Source: http://www.google.com/patents/US7830702?dq=7,117,286
Timestamp: 2016-08-28 08:48:03
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Matched Legal Cases: ['Application No. 60', 'Application No. 03741037', 'Application No. 02725096', 'Application No. 2003281730', 'Application No. 166566', 'Application No. 02725096', 'Application No. 2004']

Patent US7830702 - Synthetic molecular spring device - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsSynthetic molecular spring device featuring: (a) a synthetic molecular assembly, SMA, each scalable chemical module including: (i) at least one atom, M, (ii) at least one complexing group, CG, complexed to an atom, M, (iii) at least one axial ligand, AL, reversibly physicochemically paired with at least...http://www.google.com/patents/US7830702?utm_source=gb-gplus-sharePatent US7830702 - Synthetic molecular spring deviceAdvanced Patent SearchPublication numberUS7830702 B2Publication typeGrantApplication numberUS 10/468,840PCT numberPCT/US2002/007178Publication dateNov 9, 2010Filing dateMar 12, 2002Priority dateMar 12, 2001Fee statusLapsedAlso published asCA2440561A1, DE60220994D1, DE60220994T2, EP1368579A2, EP1368579A4, EP1368579B1, US20040096860, WO2002073062A2, WO2002073062A3, WO2002073062B1Publication number10468840, 468840, PCT/2002/7178, PCT/US/2/007178, PCT/US/2/07178, PCT/US/2002/007178, PCT/US/2002/07178, PCT/US2/007178, PCT/US2/07178, PCT/US2002/007178, PCT/US2002/07178, PCT/US2002007178, PCT/US200207178, PCT/US2007178, PCT/US207178, US 7830702 B2, US 7830702B2, US-B2-7830702, US7830702 B2, US7830702B2InventorsRoie Yerushalmi, Avigdor ScherzOriginal AssigneeYeda Research And Development Co. Ltd.Export CitationBiBTeX, EndNote, RefManPatent Citations (23), Non-Patent Citations (75), Classifications (20), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetSynthetic molecular spring device
US 7830702 B2Abstract
Synthetic molecular spring device featuring: (a) a synthetic molecular assembly, SMA, each scalable chemical module including: (i) at least one atom, M, (ii) at least one complexing group, CG, complexed to an atom, M, (iii) at least one axial ligand, AL, reversibly physicochemically paired with at least one atom, M, complexed to a complexing group, CG, (iv) at least one substantially elastic molecular linker, ML, having body and two ends with at least one chemically bonded to another component of SMA; (b) activating mechanism, AM, operatively directed to an atom-axial ligand pair, whereby following activating mechanism, AM, sending activating signal, AS/AS′, to an atom-axial ligand pair for physicochemically modifying the atom-axial ligand pair, there is activating at least one cycle of spring-type elastic reversible transitions between contracted and expanded linear conformational states of molecular linker, ML. Optionally includes (v) chemical connectors, CC, and/or, (vi) binding sites, BS.
This application is a National Phase Application of PCT/US02/07178 International Filing Date 12 Mar. 2002, which claims priority from U.S. Provisional Patent Application No. 60/274,635 filed 12 Mar. 2001.
The present invention relates to synthetic molecular level devices, such as synthetic molecular springs, engines, and, machines and, more particularly, to a synthetic molecular spring device. The synthetic molecular spring device of the present invention, generally featuring a synthetic molecular assembly and an activating mechanism, exhibits multi-parametric controllable spring-type elastic reversible function, structure, and behavior, operable in a wide variety of different environments. Different types of the primary components, that is, the synthetic molecular assembly and the activating mechanism, of the synthetic molecular spring device, may be selected from a wide variety of corresponding groups and sub-groups, while preserving the controllable spring-type elastic reversible function, structure, and behavior.
