Spectroscopic properties of aromatic dicarboximides. Part 2. - Substituent effect on the photophysical properties of N-phenyl-1,2-naphthalimide

Attila Demeter, Tibor Bérces, László Biczók, Véronique Wintgens, Pierre Valat, Jean Kossanyi

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Absorption and fluorescence spectra, fluorescence decay times, fluorescence quantum yields and triplet yields have been determined for N-phenyl-1,2- naphthalimide and its phenyl-substituted methyl derivatives in different solvents. N-Phenyl-1,2-naphthalimide emits long-wavelength fluorescence in hexane (λfmax = 550 nm) which is red shifted by methyl substitution at the meta and para positions of the phenyl ring and by using a solvent of higher polarity. The fluorescence decays on the sub-nanosecond timescale. When the N-phenyl-1,2-naphthalimide has o-methyl substituents in the phenyl group, they emit dual fluorescence. The location of the short-wavelength component is constant while that of the long-wavelength component is blue shifted as a result of o-methyl substitution. Ortho substitution also increases the decay time of the long-wavelength fluorescence. The results are explained in terms of vibronic interaction between the S 1(ππ*) and S2(nπ*) excited states (pseudo-Jahn-Teller effect) which is enhanced by solvent relaxation and twisting of the phenyl ring towards a coplanar geometry.

Original languageEnglish
Pages (from-to)2635-2641
Number of pages7
JournalJournal of the Chemical Society, Faraday Transactions
Issue number18
Publication statusPublished - Dec 1 1994


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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