메뉴 건너뛰기




Volumn 2, Issue 1, 2008, Pages 97-106

Synthesis and photoisomerization of fullerene- and oligo(phenylene ethynylene) - Azobenzene derivatives

Author keywords

Azobenzene; Fullerene; Molecular machines; Nanomachines; OPE; Photoisomerization

Indexed keywords

AZOBENZENE; ENERGY TRANSFER; FUNCTIONAL GROUPS; PHOTOISOMERIZATION;

EID: 42549106561     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn700294m     Document Type: Article
Times cited : (48)

References (54)
  • 3
    • 0003822943 scopus 로고    scopus 로고
    • AIP Press/Springer: New York
    • Timp, G. L. Nanotechnology; AIP Press/Springer: New York, 1999.
    • (1999) Nanotechnology
    • Timp, G.L.1
  • 4
    • 0034735798 scopus 로고    scopus 로고
    • Electronics Using Hybrid-Molecular and Mono-Molecular Devices
    • Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-Molecular Devices. Nature 2000, 408, 541-548.
    • (2000) Nature , vol.408 , pp. 541-548
    • Joachim, C.1    Gimzewski, J.K.2    Aviram, A.3
  • 5
    • 2342486652 scopus 로고    scopus 로고
    • The Path to Ubiquitous and Low-Cost Organic Electronic Appliances on Plastic
    • Forrest, S. R. The Path to Ubiquitous and Low-Cost Organic Electronic Appliances on Plastic. Nature 2004, 428, 911-918.
    • (2004) Nature , vol.428 , pp. 911-918
    • Forrest, S.R.1
  • 7
    • 33846152351 scopus 로고    scopus 로고
    • Synthetic Molecular Motors and Mechanical Machines
    • Kay, E. R.; Leigh, D. A.; Zerbetto, F. Synthetic Molecular Motors and Mechanical Machines. Angew. Chem. Int. Ed. 2007, 46, 72-191.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 72-191
    • Kay, E.R.1    Leigh, D.A.2    Zerbetto, F.3
  • 8
    • 0342955086 scopus 로고    scopus 로고
    • Atomic Scale Engines: Cars and Wheels
    • Porto, M.; Urbakh, M.; Klafter, J. Atomic Scale Engines: Cars and Wheels. Phys. Rev. Lett. 2000, 84, 6058-6061.
    • (2000) Phys. Rev. Lett , vol.84 , pp. 6058-6061
    • Porto, M.1    Urbakh, M.2    Klafter, J.3
  • 12
    • 0003520820 scopus 로고    scopus 로고
    • Shibaski, M, Stoddart J. F, Vogtle F, Eds, Wiley-VCH: Weinheim, Germany
    • Stimulating Concepts in Chemistry; Shibaski, M,, Stoddart J. F., Vogtle F., Eds.; Wiley-VCH: Weinheim, Germany, 2000.
    • (2000) Stimulating Concepts in Chemistry
  • 13
    • 17444412718 scopus 로고    scopus 로고
    • Electron and Energy Transfer Modulation with Photochromic Switches
    • Raymo, F. M.; Tomasulo, M. Electron and Energy Transfer Modulation with Photochromic Switches. Chem. Soc. Rev. 2005, 34, 327-336.
    • (2005) Chem. Soc. Rev , vol.34 , pp. 327-336
    • Raymo, F.M.1    Tomasulo, M.2
  • 14
    • 23644459048 scopus 로고    scopus 로고
    • Elucidating Excited State Electronic Structure and Intercomponent Interactions in Multicomponent and Supramolecular Systems
    • Browne, W. R.; O'Boyle, N. M.; McGarvey, J. J.; Vos, J. G. Elucidating Excited State Electronic Structure and Intercomponent Interactions in Multicomponent and Supramolecular Systems. Chem. Soc. Rev. 2005, 34, 641-663.
