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Volumn 17, Issue 4, 2012, Pages 4452-4459

Selective formation of twisted intramolecular charge transfer and excimer emissions on 2,7-bis(4-diethylaminophenyl)-fluorenone by choice of solvent

Author keywords

Donor acceptor dye; Excimer; Fluorenone; Intermolecular charge transfer; Twisted intramolecular charge transfer (TICT)

Indexed keywords

2,7 BIS(4 DIETHYLAMINOPHENYL) FLUORENONE; 2,7-BIS(4-DIETHYLAMINOPHENYL)-FLUORENONE; FLUORENE DERIVATIVE; FLUORESCENT DYE; SOLVENT;

EID: 84860261140     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17044452     Document Type: Article
Times cited : (28)

References (38)
  • 1
    • 0142231517 scopus 로고    scopus 로고
    • Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures
    • Grabowski, Z.R.; Rotkiewicz, K.; Rettig, W. Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures. Chem. Rev. 2003, 103, 3899-4032.
    • (2003) Chem. Rev. , vol.103 , pp. 3899-4032
    • Grabowski, Z.R.1    Rotkiewicz, K.2    Rettig, W.3
  • 2
    • 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
    • Rettig, W. 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. 1986, 25, 971-988.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 971-988
    • Rettig, W.1
  • 3
    • 0000611072 scopus 로고    scopus 로고
    • Effects of molecular structure and hydrogen bonding on the radiationless deactivation of singlet excited fluorenone derivatives
    • Biczók, L.; Bérces, T.; Inoue, H. Effects of molecular structure and hydrogen bonding on the radiationless deactivation of singlet excited fluorenone derivatives. J. Phys. Chem. A 1999, 103, 3837-3842.
    • (1999) J. Phys. Chem. A , vol.103 , pp. 3837-3842
    • Biczók, L.1    Bérces, T.2    Inoue, H.3
  • 4
    • 4243106516 scopus 로고
    • Environmental and magnetic field effects on exciplex and twisted charge transfer emission
    • Bhattacharyya, K.; Chowdhury, M. Environmental and magnetic field effects on exciplex and twisted charge transfer emission. Chem. Rev. 1993, 93, 507-535.
    • (1993) Chem. Rev. , vol.93 , pp. 507-535
    • Bhattacharyya, K.1    Chowdhury, M.2
  • 5
    • 0001407795 scopus 로고
    • Excited-state dipole moments of dual fluorescent 4-(dialkylamino) benzonitriles: Influence of alkyl chain length and effective solvent polarity
    • Schuddeboom, W.; Jonker, S.A.; Warman, J.M.; Leinhos, U.; Kuehnle, W.; Zachariasse, K.A. Excited-state dipole moments of dual fluorescent 4-(dialkylamino)benzonitriles: Influence of alkyl chain length and effective solvent polarity. J. Phys. Chem. 1992, 96, 10809-10819.
    • (1992) J. Phys. Chem. , vol.96 , pp. 10809-10819
    • Schuddeboom, W.1    Jonker, S.A.2    Warman, J.M.3    Leinhos, U.4    Kuehnle, W.5    Zachariasse, K.A.6
  • 6
    • 79953035149 scopus 로고    scopus 로고
    • Temperature dependence of the fluorescence properties of thioflavin-T in propanol, a glass-forming liquid
    • Amdursky, N.; Gepshtein, R.; Erez, Y.; Huppert, D. Temperature dependence of the fluorescence properties of thioflavin-T in propanol, a glass-forming liquid. J. Phys. Chem. A 2011, 115, 2540-2548.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 2540-2548
    • Amdursky, N.1    Gepshtein, R.2    Erez, Y.3    Huppert, D.4
  • 7
    • 79953052679 scopus 로고    scopus 로고
    • Heterogeneity in binary mixtures of (water + tertiary butanol): Temperature dependence across mixture composition
    • Gazi, H.A.R.; Biswas, R. Heterogeneity in binary mixtures of (water + tertiary butanol): Temperature dependence across mixture composition. J. Phys. Chem. A 2011, 115, 2447-2455.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 2447-2455
    • Gazi, H.A.R.1    Biswas, R.2
  • 9
    • 4544349097 scopus 로고    scopus 로고
