I. Craig, H. Duong, F. Wudl
Aug 6, 2009
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Influential Citations
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Journal
Chemical Physics Letters
Abstract
Abstract The isoquinolinone derivative 2-methyl-1,4-diphenylbenzo[g]isoquinolin-3(2 H )-one (MDP-BIQ) shows dual fluorescence emission with band positions and intensities that depend sensitively on the solvent. We show that this behavior arises from the fact that MDP-BIQ has two valence tautomers, one aromatic and one conjugated but non-aromatic, each of which are separately fluorescent. The aromatic tautomer, which has significant zwitterionic character, is stabilized by trace amounts of hydrogen-bond donors or Lewis acids. The relatively high fluorescence quantum yield of the aromatic tautomer (0.127 versus 2.4 × 10 −3 for the non-aromatic tautomer) makes this and similar molecules outstanding candidates for use in sensors and other optoelectronic applications.