    • (2005) Chem. Soc. Rev , vol.34 , pp. 641-663
    • Browne, W.R.1    O'Boyle, N.M.2    McGarvey, J.J.3    Vos, J.G.4
  • 15
    • 33646463427 scopus 로고    scopus 로고
    • En Route to a Motorized Nanocar
    • Morin, J.; Shirai, Y.; Tour, J. M. En Route to a Motorized Nanocar. Org. Lett. 2006, 8, 1713-1716.
    • (2006) Org. Lett , vol.8 , pp. 1713-1716
    • Morin, J.1    Shirai, Y.2    Tour, J.M.3
  • 16
    • 0037591382 scopus 로고    scopus 로고
    • Schuster, D. I.; Nuber, B.; Vail, S. A.; ManMahon, S.; Lin, C,; Wilson, S. R.; Khong, A. Synthesis, Photochemistry and Photophysics of Stilbene-Derivatized Fullerenes. Photochem. Photobiol. Sci. 2003, 2, 315-321.
    • Schuster, D. I.; Nuber, B.; Vail, S. A.; ManMahon, S.; Lin, C,; Wilson, S. R.; Khong, A. Synthesis, Photochemistry and Photophysics of Stilbene-Derivatized Fullerenes. Photochem. Photobiol. Sci. 2003, 2, 315-321.
  • 17
    • 85044354091 scopus 로고
    • The cis-Form of Azobenzene
    • Hartley, G. S. The cis-Form of Azobenzene. Nature 1937, 140, 281-282.
    • (1937) Nature , vol.140 , pp. 281-282
    • Hartley, G.S.1
  • 19
    • 17044444652 scopus 로고    scopus 로고
    • Directed Bending of a Polymer Film by Light
    • Yu, Y.; Nakano, M.; Ikeda, T. Directed Bending of a Polymer Film by Light. Nature 2003, 425, 145-156.
    • (2003) Nature , vol.425 , pp. 145-156
    • Yu, Y.1    Nakano, M.2    Ikeda, T.3
  • 20
    • 0347063849 scopus 로고    scopus 로고
    • Phase Switching of a Single Isomeric Molecule and Associated Characteristic Rectification
    • Yasuda, S.; Nakamura, T.; Matsumoto, M.; Shigekawa, H. Phase Switching of a Single Isomeric Molecule and Associated Characteristic Rectification. J. Am. Chem. Soc. 2003, 125, 16430-16433.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 16430-16433
    • Yasuda, S.1    Nakamura, T.2    Matsumoto, M.3    Shigekawa, H.4
  • 21
    • 0034595660 scopus 로고    scopus 로고
    • Ichimura, K.; Oh, S.-K; Nakagawa, M. Light-Driven Motion of Liquids on a Photoresponsive Surface. Science 2000, 288, 1624-1626.
    • Ichimura, K.; Oh, S.-K; Nakagawa, M. Light-Driven Motion of Liquids on a Photoresponsive Surface. Science 2000, 288, 1624-1626.
  • 23
    • 0001223050 scopus 로고    scopus 로고
    • Fullerene Materials
    • Prato, M. Fullerene Materials. Top. Curr. Chem. 1999, 199, 173-187.
    • (1999) Top. Curr. Chem , vol.199 , pp. 173-187
    • Prato, M.1
  • 24
    • 18144388306 scopus 로고    scopus 로고
    • Supramolecular Design of Photocurrent-Generating Devices Using Fullerenes Aimed at Modelling Artificial Photosynthesis
    • Konishi, T.; Ikeda, A.; Shinkai, S. Supramolecular Design of Photocurrent-Generating Devices Using Fullerenes Aimed at Modelling Artificial Photosynthesis. Tetrahedron 2005, 61, 4881-4899.
