M. Venanzi, G. Bocchinfuso, A. Palleschi
Mar 15, 2005
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Influential Citations
5
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Journal
Journal of Photochemistry and Photobiology A-chemistry
Abstract
Abstract Fluorescent derivatives of benzo[ b ]thiophene were synthesized by C C and C N palladium catalysed cross-couplings of bromobenzenes with 3-(benzo[ b ]thienyl)boronic acid and bromo- or aminobenzenes with 7-amino or 7-bromobenzo[ b ]thiophene, respectively. The photophysical behaviour of the coupled compounds was investigated in acetonitrile, showing that a delicate balance between the delocalization of the electronic distribution over the entire molecule and the extent of intramolecular charge transfer interactions controls the excited-state relaxation pathway. Some of the new benzo[ b ]thiophene derivatives were linked to the β-carbon of alanine to obtain quasi-isosteric analogues of naturally occurring fluorescent amino acids.