Synthesis and properties of novel fluorescent switches

J Org Chem. 2005 Jul 8;70(14):5545-9. doi: 10.1021/jo050540k.

Abstract

[reaction: see text] Photochromic dithienylethene moieties were covalently attached to fluorescent 4,4-difluoro-8-(4'-iodophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (iodo-BODIPY) via a phenylacetylene linker. UV light induced isomerization of the photochrome results in significant decrease in fluorescence intensity. This fluorescence can be recovered with visible light. Steady-state fluorescence measurements demonstrate that the emission of the dye can be modulated by external light. An intramolecular energy transfer mechanism accounts for the fluorescence quenching in the UV light produced isomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives
  • Acetylene / chemistry
  • Boron Compounds / chemical synthesis*
  • Ethylenes / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Isomerism
  • Light
  • Molecular Structure
  • Spectrometry, Fluorescence

Substances

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