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, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

7 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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Hydrogen Bonding
Complexation
Quenching
pyridines
Hydrogen bonds
quenching
Fluorescence
hydrogen
fluorescence
curvature
Derivatives
Fluorophores
Ground state
Hydrogen
plots
pyridine
ground state

Keywords

  • Complexes
  • Density functional calculations
  • Fluorescence
  • Quenching
  • Solvatochromism

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Medicine(all)

Cite this

Solvatochromic study of highly fluorescent alkylated isocyanonaphthalenes, their p-stacking, hydrogen-bonding complexation, and quenching with pyridine. / Nagy, Miklós; Rácz, Dávid; Lázár, László; Purgel, Mihály; Ditrói, Tamás; Zsuga, M.; Kéki, S.

In: ChemPhysChem, Vol. 15, No. 16, 28.08.2014, p. 3614-3625.

Research output: Contribution to journalArticle

Nagy, Miklós ; Rácz, Dávid ; Lázár, László ; Purgel, Mihály ; Ditrói, Tamás ; Zsuga, M. ; Kéki, S. / Solvatochromic study of highly fluorescent alkylated isocyanonaphthalenes, their p-stacking, hydrogen-bonding complexation, and quenching with pyridine. In: ChemPhysChem. 2014 ; Vol. 15, No. 16. pp. 3614-3625.
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AU - Nagy, Miklós

AU - Rácz, Dávid

AU - Lázár, László

AU - Purgel, Mihály

AU - Ditrói, Tamás

AU - Zsuga, M.

AU - Kéki, S.

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N2 - 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.

AB - 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.

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