In recent years, an increasing number of works and attempts to design, develop, and, implement, such molecular devices have been presented. Several such teachings are: Bissell, R. A., Cordova, E., Kaifer, A. E., and, Stoddart, J. F., “A Chemically and Electrochemically Switchable Molecular Shuttle”, Nature 369, 133-137 (1994); Feringa, B. L., “In Control Of Molecular Motion”, Nature 408, 151-154 (2000); Jimenez, M. C., Dietrich-Buchecker, C., and Sauvage, J. P., “Towards Synthetic Molecular Muscles: Contraction and Stretching of a Linear Rotaxane Dimer”, Angewandte Chemie-International Edition in English 39, 3284-3287 (2000); Mahadevan, L. and Matsudaira, P., “Motility Powered by Supramolecular Springs and Ratchets”, Science 288, 95-99 (2000); Otero, T. F. and Sansinena, J. M., “Soft and Wet Conducting Polymers for Artificial Muscles”, Advanced Materials 10, 491-494 (1998); and, Tashiro, K., Konishi, K., and Aida, T., “Metal Bisporphyrinate Double-Decker Complexes as Redox-Responsive Rotating Modules, Studies on Ligand Rotation Activities of the Reduced and Oxidized Forms Using Chirality as a Probe”, Journal of the American Chemical Society 122, 7921-7926 (2000).
These teachings relate to such molecular structures in the form of rotaxane molecules, catenanes molecules, polypyrrole films, single-walled nanotube sheets, among others. Several teachings relating specifically to rotaxane molecules and/or catenanes molecules are: Leigh, D. A., Troisi, A., and, Zebetto, F., “A Quantum-Mechanical Description of Macrocyclic Ring Rotation in Benzylic Amide [2]Catenanes”, Chemistry European Journal 7, 1450-1454 (2001); Amendola, V., Fabbrizzi, L., Mangano, C., and, Pallavicini, P., “Molecular Machines Based on Metal Ion Translocation”, Accounts of Chemical Research 34, 488-493 (2001); Collin, J. P., Dietrich-Buchecker, C., Gavina, P., Jimenez-Molero, M., and, Sauvage, J. P., “Shuttles and Muscles: Linear Molecular Machines Based on Transition Metals”, Accounts of Chemical Research 34, 477-487 (2001); Ashton, P. R. et al., “Dual Mode ‘Co-Conformational’ Switching in Catenanes Incorporating Bipyridinium and Dialkylammonium Recognition Sites”, Chemistry European Journal 7, 3482-3493 (2001); and, Cardenas, D. J. et al., “Synthesis, X-ray Structure, and Electrochemical and Excited-State Properties of Multicomponent Complexes Made of a [Ru(Tpy)2]2+Unit Covalently Linked to a [2]-Catenate Moiety. Controlling the Energy-Transfer Direction by Changing the Catenate Metal Ion”, Journal of the American Chemical Society 121, 5481-5488 (1999).
Thus, a molecular structure, in the form of a chemical unit or module, featuring an interrelating collection of components and/or elements, that has the ability to store energy of predetermined chemical bonds in a particular molecular conformation, and convert the stored energy into mechanical motion, may be regarded as a molecular engine. In order to use such a molecular module as a whole or part of a molecular engine, it is necessary to control its action. One possibility relies on conditional formation and breakage of chemical bonds. Here, formation and breakage of chemical bonds translates to storage and release of potential energy, and concomitant molecular mechanical motion or movement. Although, it is quite common to find terms such as ‘molecular machines’, ‘molecular engines’, ‘molecular springs’, and other similar terms related to molecular structures and assemblies, practical implementation of the related mechanical properties, currently, is generally far from being demonstrated, for example, as highlighted by Amendola, V. et al., “Molecular Events Switched by Transition Metals”, Coordination Chemistry Reviews 190, 649-669 (1999).
The present invention relates to a synthetic molecular spring device. The synthetic molecular spring device, generally featuring a synthetic molecular assembly and an activating mechanism, exhibits multi-parametric controllable spring-type elastic reversible function, structure, and behavior, operable in a wide variety of different environments. Different types of the primary components, that is, the synthetic molecular assembly and the activating mechanism, of the synthetic molecular spring device, may be selected from a wide variety of corresponding groups and sub-groups, while preserving the controllable spring-type elastic reversible function, structure, and behavior.
The present invention relates to a synthetic molecular spring device. It is noted herein, that the present invention relates to and is focused on a ‘synthetic’ molecular spring device, based on components and elements which are synthetically made and/or modified using techniques of synthetic chemistry, in contrast to ‘natural’ molecular spring devices, based on components and elements naturally existing in the form of molecular structures and assemblies, such as naturally existing ‘biochemical’ or ‘molecular biological’ types of molecular structures and assemblies which may, under specified conditions, be considered to exhibit properties and functions of a molecular spring device.