    • Intramolecular charge transfer dual fluorescence of p- dimethylaminobenzoates
    • Zhang, C.H.; Chena, Z.B.; Jiang. Y.B. Intramolecular charge transfer dual fluorescence of p-dimethylaminobenzoates. Spectrochim. Acta A 2004, 60, 2729-2732.
    • (2004) Spectrochim. Acta A , vol.60 , pp. 2729-2732
    • Zhang, C.H.1    Chena, Z.B.2    Jiang, Y.B.3
  • 11
    • 70349784869 scopus 로고    scopus 로고
    • Metal-free organic dyes for dye-sensitized solar cells: From structure: Property relationships to design rules
    • Mishra, A.; Fischer, M.K.R.; Bäuerle, P. Metal-free organic dyes for dye-sensitized solar cells: From structure: Property relationships to design rules. Angew. Chem. Int. Ed. Engl. 2009, 48, 2474-2499.
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , pp. 2474-2499
    • Mishra, A.1    Fischer, M.K.R.2    Bäuerle, P.3
  • 12
    • 83455236801 scopus 로고    scopus 로고
    • [2.2] Paracyclophane as a bridging unit in the design of organic dyes for sensitized solar cells
    • Chang, Y.J.; Watanabe, M.; Chou, P.; Chow, T.J. [2.2]Paracyclophane as a bridging unit in the design of organic dyes for sensitized solar cells. Chem. Commun. 2012, 48, 726-728.
    • (2012) Chem. Commun. , vol.48 , pp. 726-728
    • Chang, Y.J.1    Watanabe, M.2    Chou, P.3    Chow, T.J.4
  • 13
    • 33744493167 scopus 로고    scopus 로고
    • High-performance organic light-emitting diodes based on intramolecular charge-transfer emission from donor-acceptor molecules: Significance of electron-donor strength and molecular geometry
    • Kulkarni, A.P.; Kong, X.; Jenekhe, S.A. High-performance organic light-emitting diodes based on intramolecular charge-transfer emission from donor-acceptor molecules: Significance of electron-donor strength and molecular geometry. Adv. Funct. Mater. 2006, 16, 1057-1066.
    • (2006) Adv. Funct. Mater. , vol.16 , pp. 1057-1066
    • Kulkarni, A.P.1    Kong, X.2    Jenekhe, S.A.3
  • 14
    • 33845203435 scopus 로고    scopus 로고
    • Light-emitting organic solar cells based on a 3D conjugated system with internal charge transfer
    • Cravino, A.; Leriche, P.; Alév̂que, O.; Roquet, S.; Roncali, J. Light-emitting organic solar cells based on a 3D conjugated system with internal charge transfer. Adv. Mater. 2006, 18, 3033-3037.
    • (2006) Adv. Mater. , vol.18 , pp. 3033-3037
    • Cravino, A.1    Leriche, P.2    Alév̂que, O.3    Roquet, S.4    Roncali, J.5
  • 15
    • 0037134605 scopus 로고    scopus 로고
    • New fluorescent "Off-On" behavior of 9-anthryl aromatic amides through controlling the twisted intramolecular charge transfer relaxation process by complexation with metal ions
    • Morozumi, T.; Anada, T.; Nakamura, H. New fluorescent "Off-On" behavior of 9-anthryl aromatic amides through controlling the twisted intramolecular charge transfer relaxation process by complexation with metal ions. J. Phys. Chem. B 2001, 105, 2923-2931.
    • (2001) J. Phys. Chem. B , vol.105 , pp. 2923-2931
    • Morozumi, T.1    Anada, T.2    Nakamura, H.3
  • 16
    • 79959464682 scopus 로고    scopus 로고
    • New sensing mechanisms for design of fluorescent chemosensors emerging in recent years
    • Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. New sensing mechanisms for design of fluorescent chemosensors emerging in recent years. Chem. Soc. Rev. 2011, 40, 3483-3495.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 3483-3495
    • Wu, J.1    Liu, W.2    Ge, J.3    Zhang, H.4    Wang, P.5
  • 17
    • 33644518997 scopus 로고    scopus 로고
    • PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform
    • Hall, M.J.; Allen, L.T.; O'Shea, D.F. PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform. Org. Biomol. Chem. 2006, 4, 776-780.
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 776-780
