An 2-(2'-aminophenyl)benzoxazole-based OFF-ON fluorescent chemosensor for Zn2+ in aqueous solution

Org Biomol Chem. 2011 Apr 7;9(7):2345-9. doi: 10.1039/c0ob00983k. Epub 2011 Feb 11.

Abstract

A water-soluble fluorescent sensor, 1, based on the "receptor-spacer-fluorophore" [2-(2'-aminophenyl)benzoxazole-amide-2-picolylamine] sensor platform, demonstrates the high sensitivity for Zn(2+) with a 25-fold fluorescence enhancement upon chelation to Zn(2+) and also exhibits high selectivity to Zn(2+) over other metal ions. X-ray crystal structure of Zn(2+) complex reveals that the amide oxygen (O2) cooperates with 2-picolylamine unit (N3, N4) as a receptor bind Zn(2+).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoxazoles / chemistry*
  • Cations, Divalent / chemistry
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Solutions / chemistry
  • Zinc / chemistry*

Substances

  • 2-(2'-aminophenyl)benzoxazole
  • Benzoxazoles
  • Cations, Divalent
  • Fluorescent Dyes
  • Solutions
  • Zinc