Capability of fast, for example, in the case of photoexcitation, as well as slow, for example, in the case of pH control, time scale functioning of the synthetic molecular spring device. No chemical, or other by-products are generated during the working cycle. The working cycle is based on reversible processes. This property is highly important for a molecular device to be able to operate in a continuous and efficient manner. The modular functional/structural approach provides a variety of activating and controlling means. Thus, it is possible to control the synthetic molecular spring device in accordance with specific properties and characteristics of the individual components. For example, it is possible to activate a [Ni]Porphyrin based the synthetic molecular spring device by photoexcitation, electro-reduction/oxidation, or, by a chemical manipulation such as introducing a monodentate ligand into the synthetic molecular assembly of the synthetic molecular spring device. In a similar synthetic molecular spring device based on [Zn]Porphyrin, only chemical control is accessible, thereby providing selectivity with respect to implementing the synthetic molecular spring device. It is possible to operate various embodiments of the synthetic molecular spring device in different environments. For example, it is possible to introduce hydrophilic or hydrophobic substituents in peripheral positions of the synthetic molecular assembly, in order to make the synthetic molecular assembly more water or organic soluble. The intrinsic functions of the synthetic molecular spring device, via the expansion/contraction transitions are generally not sensitive to the solvent environment. The induced motion of the molecular linker in the synthetic molecular assembly of the synthetic molecular spring device is not based on a thermal fluctuation type of phenomenon, such as that described by Asfari, Z. and Vicens, J., “Molecular Machines”, Journal of Inclusion Phenomena and Macrocyclic Chemistry 36, 103-118 (2000). Spectroscopic techniques, and, more ‘mechanical’ types of monitoring techniques, for example, Atomic Force Microscopy, can be used in order to monitor operation of the synthetic molecular spring device. The synthetic molecular spring device of the present invention is operable under variable operating conditions and in a variety of different environments, part of or coupled to and interactive with the macroscopic world. For example, as part of implementing the synthetic molecular spring device, the synthetic molecular assembly may be used as an entity in a state of matter selected from the group consisting of the solid state, the liquid state, the gas state, and, combinations thereof, for performing mechanical work at the molecular level, for mechanically altering the conformation of a substrate molecule, or, any other manipulation at the molecular level. In particular, the synthetic molecular assembly may be used in a variety of modes physicochemically interactive with a substrate, where the substrate is, for example, a molecular or macromolecular entity, or, a composite of atoms.
Transition from a contracted to an expanded linear conformational state, or, from an expanded to a contracted linear conformational state, of a predetermined molecular linker (ML) is characterized by a parameter, herein, referred to as the molecular linker inter-end effective distance change, DE-DC, or, DC-DE, respectively, indicating the sign, that is, positive or negative, respectively, and, the magnitude, of the change of the ‘effective’ distance, D, between the two ends of a single molecular linker (ML), or, between two arbitrarily selected ends of a plurality of molecular linkers (ML), included in a particular synthetic molecular assembly (SMA), following the respective transition in linear conformational states. For this parameter, DC refers to the molecular linker inter-end effective distance, D, when the synthetic molecular assembly (SMA), is in a contracted linear conformational state, and, DE refers to the molecular linker inter-end effective distance, D, when the synthetic molecular assembly (SMA), is in an expanded linear conformational state.
It is especially noted that the term ‘reversibly physicochemically paired’ used for describing an axial ligand, AL, reversibly physicochemically paired with an atom, M, means that the axial ligand, AL, and the atom, M, are capable of reversibly physicochemically debonding or dissociating from each other, to a controllable extent or degree, and, bonding to, or associating with, each other, to a controllable extent or degree, following the activating mechanism, AM, sending an activating signal, AS/AS′, to a predetermined atom-axial ligand pair, that is, to an atom-axial ligand ‘bonded’ pair, or, to an atom-axial ligand ‘non-bonded’ pair, for physicochemically modifying, that is, for ‘debonding’ the atom-axial ligand bonded pair, to a controllable extent or degree, or, for ‘bonding’ the atom-axial ligand non-bonded pair, to a controllable extent or degree, respectively, as illustrated by (A) and (B), respectively, in FIGS. 1-5.
