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Volumn 214, Issue 2-3, 2010, Pages 121-127

Theoretical study on photochemical behavior of trans-2-[4′- (dimethylamino)styryl]benzothiazole

Author keywords

Photoisomerization; Photophysics; Push pull aromatic olefin; TDDFT; TICT

Indexed keywords


EID: 77956056517     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.06.014     Document Type: Article
Times cited : (12)

References (47)
  • 2
    • 0040232920 scopus 로고
    • Photoisomerization dynamics of stilbenes
    • D.H. Waldeck Photoisomerization dynamics of stilbenes Chem. Rev. 91 1991 415 436
    • (1991) Chem. Rev. , vol.91 , pp. 415-436
    • Waldeck, D.H.1
  • 4
    • 41749120999 scopus 로고    scopus 로고
    • Photoisomerization of the green fluorescence protein chromophore and the meta- and para-amino analogues
    • J.-S. Yang, G.-J. Huang, Y.-H. Liu, and S.-M. Peng Photoisomerization of the green fluorescence protein chromophore and the meta- and para-amino analogues Chem. Commun. 2008 1344 1346
    • (2008) Chem. Commun. , pp. 1344-1346
    • Yang, J.-S.1    Huang, G.-J.2    Liu, Y.-H.3    Peng, S.-M.4
  • 5
    • 0042706825 scopus 로고    scopus 로고
    • Cis-trans isomerization of organic molecules and biomolecules: Implications and applications
    • C. Dugave, and L. Demange Cis-trans isomerization of organic molecules and biomolecules: implications and applications Chem. Rev. 103 2003 2475 2532
    • (2003) Chem. Rev. , vol.103 , pp. 2475-2532
    • Dugave, C.1    Demange, L.2
  • 6
    • 0030605457 scopus 로고    scopus 로고
    • Nonradiative twisted intramolecular charge transfer state in polar stilbenes: Photophysical study of 4-perfluorooctylsulfonyl-4′-N,N- dimethylamino stilbene and two bridged derivatives
    • H. Le Breton, B. Bennetau, J.-F. Letard, R. Lapouyade, and W. Rettig Nonradiative twisted intramolecular charge transfer state in polar stilbenes: photophysical study of 4-perfluorooctylsulfonyl-4′-N,N-dimethylamino stilbene and two bridged derivatives J. Photochem. Photobiol. A: Chem. 95 1996 7 20
    • (1996) J. Photochem. Photobiol. A: Chem. , vol.95 , pp. 7-20
    • Le Breton, H.1    Bennetau, B.2    Letard, J.-F.3    Lapouyade, R.4    Rettig, W.5
  • 7
    • 34047229934 scopus 로고    scopus 로고
    • Charge-transfer transitions in twisted stilbenoids: Interchangeable features and generic distinctions of single- and double-bond twists
    • M. Dekhtyar, and W. Rettig Charge-transfer transitions in twisted stilbenoids: interchangeable features and generic distinctions of single- and double-bond twists J. Phys. Chem. A 111 2007 2035 2039
    • (2007) J. Phys. Chem. A , vol.111 , pp. 2035-2039
    • Dekhtyar, M.1    Rettig, W.2
  • 9
    • 0003056557 scopus 로고    scopus 로고
    • Photochemistry and photophysics of donor-acceptor-polyenes. I: All-trans-4-dimethylamino-4′-cyano-1,4-diphenylbutadiene (DCB)
    • H. Braatz, S. Hecht, H. Seifert, S. Helm, J. Bendig, and W. Rettig Photochemistry and photophysics of donor-acceptor-polyenes. I: all-trans-4-dimethylamino-4′-cyano-1,4-diphenylbutadiene (DCB) J. Photochem. Photobiol. A: Chem. 123 1999 99 108
    • (1999) J. Photochem. Photobiol. A: Chem. , vol.123 , pp. 99-108
    • Braatz, H.1    Hecht, S.2    Seifert, H.3    Helm, S.4    Bendig, J.5    Rettig, W.6
  • 10
    • 0034528384 scopus 로고    scopus 로고
    • Two-photon pumped lasing stilbene-type chromophores containing various terminal donor groups: Relationship between lasing efficiency and intramolecular charge transfer
    • X.-M. Wang, Y.-F. Zhou, W.-T. Yu, C. Wang, Q. Fang, M.-H. Jiang, H. Leib, and H.-Z. Wang Two-photon pumped lasing stilbene-type chromophores containing various terminal donor groups: relationship between lasing efficiency and intramolecular charge transfer J. Mater. Chem. 10 2000 2698 2703
