Synthesis and photochemical behavior of donor-acceptor systems obtained from chloro-1,4-naphthoquinone attached to trans-aminostilbenes

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19 Scopus citations

Abstract

2-Chloro-1,4-naphthoquinone was covalently attached to six differently substituted and positional isomers of trans-aminostilbene, forming a novel donor-acceptor system (QST), in which a good fluorophore is bonded via an NH group to an active redox quencher. The new systems were characterized by FT-IR, 1H NMR, HR-MS, UV-Vis and fluorescence spectroscopy. The redox state of the system QST/QH2ST controls its photochemical properties. While the QST's behave as an 'auto-quenching system' and are non-fluorescent, the reduced hydroquinonic system (QH2ST) affects appreciably the emission properties of the molecule.

Original languageEnglish
Pages (from-to)2939-2945
Number of pages7
JournalTetrahedron
Volume59
Issue number16
DOIs
StatePublished - 14 Apr 2003

Keywords

  • Aminostilbene
  • Fluorescence quenching
  • Hydroquinone
  • Molecular switching system
  • Quinone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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