    • Hall, M.J.1    Allen, L.T.2    O'shea, D.F.3
  • 18
    • 0142196979 scopus 로고    scopus 로고
    • Triple fluorescence of 4-(1,4,8,11-tetraazacyclotetradecyl)benzonitrile
    • Choi, L. Triple fluorescence of 4-(1,4,8,11-tetraazacyclotetradecyl) benzonitrile. Chem. Commun. 1998, 1998, 893-894.
    • (1998) Chem. Commun. , vol.1998 , pp. 893-894
    • Choi, L.1
  • 20
    • 0001118952 scopus 로고
    • Excimer versus TICT state formation in polar solutions of methyl 4-(N,N-dimethylamino)benzoate
    • Revill, J.A.T.; Browna, R.G. Excimer versus TICT state formation in polar solutions of methyl 4-(N,N-dimethylamino)benzoate. Chem. Phys. Lett. 1992, 188, 433-438.
    • (1992) Chem. Phys. Lett. , vol.188 , pp. 433-438
    • Revill, J.A.T.1    Browna, R.G.2
  • 21
    • 0142228080 scopus 로고
    • Hydrophobic effects on photophysical and photochemical processes: Excimer fluorescence and aggregate formation of long-chain alkyl 4-(N,N-dimethylamino) benzoate in water-Organic binary mixtures
    • Zhen, Z.; Tung, C. Hydrophobic effects on photophysical and photochemical processes: Excimer fluorescence and aggregate formation of long-chain alkyl 4-(N,N-dimethylamino) benzoate in water-Organic binary mixtures. Chem. Phys. Lett. 1991, 180, 211-215.
    • (1991) Chem. Phys. Lett. , vol.180 , pp. 211-215
    • Zhen, Z.1    Tung, C.2
  • 22
    • 84961986830 scopus 로고    scopus 로고
    • Revisiting fluorenone photophysics via dipolar fluorenone derivatives
    • Estrada, L.A.; Yarnell, J.E.; Neckers, D.C. Revisiting fluorenone photophysics via dipolar fluorenone derivatives. J. Phys. Chem. A 2011, 115, 6366-6375.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 6366-6375
    • Estrada, L.A.1    Yarnell, J.E.2    Neckers, D.C.3
  • 23
    • 80052855844 scopus 로고    scopus 로고
    • Spectral signature of 2-[4-(dimethylamino)styryl]-1-methylquinolinium iodide: A case of negative solvatochromism in water
    • Sahoo, D.; Bhattacharya, P.; Chakravorti, S. Spectral signature of 2-[4-(dimethylamino)styryl]-1-methylquinolinium iodide: A case of negative solvatochromism in water. J. Phys. Chem. B 2011, 115, 10983-10989.
    • (2011) J. Phys. Chem. B , vol.115 , pp. 10983-10989
    • Sahoo, D.1    Bhattacharya, P.2    Chakravorti, S.3
  • 24
    • 70649093940 scopus 로고    scopus 로고
    • Synthesis and photoluminescence properties of p-extended fluorene derivatives: The first example of a fluorescent solvatochromic nitro-group-containing dye with a high fluorescence quantum yield
    • Kotaka, H.; Konishi, G.; Mizuno, K. Synthesis and photoluminescence properties of p-extended fluorene derivatives: The first example of a fluorescent solvatochromic nitro-group-containing dye with a high fluorescence quantum yield. Tetrahedron Lett. 2010, 51, 181-184.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 181-184
    • Kotaka, H.1    Konishi, G.2    Mizuno, K.3
  • 25
    • 0030584191 scopus 로고    scopus 로고
    • Solvent and concentration effects on the steady state fluorescence of fluorenone
    • Rani, S.A.; Sobhanadri, J.; Rao, T.A.P. Solvent and concentration effects on the steady state fluorescence of fluorenone. J. Photochem. Photobiol. A 1996, 94, 1-5.
    • (1996) J. Photochem. Photobiol. A , vol.94 , pp. 1-5
    • Rani, S.A.1    Sobhanadri, J.2    Rao, T.A.P.3
  • 26
    • 0001710347 scopus 로고
    • Electronic spectrum of fluorenone
    • Kuboyama, A. Electronic spectrum of fluorenone. Bull. Chem. Soc. Jpn. 1964, 37, 1540-1544.
    • (1964) Bull. Chem. Soc. Jpn. , vol.37 , pp. 1540-1544
    • Kuboyama, A.1
  • 27
    • 0030662641 scopus 로고    scopus 로고
    • Quenching processes in hydrogen-bonded pairs: Interactions of excited fluorenone with alcohols and phenols