    • (2000) J. Mater. Chem. , vol.10 , pp. 2698-2703
    • Wang, X.-M.1    Zhou, Y.-F.2    Yu, W.-T.3    Wang, C.4    Fang, Q.5    Jiang, M.-H.6    Leib, H.7    Wang, H.-Z.8
  • 11
    • 4644277919 scopus 로고    scopus 로고
    • Substituent-dependent photoinduced intramolecular charge transfer in N-aryl-substituted trans-4-aminostilbenes
    • J.-S. Yang, K.-L. Liau, C.-M. Wang, and C.-Y. Hwang Substituent-dependent photoinduced intramolecular charge transfer in N-aryl-substituted trans-4-aminostilbenes J. Am. Chem. Soc. 126 2004 12325 12335
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12325-12335
    • Yang, J.-S.1    Liau, K.-L.2    Wang, C.-M.3    Hwang, C.-Y.4
  • 12
    • 0035894952 scopus 로고    scopus 로고
    • Ab initio study on the photochemical behavior of 4-dimethylamino, 4′-cyanostilbene
    • Y. Amatatsu Ab initio study on the photochemical behavior of 4-dimethylamino, 4′-cyanostilbene Chem. Phys. 274 2001 87 98
    • (2001) Chem. Phys. , vol.274 , pp. 87-98
    • Amatatsu, Y.1
  • 13
    • 0141841689 scopus 로고    scopus 로고
    • Protonation dependent photoinduced intramolecular charge transfer in 2-(p-dimethylaminostyryl)benzazoles
    • T.A. Fayed, and S.S. Ali Protonation dependent photoinduced intramolecular charge transfer in 2-(p-dimethylaminostyryl)benzazoles Spectrosc. Lett. 36 2003 375 386
    • (2003) Spectrosc. Lett. , vol.36 , pp. 375-386
    • Fayed, T.A.1    Ali, S.S.2
  • 14
    • 56349171596 scopus 로고    scopus 로고
    • Excited state isomerization and effect of viscosity- and temperature-dependent torsional relaxation on TICT fluorescence of trans-2-[4-(dimethylamino)styryl]benzothiazole
    • S.K. Saha, P. Purkayastha, and A.B. Das Excited state isomerization and effect of viscosity- and temperature-dependent torsional relaxation on TICT fluorescence of trans-2-[4-(dimethylamino)styryl]benzothiazole J. Photochem. Photobiol. A: Chem. 199 2008 179 187
    • (2008) J. Photochem. Photobiol. A: Chem. , vol.199 , pp. 179-187
    • Saha, S.K.1    Purkayastha, P.2    Das, A.B.3
  • 15
    • 47749125342 scopus 로고    scopus 로고
    • Defining the different phases of premicellar aggregation using the photophysical changes of a surface-probing compound
    • S.S. Jaffer, M. Sowmiya, S.K. Saha, and P. Purkayastha Defining the different phases of premicellar aggregation using the photophysical changes of a surface-probing compound J. Colloids Interface Sci. 325 2008 236 242
    • (2008) J. Colloids Interface Sci. , vol.325 , pp. 236-242
    • Jaffer, S.S.1    Sowmiya, M.2    Saha, S.K.3    Purkayastha, P.4
  • 16
    • 49449092282 scopus 로고    scopus 로고
    • Intramolecular charge transfer probe induced formation of α-cyclodextrin nanotubular suprastructures: A concentration dependent process
    • S.S. Jaffer, S.K. Saha, G. Eranna, A.K. Sharma, and P. Purkayastha Intramolecular charge transfer probe induced formation of α-cyclodextrin nanotubular suprastructures: a concentration dependent process J. Phys. Chem. C 112 2008 11199 11204
    • (2008) J. Phys. Chem. C , vol.112 , pp. 11199-11204
    • Jaffer, S.S.1    Saha, S.K.2    Eranna, G.3    Sharma, A.K.4    Purkayastha, P.5
  • 17
    • 67649274263 scopus 로고    scopus 로고
    • Characterization of guest molecule concentration dependent nanotubes of β-cyclodextrin and their secondary assembly: Study with trans-2-[4-(dimethylamino)styryl]benzothiazole, a TICT-fluorescence probe
    • M. Sowmiya, P. Purkayastha, S.K. Saha, and S.S. Jaffer Characterization of guest molecule concentration dependent nanotubes of β-cyclodextrin and their secondary assembly: study with trans-2-[4-(dimethylamino)styryl] benzothiazole, a TICT-fluorescence probe J. Photochem. Photobiol. A: Chem. 205 2009 186 196
    • (2009) J. Photochem. Photobiol. A: Chem. , vol.205 , pp. 186-196
