing column chromatography separation, and finally obtaining the fluorescent compound having the sensing ability to the aniline and the o-toluidine.

Metadata:
- Claim Count in Document: 15.0
- Percentile: 97.0
- Lexical Diversity: 1.80208
- Patent Class: 546.0
- Transitional Phrase Type: none
- Component Type: 0
- Foreign Priority: True
- Related Applications: ['15156945', '12434753', '12337701', '12964645', '12634757']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7744267799318609
- 35 USC 102 Novelty (BERT): 0.4912662109869979
- Combined Prediction Score: 0.7461107230373747
- Mean Citation Score: 188.343376
- Max Citation Score: 199.20273
- Similarity Product: 133.74433508166254

Labels:
- Claim Label 101: 1
- Claim Label 102: 0
- Claim Label 103: 1
- Claim Label 112: 0
- Combined Label: 0
- Label 101 Adjusted: 1

Dataset: test