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

Miklós Nagy, Dávid Rácz, László Lázár, Mihály Purgel, Tamás Ditrói, Miklós Zsuga, Sándor Kéki

Research output: Article

8 Citations (Scopus)

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 p-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 p-stacked complex.

Original languageEnglish
Pages (from-to)3614-3625
Number of pages12
JournalChemPhysChem
Volume15
Issue number16
DOIs
Publication statusPublished - aug. 28 2014

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ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Physical and Theoretical Chemistry

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