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Molecules 2012, 17(5), 5108-5125; doi:10.3390/molecules17055108

Absorption and Fluorescence Spectroscopic Properties of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives

1
Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan
2
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
*
Authors to whom correspondence should be addressed.
Received: 13 February 2012 / Revised: 21 April 2012 / Accepted: 23 April 2012 / Published: 3 May 2012
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Abstract

Silyl-substituted naphthalene derivatives at the 1- and 1,4-positions were synthesized and their UV absorption, fluorescence spectroscopic properties, and fluorescence lifetimes were determined. Analysis of the results shows that the introduction of silyl groups at these positions of the naphthalene chromophore/fluorophore causes shifts of the absorption maxima to longer wavelengths and increases in fluorescence intensities. Bathochromic shifts of the absorption maxima and increases in fluorescence intensities are also promoted by the introduction of methoxy and cyano groups at the naphthalene 4- and 5-positions. In addition, the fluorescence of 9,10-dicyanoanthracene is efficiently quenched by these naphthalene derivatives with Stern-Volmer plot calculated rate constants that depend on the steric bulk of the silyl groups.
Keywords: naphthalene; organosilicon compounds; fluorescence; absorption; fluorescence quenching; fluorescence lifetime; fluorescence quantum yield naphthalene; organosilicon compounds; fluorescence; absorption; fluorescence quenching; fluorescence lifetime; fluorescence quantum yield
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Maeda, H.; Maeda, T.; Mizuno, K. Absorption and Fluorescence Spectroscopic Properties of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives. Molecules 2012, 17, 5108-5125.

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