Journal
CHEMICAL PHYSICS LETTERS
Volume 477, Issue 4-6, Pages 319-324Publisher
ELSEVIER
DOI: 10.1016/j.cplett.2009.07.041
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Funding
- NSF [CHE-0527015, CHE-9974928, CHE-0116853]
- ONR [N-00014-04-1-0410]
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The isoquinolinone derivative 2-methyl-1,4-diphenylbenzo[g] isoquinolin-3(2H)-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 x 10(-3) for the non-aromatic tautomer) makes this and similar molecules outstanding candidates for use in sensors and other optoelectronic applications. (C) 2009 Elsevier B. V. All rights reserved.
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