    • Biczók, L.; Bérces, T.; Linschitz, H. Quenching processes in hydrogen-bonded pairs: Interactions of excited fluorenone with alcohols and phenols. J. Am. Chem. Soc. 1997, 119, 11071-11077.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11071-11077
    • Biczók, L.1    Bérces, T.2    Linschitz, H.3
  • 28
    • 0000431034 scopus 로고
    • Picosecond time-resolved spectroscopy and the intersystem crossing rates of anthrone and fluorenone
    • Kobayashi, T.; Nagakura, S. Picosecond time-resolved spectroscopy and the intersystem crossing rates of anthrone and fluorenone. Chem. Phys. Lett. 1976, 43, 429-434.
    • (1976) Chem. Phys. Lett. , vol.43 , pp. 429-434
    • Kobayashi, T.1    Nagakura, S.2
  • 30
    • 0000304834 scopus 로고
    • Spectroscopic properties of the lower lying excited states of fluorenone
    • Yoshihara, K.; Kearns, D.R. Spectroscopic properties of the lower lying excited states of fluorenone. J. Chem. Phys. 1966, 45, 1991-1999.
    • (1966) J. Chem. Phys. , vol.45 , pp. 1991-1999
    • Yoshihara, K.1    Kearns, D.R.2
  • 31
    • 84859593999 scopus 로고    scopus 로고
    • On the role of hydrogen bonds in photoinduced electron-transfer dynamics between 9-fluorenone and amine solvents
    • Ghosh, H.N.; Adamczyk, K.; Verma, S.; Dreyer, J.; Nibbering, E.T.J. On the role of hydrogen bonds in photoinduced electron-transfer dynamics between 9-fluorenone and amine solvents. Chem. Eur. J. 2012, 18, 4930-4937.
    • (2012) Chem. Eur. J. , vol.18 , pp. 4930-4937
    • Ghosh, H.N.1    Adamczyk, K.2    Verma, S.3    Dreyer, J.4    Nibbering, E.T.J.5
  • 32
    • 35148865333 scopus 로고    scopus 로고
    • Ultrafast hydrogen bond strengthening of the photoexcited fluorenone in alcohols for facilitating the fluorescence quenching
    • Zhao, G.; Han, K. Ultrafast hydrogen bond strengthening of the photoexcited fluorenone in alcohols for facilitating the fluorescence quenching. J. Phys. Chem. A 2007, 111, 9218-9223.
    • (2007) J. Phys. Chem. A , vol.111 , pp. 9218-9223
    • Zhao, G.1    Han, K.2
  • 33
    • 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
    • Zhao, G.; Han, K. 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 2009, 113, 14329-14335.
    • (2009) J. Phys. Chem. A , vol.113 , pp. 14329-14335
    • Zhao, G.1    Han, K.2
  • 34
    • 0000774889 scopus 로고    scopus 로고
    • Photophysical properties of intramolecular charge-transfer excited singlet state of aminofluorenone derivatives
    • Yatsuhashi, T.; Nakajima, Y.; Shimada, T.; Inoue, H. Photophysical properties of intramolecular charge-transfer excited singlet state of aminofluorenone derivatives. J. Phys. Chem. A 1998, 102, 3018-3024.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3018-3024
    • Yatsuhashi, T.1    Nakajima, Y.2    Shimada, T.3    Inoue, H.4
  • 35
    • 70350733534 scopus 로고    scopus 로고
    • Synthesis and photophysics of ambipolar fluoren-9-ylidene malononitrile derivatives
    • Estrada, L.A.; Neckers, D.C. Synthesis and photophysics of ambipolar fluoren-9-ylidene malononitrile derivatives. J. Org. Chem. 2009, 74, 8484-8487.
    • (2009) J. Org. Chem. , vol.74 , pp. 8484-8487
    • Estrada, L.A.1    Neckers, D.C.2
  • 36
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 37
    • 0001658891 scopus 로고
    • Electron transfer and the structural changes in the excited state
    • Grabowski, Z.R. Electron transfer and the structural changes in the excited state. Pure Appl. Chem. 1992, 64, 1249-1255.
    • (1992) Pure Appl. Chem. , vol.64 , pp. 1249-1255
    • Grabowski, Z.R.1
  • 38
    • 5844252510 scopus 로고
    • Solvatochromic dyes as solvent polarity indicators
    • Reichardt, C. Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94, 2319-2358.
    • (1994) Chem. Rev. , vol.94 , pp. 2319-2358
    • Reichardt, C.1


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