Substituent-dependent photoinduced intramolecular charge transfer in N-aryl-substituted trans-4-aminostilbenes

Jye Shane Yang, Kang Ling Liau, Chin Min Wang, Chung Yu Hwang

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158 Scopus citations

Abstract

The photochemical behavior of trans-4-(N-arylamino)stilbene (1, aryl = 4-substituted phenyl) in solvents more polar than THF is strongly dependent on the substituent in the N-aryl group. This is attributed to the formation of a twisted intramolecular charge transfer (TICT) state for those with a methoxy (1OM), methoxycarbonyl (1CO), or cyano (1CN) substituent but not for those with a methyl (1Me), hydrogen (1H), chloro (1Cl), or trifluoromethyl (1CF) substituent. On the basis of the ring-bridged model compounds 3-6, the TICT states for 1CN and 1CO result from the twisting of the anilino-benzonitrilo C-N bond, but for 1OM it is from the twisting of the stilbenyl-anilino C-N bond, both of which are distinct from the TICT states previously proposed for N,N-dimethylaminostilbenes.

Original languageEnglish
Pages (from-to)12325-12335
Number of pages11
JournalJournal of the American Chemical Society
Volume126
Issue number39
DOIs
StatePublished - 6 Oct 2004

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