Accordingly, for implementing the synthetic molecular spring device of the present invention, an operator operates and controls the activating mechanism, AM, for sending an activating signal, AS/AS′, to ‘either’ the atom-axial ligand ‘bonded’ pair, or, to the atom-axial ligand ‘non-bonded’ pair, for physicochemically modifying, that is, for ‘debonding’ the atom-axial ligand bonded pair, to a controllable extent or degree, or, for ‘bonding’ the atom-axial ligand non-bonded pair, to a controllable extent or degree, respectively, thereby activating at least one cycle of spring-type elastic reversible transitions between contracted and expanded linear conformational states of a predetermined molecular linker, ML.
In the immediately preceding five exemplary preferred embodiments of the generalized synthetic molecular spring device, this type of controllable reversible debonding and bonding, or, bonding and debonding, process, is generally referred to along with use of the phrase ‘activating at least one cycle of spring-type elastic reversible transitions between a contracted linear conformational state (A) and an expanded linear conformational state (B) of the molecular linker, where the linear conformational states (A) and (B) are appropriately illustrated in each accompanying drawing.
In general, the first or second type of region of physicochemical behavior of the axial ligand, AL, may correspond to an ‘end’ or ‘terminal’ region of the axial ligand, AL, or, an ‘intermediate’ region of the axial ligand, AL. For example, in the particular case where the axial ligand; AL, is of a linear or branched geometrical configuration or form, the first or second type of region of physicochemical behavior of the axial ligand, AL, may correspond to an ‘end’ or ‘terminal’ region of the axial ligand, AL. In the particular case where the axial ligand, AL, is of a cyclic geometrical configuration or form, the first or second type of region of physicochemical behavior of the axial ligand, AL, necessarily corresponds to an ‘intermediate’ region of the axial ligand, AL, since, unless arbitrarily defined or assigned, a cyclic axial ligand has no ‘end’ or ‘terminal’ region.
The conformational analyses of the molecular systems indicated in the table, including the structural and orbital arrangements as well as property calculations, were carried out using a variety of computational techniques for comparative purposes, using GAUSSIAN98. The hybrid density functional (HDFT) technique used is B3LYP, which employs the Lee-Yang-Parr correlation functional in conjunction with a hybrid exchange functional first proposed by Becke. The Hay and Wadt relativistic effective core potentials (RECP) were used for the transition metal. The specific effective core potential/basis set combination chosen was LANL2DZ (Los Alamos National Laboratory 2-double-ζ; the ‘2’ indicating that the valence and ‘valence-1’ shells are treated explicitly). The LANL2DZ basis set is of double-ζ quality in the valence and ‘valence-1’ shells, whereas the RECP contains Darwin and mass-velocity contribution. For more accurate properties, fine-integration grid, tight single point property calculations were carried out using a larger basis set denoted LANL2DZ+1, which consists of the LANL2DZ basis set augmented with single f functions on Ni, and the standard Dunning's cc-pvdz (correlation consistent polarized valence double-ζ) basis set ([4s3p1d/3s2p1d/2s1p]) on first and second row atoms.
A second function, related to the primary function, of the molecular linker, ML, is for serving as a physical geometrical linear spacer as part of designing and synthesizing the geometrical configuration or form and dimensions, with respect to the contracted and expanded linear conformational states of the synthetic molecular assembly, SMA. The molecular linker, ML, is the primary component of the synthetic molecular assembly, SMA, which determines the extent or degree of transition from the contracted to the expanded linear conformational state, or, from the expanded to the contracted linear conformational state. As previously described above, this extent or degree of transition is characterized by the parameter, the molecular linker inter-end effective distance change, DE-DC, or, DC-DE, respectively, indicating the sign, that is, positive or negative, respectively, and, the magnitude, of the change in the inter-end ‘effective’ distance, D, between the two ends of a single molecular linker, ML, or, between two arbitrarily selected ends of a plurality of molecular linkers, ML, included in a particular synthetic molecular assembly, SMA, following the respective transition in linear conformational states.
