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

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

Hajime Maeda 1,* email, Tomohiro Maeda 2  and Kazuhiko Mizuno 2,* email
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; in revised form: 21 April 2012 / Accepted: 23 April 2012 / Published: 3 May 2012
(This article belongs to the Special Issue Fluorophores - The Fluorescent Toolbox in Biological and Biomedical Research)
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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

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MDPI and ACS Style

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.

AMA Style

Maeda H, Maeda T, Mizuno K. Absorption and Fluorescence Spectroscopic Properties of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives. Molecules. 2012; 17(5):5108-5125.

Chicago/Turabian Style

Maeda, Hajime; Maeda, Tomohiro; Mizuno, Kazuhiko. 2012. "Absorption and Fluorescence Spectroscopic Properties of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives." Molecules 17, no. 5: 5108-5125.

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