Anthracene-fused BODIPYs as near-infrared dyes with high photostability

Org Lett. 2011 Nov 18;13(22):6026-9. doi: 10.1021/ol202493c. Epub 2011 Oct 20.

Abstract

An anthracene unit was successfully fused to the zigzag edge of a boron dipyrromethene (BODIPY) core by an FeCl(3)-mediated oxidative cyclodehydrogenation reaction. Meanwhile, a dimer was also formed by both intramolecular cyclization and intermolecular coupling. The anthracene-fused BODIPY monomer 7a and dimer 7b showed small energy gaps (∼1.4 eV) and near-infrared absorption/emission. Moreover, they exhibited high photostability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry*
  • Boron Compounds / chemical synthesis*
  • Dimerization
  • Fluorescent Dyes / chemical synthesis*
  • Models, Molecular
  • Molecular Structure
  • Photochemical Processes
  • Spectroscopy, Near-Infrared

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Anthracenes
  • Boron Compounds
  • Fluorescent Dyes
  • anthracene