    • (2005) Tetrahedron , vol.61 , pp. 4881-4899
    • Konishi, T.1    Ikeda, A.2    Shinkai, S.3
  • 26
    • 0033750821 scopus 로고    scopus 로고
    • aryleneethynylenes: Syntheses, Properties, Structures, and Applications
    • Bunz, U. H. F. Poly(aryleneethynylene)s: Syntheses, Properties, Structures, and Applications. Chem. Rev. 2000, 100, 1605-1644.
    • (2000) Chem. Rev , vol.100 , pp. 1605-1644
    • Bunz, U.H.F.P.1
  • 27
    • 0347359146 scopus 로고    scopus 로고
    • Molecular Rods. 1. Simple Axial Rods
    • Schwab, P. F. H.; Levin, M. D.; Michl, J. Molecular Rods. 1. Simple Axial Rods. Chem. Rev. 1999, 99, 1863-1933.
    • (1999) Chem. Rev , vol.99 , pp. 1863-1933
    • Schwab, P.F.H.1    Levin, M.D.2    Michl, J.3
  • 28
    • 28144452507 scopus 로고    scopus 로고
    • Directional Control in Thermally Driven Single-Molecule Nanocars
    • Shirai, Y.; Osgood, A. J.; Zhao, Y.; Kelly, K. F.; Tour, J. M. Directional Control in Thermally Driven Single-Molecule Nanocars. Nano Lett. 2005, 5, 2330-2334.
    • (2005) Nano Lett , vol.5 , pp. 2330-2334
    • Shirai, Y.1    Osgood, A.J.2    Zhao, Y.3    Kelly, K.F.4    Tour, J.M.5
  • 31
    • 1242297021 scopus 로고    scopus 로고
    • Photoswitchable Flexible and Shape-Persistent Dendrimers: Comparison of the Interplay between a Photochromic Azobenzene Core and Dendrimer Structure
    • Liao, L.-X.; Stellacci, F.; McGrath, D. V. Photoswitchable Flexible and Shape-Persistent Dendrimers: Comparison of the Interplay between a Photochromic Azobenzene Core and Dendrimer Structure. J. Am. Chem. Soc. 2004, 126, 2181-2185.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 2181-2185
    • Liao, L.-X.1    Stellacci, F.2    McGrath, D.V.3
  • 32
    • 0141594835 scopus 로고    scopus 로고
    • Synthesis and Testing of New End-Functionalized Oligomers for Molecular Electronics
    • Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A.; Tour, J. M. Synthesis and Testing of New End-Functionalized Oligomers for Molecular Electronics. Tetrahedron 2003, 59, 8555-8570.
    • (2003) Tetrahedron , vol.59 , pp. 8555-8570
    • Flatt, A.K.1    Dirk, S.M.2    Henderson, J.C.3    Shen, D.E.4    Su, J.5    Reed, M.A.6    Tour, J.M.7
  • 33
    • 33748706349 scopus 로고    scopus 로고
    • Syntheses of New Functionalized Azobenzenes for Potential Molecular Electronic Devices
    • Yu, B.-C.; Shirai, Y.; Tour, J. M. Syntheses of New Functionalized Azobenzenes for Potential Molecular Electronic Devices. Tetrahedron 2006, 62, 10303-10310.
    • (2006) Tetrahedron , vol.62 , pp. 10303-10310
    • Yu, B.-C.1    Shirai, Y.2    Tour, J.M.3
  • 34
    • 3142713774 scopus 로고    scopus 로고
    • Facile Synthesis of Multifullerene-OPE Hybrids via in Situ Ethynylation
    • Shirai, Y.; Zhao, Y.; Cheng, L.; Tour, J. M. Facile Synthesis of Multifullerene-OPE Hybrids via in Situ Ethynylation. Org. Lett. 2004, 6, 2129-2132.
