NDLI: Investigation of the photoisomerisation process in four p-benzoxazoyl-substituted stilbenes

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Photochemical & Photobiological Sciences Vol - 9 Issue - 2

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Photochemical & Photobiological Sciences Vol -2

Investigation of the photoisomerisation process in four p-benzoxazoyl-substituted stilbenes

Content Provider	Royal Society of Chemistry (RSC)
Author	Mac, Marek Leśniewski, Sebastian Danel, Andrzej Kulig, Ewa Gorycka, Sabina Uchacz, Tomasz Górz, Katarzyna
Copyright Year	2010
Abstract	Fluorescence properties and trans–cis photoisomerisation of the benzoxazole derivatives 2-[4-(E)-(styryl)phenyl]benzoxazole (I), 2-{4-[(E)-2-(4-methoxyphenyl)vinyl]phenyl}benzoxazole (II), {4-[(E)-2-(4-benzoxazol-2-yl-phenyl)vinyl]phenyl}dimethylamine (III) and {4-[(E)-2-(4-benzoxazol-2-yl-phenyl)vinyl]phenyl}diphenylamine (IV) have been investigated in solvents of different polarities. It was found that these compounds exhibit efficient fluorescence with quantum yields and lifetimes strongly dependent on solvent polarity, although only compounds III and IV possess a significant charge transfer character in solvents of medium and high polarities. In addition, the photoisomerisation quantum efficiency depends strongly on the substitution of the phenyl ring in the electron donor moiety. A strong dependence of the quantum efficiency of the photoisomerisation on solvent was established. That quantity depends linearly on the non-radiative quantum yield of the deactivation of the excited singlet state for all investigated compounds. These results are consistent with a singlet state mechanism of the photoprocess. For compounds III and IV, with strong electron donors (N,N-dimethylaniline and triphenylamine), the molecule in the excited state trans configuration is more stabilized by solvent polarity than in the perpendicular form which causes more efficient isomerisation in nonpolar solvents. For compounds I and II the energy of the perpendicular configuration decreases more rapidly than that of the trans configuration when solvent polarity increases. In this case the energy barrier decreases with increasing solvent polarity. This makes the photoisomerisation process easier in polar solvents.
Starting Page	357
Ending Page	364
Page Count	8
File Format	HTM / HTML PDF
ISSN	1474905X
Volume Number	9
Issue Number	3
Journal	Photochemical & Photobiological Sciences
DOI	10.1039/b9pp00098d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Dimethylaniline Isomerization Benzoxazole Dimethylamine Phenyl group Diphenylamine Fluorescence in the life sciences Correlation and dependence Solvent Triphenylamine Quantum tunnelling Nucleophile
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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