A second function of the binding site, BS, is for providing directed modularity in the scale-up assembly of a ‘poly-molecular’ synthetic molecular assembly, SMA, featuring a plurality of chemical units or modules. By defining specific threading or linking possibilities, for example, according to a building block type of scaled-up assembly, it is possible to predetermine the type and configuration of connectivity, of a bottom-up self-assembly of large, poly-molecular structures of the synthetic molecular assembly, SMA, featuring a plurality of chemical units or modules.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS3556553Apr 1, 1968Jan 19, 1971Kolbe JoachimPolyurethane cushion support for vehiclesUS4412675Jul 27, 1981Nov 1, 1983Mitsubishi Pencil Co., Ltd.Carbon spring and process for preparing the sameUS4588638Apr 19, 1985May 13, 1986The Dow Chemical CompanyDunnage materialUS4848511Jul 15, 1988Jul 18, 1989Nippon Zeon Co., Ltd.Vibration insulating rubberUS5464987Sep 2, 1994Nov 7, 1995Hitachi, Ltd.Method for constructing a carbon molecule and structures of carbon moleculesUS5900405Jun 7, 1995May 4, 1999Bioelastics Research, Ltd.Polymers responsive to electrical energyUS6212093 *Jan 14, 2000Apr 3, 2001North Carolina State UniversityHigh-density non-volatile memory devices incorporating sandwich coordination compoundsUS6243248Jul 23, 1999Jun 5, 2001International Business Machines CorporationMolecular arrangement and switching deviceUS6324091Jan 14, 2000Nov 27, 2001The Regents Of The University Of CaliforniaTightly coupled porphyrin macrocycles for molecular memory storageUS20030107927Jul 31, 2002Jun 12, 2003Yeda Research And Development Co. Ltd.Method using a synthetic molecular spring device in a system for dynamically controlling a system property and a corresponding system thereofUS20040011821Apr 16, 2003Jan 22, 2004Valois S.A.Fluid dispenser pumpUS20040096860Mar 12, 2002May 20, 2004Roie YerushalmiSynthetic molecular spring deviceUS20080232156Feb 25, 2008Sep 25, 2008Yeda Research And Development Co. Ltd.Method using a synthetic molecular spring device in a system for dynamically controlling a system property and a corresponding system thereofEP1215613A1Dec 15, 2000Jun 19, 2002Clair James J. Dr. LaA digital molecular integratorEP1368579A2Mar 12, 2002Dec 10, 2003YEDA RESEARCH &amp; DEVELOPMENT COMPANY, LTD.Synthetic molecular spring deviceWO1999040812A1Feb 11, 1999Aug 19, 1999Board Of Trustees Operating Michigan State University -Micro-fastening system and method of manufactureWO2000022101A2Oct 13, 1999Apr 20, 2000Cornell Research Foundation, Inc.Enzymes as a power source for nanofabricated devicesWO2000044094A1Jan 20, 2000Jul 27, 2000University Of South CarolinaMolecular computerWO2001044302A2Dec 12, 2000Jun 21, 2001Michael ZeppezauerNanoscaled functional layerWO2001049984A2Dec 20, 2000Jul 12, 2001Bioelastics Research, Ltd.Acoustic absorption polymers and their methods of useWO2001081446A1Apr 23, 2001Nov 1, 2001Bio MerieuxElectroactive complex, electroactive probe and preparation methodWO2002073062A2Mar 12, 2002Sep 19, 2002Yeda Research Development Co. Ltd.Synthetic molecular spring deviceWO2004011821A2Jul 24, 2003Feb 5, 2004Yeda Research And Development Co. Ltd.Synthetic molecular spring device* Cited by examinerNon-Patent CitationsReference1Amendola et al. "Molecuar Movements and Translocations Controlled by Transition Metals and Signaled by Light Emission", Structure and Bonding, 99: 80, 2001.2Amendola et al. "Molecular Events Switched by Transition Metals", Coordination Chemistry Reviews, 190-192: 649-669, 1999.3Amendola et al. "Molecular Machines Based on Metal Ion