Solvatochromic Study of Highly Fluorescent Alkylated Isocyanonaphthalenes, Their π-Stacking, Hydrogen-Bonding Complexation, and Quenching with Pyridine
Dr. Miklós Nagy
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDávid Rácz
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDr. László Lázár
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDr. Mihály Purgel
MTA-DE Homogeneous Catalysis and Reaction Mechanisms Research Group University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary)
Search for more papers by this authorTamás Ditrói
Department of Inorganic and Analytical Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary)
Search for more papers by this authorDr. Miklós Zsuga
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorCorresponding Author
Prof. Dr. Sándor Kéki
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662Search for more papers by this authorDr. Miklós Nagy
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDávid Rácz
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDr. László Lázár
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorDr. Mihály Purgel
MTA-DE Homogeneous Catalysis and Reaction Mechanisms Research Group University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary)
Search for more papers by this authorTamás Ditrói
Department of Inorganic and Analytical Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary)
Search for more papers by this authorDr. Miklós Zsuga
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Search for more papers by this authorCorresponding Author
Prof. Dr. Sándor Kéki
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662
Department of Applied Chemistry, University of Debrecen, 4032 Debrecen, Egyetem tér 1 (Hungary), Fax: (+36) 52-518662Search for more papers by this authorGraphical Abstract
Dyeing to quench: The solvatochromic properties of novel, effective, alkylated, aminoisocyanonaphthalene-based fluorophores are investigated. Their complexation and special quenching with pyridine is studied in detail (see picture; 1: cyclohexane, 2: cyclohexane/pyridine, 3: pyridine).
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.
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