    • (2004) Org. Lett , vol.6 , pp. 2129-2132
    • Shirai, Y.1    Zhao, Y.2    Cheng, L.3    Tour, J.M.4
  • 35
    • 0041645454 scopus 로고
    • Solvent-induced Conformational Changes of Arylazo-Substituted Polyaspartates
    • Ueno, A.; Takahashi, K.; Anzai, J.-I.; Osa, T. Solvent-induced Conformational Changes of Arylazo-Substituted Polyaspartates. Bull. Chem. Soc. Jpn. 1980, 53, 1988-1992.
    • (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1988-1992
    • Ueno, A.1    Takahashi, K.2    Anzai, J.-I.3    Osa, T.4
  • 36
    • 20644467266 scopus 로고    scopus 로고
    • Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene-oligo(p-phenylene ethynylene) Hybrids
    • Zhao, Y.; Shirai, Y.; Slepkov, A. D.; Cheng, L.; Alemany, L. B.; Sasaki, T.; Hegmann, F. A.; Tour, J. M. Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene-oligo(p-phenylene ethynylene) Hybrids. Chem. - Eur. J. 2005, 11, 3643-3658.
    • (2005) Chem. - Eur. J , vol.11 , pp. 3643-3658
    • Zhao, Y.1    Shirai, Y.2    Slepkov, A.D.3    Cheng, L.4    Alemany, L.B.5    Sasaki, T.6    Hegmann, F.A.7    Tour, J.M.8
  • 38
    • 84989539773 scopus 로고
    • One Pot Synthesis of Haloacetylenes from Trimethylsilylacetylenes
    • Nishikawa, T.; Shibuya, S.; Hosokawa, S.; Isobe, M. One Pot Synthesis of Haloacetylenes from Trimethylsilylacetylenes. Synlett 1994, 485-486.
    • (1994) Synlett , pp. 485-486
    • Nishikawa, T.1    Shibuya, S.2    Hosokawa, S.3    Isobe, M.4
  • 39
    • 6444238094 scopus 로고    scopus 로고
    • A New, Iterative Strategy for the Synthesis of Unsymmetrical Polyynes: Application to the Total Synthesis of 15,16-Dihydrominquartynoic Acid
    • Kim, S.; Kim, S.; Lee, T.; Ko, H.; Kim, D. A New, Iterative Strategy for the Synthesis of Unsymmetrical Polyynes: Application to the Total Synthesis of 15,16-Dihydrominquartynoic Acid. Org. Lett. 2004, 6, 3601-3604.
    • (2004) Org. Lett , vol.6 , pp. 3601-3604
    • Kim, S.1    Kim, S.2    Lee, T.3    Ko, H.4    Kim, D.5
  • 41
    • 84982336370 scopus 로고
    • Über den Mechanismus der Katalytischen cis-trans Umlagerung von Azobenzol.
    • Schulte-Frohlinde, D. Über den Mechanismus der Katalytischen cis-trans Umlagerung von Azobenzol. Justus Liebigs Ann. Chem. 1958, 612, 131-138.
    • (1958) Justus Liebigs Ann. Chem , vol.612 , pp. 131-138
    • Schulte-Frohlinde, D.1
  • 42
    • 0038128851 scopus 로고    scopus 로고
    • Guldi, D. M, Martin, N, Eds, Kluwer Academic Publishers: Dordrecht, The Netherlands
    • Fullerenes: From Synthesis to Optoelectronic Properties; Guldi, D. M., Martin, N., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002.
    • (2002) Fullerenes: From Synthesis to Optoelectronic Properties
  • 44
    • 0034640042 scopus 로고    scopus 로고
    • Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials
    • and references therein
    • Åstrand, P.-O.; Ramanujam, P. S.; Hvilsted, S.; Bak, K. L.; Sauer, S. P. A. Ab Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials. J. Am. Chem. Soc. 2000, 122, 3482-3487, and references therein.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 3482-3487
    • Åstrand, P.-O.1    Ramanujam, P.S.2    Hvilsted, S.3    Bak, K.L.4    Sauer, S.P.A.A.5
  • 45
    • 33947311546 scopus 로고
    • Photosensitized Isomerization of Azobenzene
    • Fischer, E. Photosensitized Isomerization of Azobenzene. J. Am. Chem. Soc. 1968, 90, 796-797.