Translocation", Accounts of Chemical Research, 34(6): 488-493, 2001.4Asakawa et al. "Current/Voltage Characteristics of Monolayers of Redox-Switchable [2]Catenanes on Gold", Adv. Mater., 12(15): 1099-1102, 2000.5Asfari et al. "Molecular Machines", J. Inclusion Phenomena and Macrocyclic Chemistry, 36: 103-118, 2000.6Ashton et al. "Dual-Mode 'Co-Conformational' Switching in Catenanes Incorporating Bipyridinium and Dialkylammonium Recognition Sites", Chem. Eur., 7(16): 3482-3493, 2001.7Ashton et al. "Dual-Mode ‘Co-Conformational’ Switching in Catenanes Incorporating Bipyridinium and Dialkylammonium Recognition Sites", Chem. Eur., 7(16): 3482-3493, 2001.8Ballardini et al. "Molecular-Level Artificial Machines Based on Photoinduced Electron-Transfer Processes", Structure & Bonding, 99: 174-183, 2001.9Balzani et al. "Artificial Molecular Machines", Angew. Chemie Int. Ed., 39: 3348-3391, 2000.10Balzani et al. "Photochemistry and Photophysics of Ru(II)-Polypyridine Complexes in the Bologna Group. From Early Studies to Recent Developments", Coordination Chemistry Reviews, 211: 97-115, 2001.11Bampos et al. "Metalloporphyrin Oligomers With Collapsible Cavities: Characterisation and Recognition Properties of Individual Atropisomers", Chem. Eur. J., 4(2): 335-345, 1998.12Baughman et al. "Conducting Polymer Electromechanical Actuators", Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, p. 559-582, 1990.13Bissell et al. "A Chemically and Electrochemically Switchable Molecular Shuttle", Nature, 369: 13-137, 1994.14Bredas et al. "Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics", Applied Sciences 182, 1996.15Brouwer et al. "Photoinduction of Fast, Reversible Translational Motion in a Hydrogen-Bonded Molecular Shuttle", Science, 291: 2124-2128, 2001.16Buchler et al. "Oxidation and Reduction of Cerium(IV) Sandwich Complexes With Porphyrin Ligands Linked by Aliphatic Diether Bridges of Variable Chain Length", Eur. J. Inorg. Chem., p. 445-449, 1998.17Cardenas et al. "Synthesis, X-Ray Structure, and Electrochemical and Exited-State Properties of Multicomponent Made of a [Ru(Tpy)2]2+ Unit Covalently Linked to a [2]-Catenate Moiety. Controlling the Energy-Transfer Direction by Changing the Catenate Metal Ion", J. Am. Chem. Soc., 121: 5481-5488, 1999.18Chia et al. "Working Supramolecular Machines Trapped in Glass and Mounted on a Film Surface", Angew. Chemie Int. Ed., 40(13): 2447-2451, 2001.19Collin et al. "Construction of One-Dimensional Multicomponent Molecular Arrays: Control of Electronic and Molecular Motions", Eur. J. Inorg. Chem., p. 1-14, 1998.20Collin et al. "Shuttles and Muscles: Linear Molecular Machines Based on Transition Metals", Acc. Chem. Res., 34(6): 477-487, 2001.21Collman et al. "Synthetic, Electrochemical, Optical, and Conductivity Studies of Coordination Polymers of Iron, Ruthenium, and Osmium Octaethylporphyrin", J. Am. Chem. Soc., 109: 4606-4614, 1987.22Communication Pursuant to Article 94(3) EPC Dated Mar. 18, 2010 From the European Patent Office Re.: Application No. 03741037.0.23Communication Pursuant to Article 96(2) EPC Dated Jul. 10, 2006 From the European Patent Office Re.: Application No. 02725096.8.24Cotton et al. "Supramolecular Arrays Based on Dimetal Building Units", Accounts of Chemical Research, 34(10): 759-771, 2001.25Davis "Synthetic Molecular Motors", Nature, 401: 120-121, 1999.26Examiner Report Dated Jun. 24, 2008 From the Australian Government Re.: Application No. 2003281730.27Feringa "In Control of Molecular Motion", Nature, 408: 151-154, 2000.28Feringa "In Control of Motion: From Molecular Switches to Molecular Motors", Acc. Chem. Res., 34(6): 504-513, 