Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

Org Biomol Chem. 2015 Jun 7;13(21):6031-8. doi: 10.1039/c5ob00499c.

Abstract

A high-yielding method for the direct thiocyanation of BODIPY dyes is described. In 1,3-dimethyl BODIPYs, the thiocyanato group adds at position 2, whereas the insertion occurs at position 5 in 3-amino BODIPYs. The transformation of the thiocyanato group enables the synthesis of thioalkylated BODIPYs. 2-Thioalkylated BODIPYs and 3-thiocyanato-5-piperidino BODIPYs exhibit interesting spectroscopical features. Hence, the described synthetic methodology can be used for the photophysical tuning of BODIPY dyes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Thiocyanates / chemical synthesis
  • Thiocyanates / chemistry*

Substances

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