    • (1968) J. Am. Chem. Soc , vol.90 , pp. 796-797
    • Fischer, E.1
  • 46
    • 8544229082 scopus 로고    scopus 로고
    • Synthesis and Photochemical Properties of Porphyrin-Azobenzene Triad
    • Yamamura, T.; Momotake, A.; Arai, T. Synthesis and Photochemical Properties of Porphyrin-Azobenzene Triad. Tetrahedron. Lett. 2004, 45, 9219-9223.
    • (2004) Tetrahedron. Lett , vol.45 , pp. 9219-9223
    • Yamamura, T.1    Momotake, A.2    Arai, T.3
  • 47
    • 1642414058 scopus 로고
    • Mechanisms of Photochemical Reactions in Solution. XXX. Photosensitized Isomerization of Azobenzene
    • Jones, L. B.; Hammond, G. S. Mechanisms of Photochemical Reactions in Solution. XXX. Photosensitized Isomerization of Azobenzene. J. Am. Chem. Soc. 1965, 87, 4219-4220.
    • (1965) J. Am. Chem. Soc , vol.87 , pp. 4219-4220
    • Jones, L.B.1    Hammond, G.S.2
  • 48
    • 0000217427 scopus 로고
    • Cis-Trans Photoisomerization of Azobenzene. Solvent and Triplet Donor Effects
    • Bortolus, P.; Monti, S. Cis-Trans Photoisomerization of Azobenzene. Solvent and Triplet Donor Effects. J. Phys. Chem. 1979, 83, 648-652.
    • (1979) J. Phys. Chem , vol.83 , pp. 648-652
    • Bortolus, P.1    Monti, S.2
  • 50
    • 42549090801 scopus 로고    scopus 로고
    • max ≈ 330-400 nm) reflects the minimum concentration of cis isomer at the photostationary state; see refs 51 and 52.
    • max ≈ 330-400 nm) reflects the minimum concentration of cis isomer at the photostationary state; see refs 51 and 52.
  • 51
    • 0001597754 scopus 로고    scopus 로고
    • Effect of Media Polarity on the Photoisomerisation of Substituted Stilbene, Azobenzene and Imine Chromophores
    • King, N. R.; Whale, E. A.; Davis, F. J.; Gilbert, A., Mitchell, G. R. Effect of Media Polarity on the Photoisomerisation of Substituted Stilbene, Azobenzene and Imine Chromophores. J. Mater. Chem. 1997, 7, 625-630.
    • (1997) J. Mater. Chem , vol.7 , pp. 625-630
    • King, N.R.1    Whale, E.A.2    Davis, F.J.3    Gilbert, A.4    Mitchell, G.R.5
  • 52
    • 0001667414 scopus 로고    scopus 로고
    • Brode, W. R.; Gould, J. H.; Wyman, G. M. The Relation between the Absorption Spectra and the Chemical Constitution of Dyes. XXV. Phototropism and cis-trans Isomerism in Aromatic Azo Compounds. J. Am. Chem. Soc. 1952, 74, 4641-4646.
    • Brode, W. R.; Gould, J. H.; Wyman, G. M. The Relation between the Absorption Spectra and the Chemical Constitution of Dyes. XXV. Phototropism and cis-trans Isomerism in Aromatic Azo Compounds. J. Am. Chem. Soc. 1952, 74, 4641-4646.
  • 53
    • 0033583143 scopus 로고    scopus 로고
    • Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers
    • Yu, C. J.; Chong, Y.; Kayyem, J. F.; Gozin, M. Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers. J. Org. Chem. 1999, 64, 2070-2079.
    • (1999) J. Org. Chem , vol.64 , pp. 2070-2079
    • Yu, C.J.1    Chong, Y.2    Kayyem, J.F.3    Gozin, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.