Twisted Intramolecular Charge Transfer States in 2-Arylbenzotriazoles: Fluorescence Deactivation via Intramolecular Electron Transfer Rather Than Proton Transfer
Ultraviolet absorbers such as Tinuvin P (2-(2-hydroxy-5-methylphenyl)benzotriazole), 1, achieve their exceptional photostabilities as a result of deactivation of excited singlet states through excited state intramolecular proton transfer (ESIPT). Adding a methyl group to the 6‘ position of 2-arylben...
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| Published in | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 106; no. 34; pp. 7680 - 7689 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
29.08.2002
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| Online Access | Get full text |
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| Abstract | Ultraviolet absorbers such as Tinuvin P (2-(2-hydroxy-5-methylphenyl)benzotriazole), 1, achieve their exceptional photostabilities as a result of deactivation of excited singlet states through excited state intramolecular proton transfer (ESIPT). Adding a methyl group to the 6‘ position of 2-arylbenzotriazoles reveals an additional excited singlet state deactivation mechanism in this class of molecules which does not require intramolecular hydrogen bonding. Steady state fluorescence and fluorescence lifetime measurements for a series of 6‘-methyl-2-arylbenzotriazoles provides compelling evidence for a twisted intramolecular charge transfer (TICT) mechanism of excited singlet state deactivation. Due to the steric requirements of the 6‘-methyl group, conformations are favored in which the phenyl and triazole rings are no longer coplanar. In the case of compound 11 (2-(6-methoxy-2,3-dimethylphenyl)-2H-benzotriazole), the presence of a 2‘-methoxy group enhances nonplanarity and results in large deactivation rates. Compound 12 (2-(6-methoxy-2,3-dimethylphenyl)-5-(trifluoromethyl)-2H-benzotriazole), which possesses both twist and enhanced donor/acceptor properties, undergoes the most efficient fluorescence quenching for the methoxyarylbenzotriazoles. Compounds with both a 6‘-methyl and a hydroxy group on the phenyl ring exhibit diffusion controlled quenching (k q = 2 × 1010 M-1 s-1) by DMSO. This quenching appears to result from either partial or complete excited state proton transfer to DMSO, which enhances TICT deactivation of the singlet excited state. |
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| AbstractList | Ultraviolet absorbers such as Tinuvin P (2-(2-hydroxy-5-methylphenyl)benzotriazole), 1, achieve their exceptional photostabilities as a result of deactivation of excited singlet states through excited state intramolecular proton transfer (ESIPT). Adding a methyl group to the 6‘ position of 2-arylbenzotriazoles reveals an additional excited singlet state deactivation mechanism in this class of molecules which does not require intramolecular hydrogen bonding. Steady state fluorescence and fluorescence lifetime measurements for a series of 6‘-methyl-2-arylbenzotriazoles provides compelling evidence for a twisted intramolecular charge transfer (TICT) mechanism of excited singlet state deactivation. Due to the steric requirements of the 6‘-methyl group, conformations are favored in which the phenyl and triazole rings are no longer coplanar. In the case of compound 11 (2-(6-methoxy-2,3-dimethylphenyl)-2H-benzotriazole), the presence of a 2‘-methoxy group enhances nonplanarity and results in large deactivation rates. Compound 12 (2-(6-methoxy-2,3-dimethylphenyl)-5-(trifluoromethyl)-2H-benzotriazole), which possesses both twist and enhanced donor/acceptor properties, undergoes the most efficient fluorescence quenching for the methoxyarylbenzotriazoles. Compounds with both a 6‘-methyl and a hydroxy group on the phenyl ring exhibit diffusion controlled quenching (k q = 2 × 1010 M-1 s-1) by DMSO. This quenching appears to result from either partial or complete excited state proton transfer to DMSO, which enhances TICT deactivation of the singlet excited state. |
| Author | Suhadolnik, Joseph C Maliakal, Ashok DeBellis, Anthony D Wood, Mervin G Ravichandran, Ravi Turro, Nicholas J Lau, Jacqueline Lem, George |
| Author_xml | – sequence: 1 givenname: Ashok surname: Maliakal fullname: Maliakal, Ashok – sequence: 2 givenname: George surname: Lem fullname: Lem, George – sequence: 3 givenname: Nicholas J surname: Turro fullname: Turro, Nicholas J – sequence: 4 givenname: Ravi surname: Ravichandran fullname: Ravichandran, Ravi – sequence: 5 givenname: Joseph C surname: Suhadolnik fullname: Suhadolnik, Joseph C – sequence: 6 givenname: Anthony D surname: DeBellis fullname: DeBellis, Anthony D – sequence: 7 givenname: Mervin G surname: Wood fullname: Wood, Mervin G – sequence: 8 givenname: Jacqueline surname: Lau fullname: Lau, Jacqueline |
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| Snippet | Ultraviolet absorbers such as Tinuvin P (2-(2-hydroxy-5-methylphenyl)benzotriazole), 1, achieve their exceptional photostabilities as a result of deactivation... |
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| Title | Twisted Intramolecular Charge Transfer States in 2-Arylbenzotriazoles: Fluorescence Deactivation via Intramolecular Electron Transfer Rather Than Proton Transfer |
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