Synthesis and functionalization of asymmetrical benzo-fused BODIPY dyes

J Org Chem. 2010 Sep 3;75(17):6035-8. doi: 10.1021/jo101164a.

Abstract

A series of asymmetrical benzo-fused BODIPY dyes were synthesized from the Sonogashira coupling and nucleophilic substitution reactions on the 3-halogenated benzo-fused BODIPY, generated from readily available 3-halogeno-1-formylisoindoles in a two-step synthetic procedure. This novel BODIPY platform provides an easy path for the linking of BODIPY fluorophore to various desired functionalities as demonstrated in this work. Most of the resulting BODIPY dyes show long-wavelength absorption and fluorescence emission, with good fluorescence quantum yields and long fluorescence lifetimes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

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