Effect of the substitution position on the electronic and solvatochromic properties of isocyanoaminonaphthalene (ICAN) fluorophores

Sándor Lajos Kovács, Miklós Nagy, Péter Pál Fehér, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

Abstract

The properties of 1,4-isocyanoaminonaphthalene (1,4-ICAN) and 2,6-isocyanoaminonaphthalene (2,6-ICAN) isomers are discussed in comparison with those of 1,5-isocyanoaminonaphthalene (1,5-ICAN), which exhibits a large positive solvatochromic shift similar to that of Prodan. In these isocyanoaminonaphthalene derivatives, the isocyano and the amine group serve as the donor and acceptor moieties, respectively. It was found that the positions of the donor and the acceptor groups in these naphthalene derivatives greatly influence the Stokes and solvatochromic shifts, which decrease in the following order: 1,5-ICAN > 2,6-ICAN > 1,4-ICAN. According to high-level quantum chemical calculations, this order is well correlated with the charge transfer character of these compounds upon excitation. Furthermore, unlike 1,5-ICAN, the 1,4-ICAN and 2,6-ICAN isomers showed relatively high quantum yields in water, that were determined to be 0.62 and 0.21, respectively. In addition, time-resolved fluorescence experiments revealed that both the radiative and non-radiative decay rates for these three ICAN isomers varied unusually with the solvent polarity parameter ET(30). The explanations of the influence of the solvent polarity on the resulting steady-state and time-resolved fluorescence emission spectra are also discussed.

Original languageEnglish
Article number2434
JournalMolecules
Volume24
Issue number13
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Fluorophores
Isomers
Substitution reactions
isomers
Fluorescence
substitutes
polarity
electronics
Derivatives
Amines
fluorescence
shift
Quantum yield
naphthalene
decay rates
Water
Charge transfer
amines
emission spectra
charge transfer

Keywords

  • Electronic absorption
  • Fluorescence
  • Isocyano-aminonaphthalenes
  • Push-pull dyes
  • Solvatochromism

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Effect of the substitution position on the electronic and solvatochromic properties of isocyanoaminonaphthalene (ICAN) fluorophores. / Kovács, Sándor Lajos; Nagy, Miklós; Fehér, Péter Pál; Zsuga, M.; Kéki, S.

In: Molecules, Vol. 24, No. 13, 2434, 01.01.2019.

Research output: Contribution to journalArticle

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