The effect of substituents on the response of 3,4-dihydro-3-(2-oxo-2- phenylethylidene)-quinoxalin-2(1H)-one derivatives toward binding of Cu 2+

Efrat Korin, Beny Cohen, Yue Xia Bai, Cheng Chu Zeng, James Y. Becker

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A new series of fluorogenic chelating reagents based on phenylethylidene-3,4-dihydro-1H-quinoxalin-2-one with different substituents (attached either to the quinoxaline-2-one (3) or phenyl ring (4)) have been investigated to examine the effect of the substituent (nature/position) on the spectral properties and response toward Cu 2+ in the presence of other metal cations, in ethanol. It was found that all of the examined ligands exhibit a pronounced response to Cu 2+ addition resulting in a red-shift in the UV-vis spectra and a strong quenching in the fluorescence spectra. Among the ligands examined, 3a exhibits the highest selectivity toward various metal cations. In general it appears that the best response selectivity of these ligands toward Cu 2+ ion is obtained by either EDG in 3 or EWG in 4. For example, the fluorescence intensity of 3a (with OMe substituent) increases to about three times that of the unsubstituted derivative.

Original languageEnglish
Pages (from-to)7450-7455
Number of pages6
JournalTetrahedron
Volume68
Issue number36
DOIs
StatePublished - 9 Sep 2012

Keywords

  • Chelating reagent
  • Chemosensors
  • Cu recognition
  • Fluorescence
  • Quinoxalinone dérivatives

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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