2001.29Funatsu et al. "Perpendicularly Arranged Ruthenium Porphyrin Dimers and Trimers", Inorg. Chem., 36: 1625-1635, 1997.30Gomez-Lopes et al. "The Art and Science of Self-Assembling Molecular Machines", Nanotechnology, 7: 183-192, 1996.31Grund et al. "Resonant Nonlinear Optical Properties of Spin-Cast Films of Soluble Oligomeric Bridged (Phthalocyaninato) Ruthenium(II) Complexes", J. Phys. Chem., 96: 7450-7454, 1992.32Hanack et al. "Synthesis and Properties of Conducting Bridged Macrocyclic Metal Complexes" Institut fuer Organische Chemie, Universitaet Tuebingen, Germany, p. 126, 1997.33Hannak et al. "An Organometallic B12-Rotaxane and a B12-Dimer, Relaxed and Loaded Forms of a 'Molecular Spring", J. Am. Chem. Soc., 119: 2313-2314, 1997.34Hannak et al. "An Organometallic B12-Rotaxane and a B12-Dimer, Relaxed and Loaded Forms of a ′Molecular Spring", J. Am. Chem. Soc., 119: 2313-2314, 1997.35Hirsch et al. "Bridged Mixed Valence Phthalocyaninato-Metal Compounds", Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, p. 163-169, 1990.36International Preliminary Examination Report Dated Apr. 15, 2004 From the International Preliminary Examining Authority Re.: Application No. PCT/IL03/00612.37International Preliminary Examination Report Dated Jun. 19, 2003 From the International Preliminary Examining Authority Re.: Application No. PCT/US02/07178.38International Search Report Dated Jan. 30, 2004 From the International Searching Authority Re.: Application No. PCT/IL03/00612.39Jimenez et al. "Towards Synthetic Molecular Muscles: Contaction and Streching of a Linear Rotaxane Dimer", Angew. Chem. Int. Ed., 39(18): 3284-3287, 2000.40Joachim et al. "An Electrochemical Amplifier Using a Single Molecule", Chemical Physics Letters, 265: 353-357, 1997.41Kahn, Olivier "Chemistry and Physics of Molecular-Based Polymers Exhibiting A Spontaneous Magnetization", Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, p. 247-261, 1990.42Kelly "Progress Toward a Rationally Designed Molecular Motor", Acc. Chem. Res., 34: 514-522, 2001.43Kim et al. "Synthesis, Structure, and Modeling of a Cyclic Rhodium(III) Porphyrin Dimer With an Encapsulated 4,4-Bipyridine Ligand", Inorg. Chem., 38: 5178-5183, 1999.44Kobel et al. "Bisaxially Coordinated (Phthalocyaninato) Ruthenium(II) Compounds", Inorg. Chem., 25: 103-107, 1986.45Kurzweil "The Drexler-Smalley Debate on Molecular Assembly", Kurzweilai.net, p. 1-15, 2003.46Leigh et al. "A Quantum-Mechanical Description of Macrocyclic Ring Rotation in Benzylic Amide[2]Catenanes", Chem. Eur. J., 7(7): 1450-1454, 2001.47Lui et al. "Switchable Molecular Devices: From Rotaxanes to Nanoparticles", Structure and Bonding, 99: 141-145, 2001.48Mahadevan et al. "Motility Powered by Supramolecular Springs and Rachets", Science, 288: 95-99, 2000.49Merkle "Molecular Building Blocks and Development Strategies for Molecular Nanotechnology", Nanotechnology, 11: 89-99, 2000.50Nagata et al. "Synthesis and Optical Properties of Conformationally Constrained Trimeric and Pentameric Porphyrin Arrays", J. Am. Chem. Soc., 112: 3054-3059, 1990.51Nakash et al. "Product-Induced Distortion of a Metalloporphyrin Host: Implications for Acceleration of Diels-Alder Reactions", J. Am. Chem. Soc., 122: 5286-5293, 2000.52Nakash et al. "Structure-Activity Relationships in the Acceleration of a Hetero Diels-Alder Reaction by Metalloporphyrin Hosts", J. Org. Chem., 65: 7266-7271, 2000.53Noy et al. "Optical Absorption and Computational Studies of [Ni]-Bacteriochlorophyll-alpha. New Insight Into Charge Distribution Between Metal and Ligands", J. Am. Chem. Soc., 122: 3937-3944, 2000.54Noy et al. "Optical