Solvatochromic study of highly fluorescent alkylated isocyanonaphthalenes, their π-stacking, hydrogen-bonding complexation, and quenching with pyridine

Nagy, Miklós and Rácz, Dávid and Lázár, László and Purgel, Mihály and Ditrói, Tamás and Zsuga, Miklós and Kéki, Sándor (2014) Solvatochromic study of highly fluorescent alkylated isocyanonaphthalenes, their π-stacking, hydrogen-bonding complexation, and quenching with pyridine. CHEMPHYSCHEM, 15 (16). pp. 3614-3625. ISSN 1439-4235

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Abstract

Mono- and dialkylated derivatives of 1-amino-5-isocyanonaphthalene (ICAN) were studied as new members of a multifunctional, easy-to-prepare fluorophore family, which showed excellent solvatochromic properties. The monoallyl derivative and the starting ICAN exhibited strong fluorescence quenching in the presence of small amounts of pyridine. The formation of a hydrogen-bonded ground-state pyridine complex was detected; however, analysis of quantum chemical calculations suggested the presence of an additional π-stacked pyridine complex. The Stern-Volmer plot of the quenching process exhibited a downward curvature and after reaching a minimum the fluorescence intensity increased back to a significant level at high pyridine concentrations. Significant fluorescence was observed even in pure pyridine. A new mechanism and a simple mathematical equation were derived to explain the downward curvature and the remaining fluorescence by the formation of a fluorescent π-stacked complex. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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