    • Sowmiya, M.1    Purkayastha, P.2    Saha, S.K.3    Jaffer, S.S.4
  • 18
    • 67649450460 scopus 로고    scopus 로고
    • Fragmentation of molecule-induced γ-cyclodextrin nanotubular suprastructures due to drug dosage
    • S.S. Jaffer, S.K. Saha, and P. Purkayastha Fragmentation of molecule-induced γ-cyclodextrin nanotubular suprastructures due to drug dosage J. Colloids Interface Sci. 337 2009 294 299
    • (2009) J. Colloids Interface Sci. , vol.337 , pp. 294-299
    • Jaffer, S.S.1    Saha, S.K.2    Purkayastha, P.3
  • 19
    • 46849119059 scopus 로고    scopus 로고
    • Photophysical characterization and effect of pH on the twisted intramolecular charge transfer fluorescence of trans-2-[4-(dimethylamino)styryl] benzothiazole
    • S.K. Saha, P. Purkayastha, and A.B. Das Photophysical characterization and effect of pH on the twisted intramolecular charge transfer fluorescence of trans-2-[4-(dimethylamino)styryl]benzothiazole J. Photochem. Photobiol. A: Chem. 195 2008 368 377
    • (2008) J. Photochem. Photobiol. A: Chem. , vol.195 , pp. 368-377
    • Saha, S.K.1    Purkayastha, P.2    Das, A.B.3
  • 20
    • 84985609328 scopus 로고
    • Charge separation in excited states of decoupled systems - TICT compounds and implications regarding the development of new laser dyes and the primary process of vision and photosynthesis
    • W. Rettig Charge separation in excited states of decoupled systems - TICT compounds and implications regarding the development of new laser dyes and the primary process of vision and photosynthesis Angew. Chem. Int. Ed. Engl. 25 1986 971 988
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 971-988
    • Rettig, W.1
  • 21
    • 0142231517 scopus 로고    scopus 로고
    • Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures
    • Z.R. Grabowski, K. Rotkiewicz, and W. Rettig Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem. Rev. 103 2003 3899 4302
    • (2003) Chem. Rev. , vol.103 , pp. 3899-4302
    • Grabowski, Z.R.1    Rotkiewicz, K.2    Rettig, W.3
  • 22
    • 0242594152 scopus 로고    scopus 로고
    • Excited-state intramolecular proton transfer (ESIPT) in 2-(2′-hydroxyphenyl)-oxazole and -thiazole
    • D. LeGourriérec, V. Kharlanov, R.G. Brown, and W. Rettig Excited-state intramolecular proton transfer (ESIPT) in 2-(2′- hydroxyphenyl)-oxazole and -thiazole J. Photochem. Photobiol. A: Chem. 130 2000 101 111
    • (2000) J. Photochem. Photobiol. A: Chem. , vol.130 , pp. 101-111
    • Legourriérec, D.1    Kharlanov, V.2    Brown, R.G.3    Rettig, W.4
  • 23
    • 44649171648 scopus 로고    scopus 로고
    • Study of intramolecular charge transfer of Michler's ketone using time dependent density functional theory
    • T. Pal, M. Paul, and S. Ghosh Study of intramolecular charge transfer of Michler's ketone using time dependent density functional theory J. Mol. Struct. (THEOCHEM) 860 2008 8 12
    • (2008) J. Mol. Struct. (THEOCHEM) , vol.860 , pp. 8-12
    • Pal, T.1    Paul, M.2    Ghosh, S.3
  • 24
    • 71049178713 scopus 로고    scopus 로고
    • Comparative theoretical study of rotamerism and excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)benzimidazole, 2-(2′-hydroxyphenyl)imidazo[4,5-b]pyridine, 2-(2′-hydroxyphenyl) imidazo[4,5-c]pyridine and 8-(2′-hydroxyphenyl)purine
    • F.A.S. Chipem, and G. Krishnamoorthy Comparative theoretical study of rotamerism and excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)benzimidazole, 2-(2′-hydroxyphenyl)imidazo[4,5- b]pyridine, 2-(2′-hydroxyphenyl)imidazo[4,5-c]pyridine and 8-(2′-hydroxyphenyl)purine J. Phys. Chem. A 113 2009 12063 12070
    • (2009) J. Phys. Chem. A , vol.113 , pp. 12063-12070
    • Chipem, F.A.S.1    Krishnamoorthy, G.2
  • 25
    • 10644250257 scopus 로고
    • Inhomogeneous electron gas