Absorption and Computational Studies of [Ni]-Bacteriochlorophyll-α. New Insight Into Charge Distribution Between Metal and Ligands", J. Am. Chem. Soc., 122: 3937-3944, 2000.55Office Action Dated Feb. 22, 2009 From the Israeli Patent Office Re.: Application No. 166566 and Its Translation Into English.56Official Action Dated Aug. 24, 2007 From the US Patent and Trademark Office Re.: U.S. Appl. No. 10/207,860.57Official Action Dated Jul. 10, 2006 From the US Patent and Trademark Office Re.: U.S. Appl. No. 10/207,860.58Official Action Dated Mar. 7, 2007 From the US Patent and Trademark Office Re.: U.S. Appl. No. 10/207,860.59Official Action Dated Oct. 28, 2009 From the US Patent and Trademark Office Re.: U.S. Appl. No. 12/071,710.60Otero et al. "Soft and Wet Conducting Polymers for Artificial Muscles", Adv. Mater., 10(6): 491-494, 1998.61Pease et al. "Computing at the Molecular Level", Structure & Bonding, 99: 224-227, 2001.62Response Dated Mar. 15, 2010 to Official Action Dated Dec. 15, 2009 From the US Patent and Trademark Office Re.: U.S. Appl. No. 10/468,840.63Response Dated Mar. 29, 2010 to Official Action of Oct. 28, 2009 From the US Patent and Trademark Office Re.: U.S. Appl. No. 12/071,710.64Schneider et al. "Phthalocyaninatoeisen mit Pyrazin als zweizaehnigem Brueckenliganden", Angew. Chem., 92(5): 391-393, 1980.65Seki et al. "Photoresponsive Monolayers on Water and Solid Surfaces", Supramolecular Science, 5(3-4): 373-377, 1998.66Supplementary European Search Report Dated Jul. 13, 2005 From the European Patent Office Re.: Application No. 02725096.8.67Tanaka et al. "Clathrate Formation by and Self-Assembled Supramolecular Structures of a 'Molecular Spring'", Chem. Soc., Perkin Trans., 2: 2492-2497, 2000.68Tanaka et al. "Clathrate Formation by and Self-Assembled Supramolecular Structures of a ‘Molecular Spring’", Chem. Soc., Perkin Trans., 2: 2492-2497, 2000.69Tashiro et al. "A Cyclinc Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex With C60", J. Am. Chem. Soc., 121: 9477-9478, 1999.70Tashiro et al. "Metal Bisporphyrinate Double-Decker Complexes as Redox-Responsive Rotating Modules. Studies in Ligand Rotation Activities of the Reduced and Oxidized Forms Using Chirality as a Probe", J. Am. Chem. Soc., 122: 7921-7926, 2000.71Taylor et al. "Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders", J. Am. Chem. Soc., 121: 11538-11545, 1999.72Translation of Notice of Reason for Rejection Dated Dec. 5, 2008 From the Japanese Patent Office Re.: Application No. 2004-524034.73Tuzun et al. "Dynamics of A Laser Driven Molecular Motor", Nanotechnology, 6: 52-63, 1995.74Venturi et al. "Electrochemistry of Coordination Compounds: An Extended View", Coordination Chemistry Reviews, 185-186: 233-256, 1999.75Willner "Layered Molecular Optoelectronic Assemblies", J. Mater. Chem., 8: 2543-2556, 1998.Classifications U.S. Classification365/151, 365/106, 365/173, 365/153, 540/145International ClassificationG11C13/00, C07B47/00, F16F1/36, C07K14/00, B82B1/00, F16F3/00, F03G7/00, F16F1/00, C07D487/22Cooperative ClassificationF16F3/00, F16F1/00, F16F1/3605European ClassificationF16F1/36B, F16F1/00, F16F3/00Legal EventsDateCodeEventDescriptionSep 3, 2003ASAssignmentOwner name: YEDA RESEARCH AND DEVELOPMENT CO. LTD., ISRAELFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:YERUSHALMI, ROIE;SCHERZ, AVIGDOR;REEL/FRAME:014938/0075Effective date: 20030730Jun 20, 2014REMIMaintenance fee reminder mailedNov 9, 2014LAPSLapse for failure to pay maintenance feesDec 30, 2014FPExpired due to failure to pay maintenance feeEffective date: 20141109RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services