    • P. Hohenberg, and W. Kohn Inhomogeneous electron gas Phys. Rev. B 136 1964 864 871
    • (1964) Phys. Rev. B , vol.136 , pp. 864-871
    • Hohenberg, P.1    Kohn, W.2
  • 26
    • 0042113153 scopus 로고
    • Self-consistent equations including exchange and correlation effects
    • W. Kohn, and L. Sham Self-consistent equations including exchange and correlation effects J. Phys. Rev. A 140 1965 1133 1138
    • (1965) J. Phys. Rev. A , vol.140 , pp. 1133-1138
    • Kohn, W.1    Sham, L.2
  • 27
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • A.D. Becke Density-functional thermochemistry. 3. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 28
    • 0345491105 scopus 로고
    • Development of the Colle-Savetti correlation-energy formula into a functional of the electron-density
    • C. Lee, W. Yang, and R.G. Parr Development of the Colle-Savetti correlation-energy formula into a functional of the electron-density Phys. Rev. B 37 1988 785 789
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 29
    • 34250327185 scopus 로고    scopus 로고
    • Excited state intramolecular proton transfer in 2-(2′- arylsulfonamidophenyl)benzimidazole derivatives: Insights into the origin of donor substituent-induced emission energy shifts
    • Y. Wu, P.V. Lawson, M.M. Henary, K. Schmidt, J.-L. Brédas, and C.J. Fahrni Excited state intramolecular proton transfer in 2-(2′- arylsulfonamidophenyl)benzimidazole derivatives: insights into the origin of donor substituent-induced emission energy shifts J. Phys. Chem. A 111 2007 4584 4595
    • (2007) J. Phys. Chem. A , vol.111 , pp. 4584-4595
    • Wu, Y.1    Lawson, P.V.2    Henary, M.M.3    Schmidt, K.4    Brédas, J.-L.5    Fahrni, C.J.6
  • 30
    • 45149146260 scopus 로고
    • The CASSCF state interaction method
    • P.-A. Malmqvist, and B.O. Roos The CASSCF state interaction method Chem. Phys. Lett. 155 1989 189 194
    • (1989) Chem. Phys. Lett. , vol.155 , pp. 189-194
    • Malmqvist, P.-A.1    Roos, B.O.2
  • 31
    • 0037137775 scopus 로고    scopus 로고
    • Analytical gradients of a state average MCSCF state and a state average diagnostic
    • J. Stalring, A. Bernhardsson, and R. Lindh Analytical gradients of a state average MCSCF state and a state average diagnostic Mol. Phys. 99 2001 103 114
    • (2001) Mol. Phys. , vol.99 , pp. 103-114
    • Stalring, J.1    Bernhardsson, A.2    Lindh, R.3
  • 32
    • 1542347925 scopus 로고    scopus 로고
    • Theoretical study of benzotriazole UV photostability: Ultrafast deactivation through coupled proton and electron transfer triggered by a charge-transfer state
    • M.J. Paterson, M.A. Robb, L. Blancafort, and A.D. DeBellis Theoretical study of benzotriazole UV photostability: ultrafast deactivation through coupled proton and electron transfer triggered by a charge-transfer state J. Am. Chem. Soc. 126 2004 2912 2922
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2912-2922
    • Paterson, M.J.1    Robb, M.A.2    Blancafort, L.3    Debellis, A.D.4
  • 34
    • 0012753616 scopus 로고
    • A comparison of single reference methods for characterizing stationary points of excited state potential energy surfaces
    • J.F. Stanton, J. Gauss, N. Ishikawa, and M. Head-Gordon A comparison of single reference methods for characterizing stationary points of excited state potential energy surfaces J. Chem. Phys. 103 1995 4160 4174
    • (1995) J. Chem. Phys. , vol.103 , pp. 4160-4174
    • Stanton, J.F.1    Gauss, J.2    Ishikawa, N.3    Head-Gordon, M.4
  • 35
    • 0042151881 scopus 로고    scopus 로고
    • Theoretical study of the absorption and emission spectra of indole in the gas phase and in a solvent
    • L. Serrano-Andres, and B. Roos Theoretical study of the absorption and emission spectra of indole in the gas phase and in a solvent J. Am. Chem. Soc. 118 1996 185 195
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 185-195
    • Serrano-Andres, L.1    Roos, B.2
  • 36
    • 24944561009 scopus 로고    scopus 로고
    • Mechanism of an exceptional class of photostabilizers: A seam of conical intersection parallel to excited state intramolecular proton transfer (ESIPT) in o-hydroxyphenyl-(1,3,5)-triazine
    • M.J. Paterson, M.A. Robb, L. Blancafort, and A.D. DeBellis Mechanism of an exceptional class of photostabilizers: a seam of conical intersection parallel to excited state intramolecular proton transfer (ESIPT) in o-hydroxyphenyl-(1,3,5)-triazine J. Phys. Chem. A 109 2005 7527 7537
    • (2005) J. Phys. Chem. A , vol.109 , pp. 7527-7537
    • Paterson, M.J.1    Robb, M.A.2    Blancafort, L.3    Debellis, A.D.4
  • 38
    • 13444283674 scopus 로고    scopus 로고
    • Comparison of CIS- and EOM-CCSD-calculated adiabatic excited-state structures. Changes in charge density on going to adiabatic excited states
    • K.B. Wiberg, Y. Wang, A.E. de Oliveira, S.A. Perera, and P.H. Vaccaro Comparison of CIS- and EOM-CCSD-calculated adiabatic excited-state structures. Changes in charge density on going to adiabatic excited states J. Phys. Chem. A 109 2005 466 477
    • (2005) J. Phys. Chem. A , vol.109 , pp. 466-477
    • Wiberg, K.B.1    Wang, Y.2    De Oliveira, A.E.3    Perera, S.A.4    Vaccaro, P.H.5
  • 39
    • 0037034430 scopus 로고    scopus 로고
    • A comparative theoretical study on DMABN: Significance of excited state optimized geometries and direct comparison of methodologies
    • A.B.J. Parusel, W. Rettig, and W. Sudholt A comparative theoretical study on DMABN: significance of excited state optimized geometries and direct comparison of methodologies J. Phys. Chem. A 106 2002 804 815
    • (2002) J. Phys. Chem. A , vol.106 , pp. 804-815
    • Parusel, A.B.J.1    Rettig, W.2    Sudholt, W.3
  • 40
    • 73949091599 scopus 로고    scopus 로고
    • Role of intramolecular and intermolecular hydrogen bonding in both singlet and triplet excited states of aminofluorenones on internal conversion, intersystem crossing, and twisted intramolecular charge transfer
    • G.J. Zhao, and K.L. Han Role of intramolecular and intermolecular hydrogen bonding in both singlet and triplet excited states of aminofluorenones on internal conversion, intersystem crossing, and twisted intramolecular charge transfer J. Phys. Chem. A 113 2009 14329 14335
    • (2009) J. Phys. Chem. A , vol.113 , pp. 14329-14335
    • Zhao, G.J.1    Han, K.L.2
  • 41
    • 0001157659 scopus 로고
    • Time-dependent density functional response theory for molecules
    • M.E. Casida Time-dependent density functional response theory for molecules D.P. Chong, Recent Advances in Density Functional Methods Part I 1995 World Scientific Singapore 155 192
    • (1995) Recent Advances in Density Functional Methods Part i , pp. 155-192
    • Casida, M.E.1
  • 42
    • 0002301098 scopus 로고    scopus 로고
    • Density functional theory of time-dependent phenomena
    • E.K.U. Gross, J.F. Dobson, and M. Petersilka Density functional theory of time-dependent phenomena Top. Curr. Chem. 118 1996 81 172
    • (1996) Top. Curr. Chem. , vol.118 , pp. 81-172
    • Gross, E.K.U.1    Dobson, J.F.2    Petersilka, M.3
  • 47
    • 18744409064 scopus 로고    scopus 로고
    • Intramolecular charge transfer in 4-aminobenzonitriles does not necessarily need the twist
    • I. Gomez, M. Reguero, M. Boggio-Pasqua, and M.A. Robb Intramolecular charge transfer in 4-aminobenzonitriles does not necessarily need the twist J. Am. Chem. Soc. 127 2005 7119 7129
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 7119-7129
    • Gomez, I.1    Reguero, M.2    Boggio-Pasqua, M.3    Robb, M.A.4


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