Photophysical study of new versatile multichromophoric diads and triads with BODIPY and polyphenylene groups

J Phys Chem A. 2008 Oct 30;112(43):10816-22. doi: 10.1021/jp8051592. Epub 2008 Oct 4.

Abstract

The photophysical properties of multichromophoric dyes with borondipyrromethene (BODIPY) and poly- p-phenylene (di- p-phenylene and tri- p-phenylene) groups in the same molecule are studied in detail. The excitation of the polyphenylene moiety in the UV region leads to a strong visible fluorescent emission of the BODIPY chromophore, via intramolecular excitation energy transfer between both groups. Consequently, these multichromophoric dyes are characterized by a large "virtual" Stokes shift, with a high fluorescence capacity and an efficient laser emission. On the other hand, the photophysical properties of a related dichromophoric dye with a hydroxy end group at the di- p-phenylene moiety show an important decrease in the fluorescent emission due to a photoinduced electron transfer process in basic media. Therefore, its photophysical properties are sensitive to the environmental acidity/basicity and could be applied as a proton sensor.

MeSH terms

  • Boron Compounds / chemistry*
  • Computer Simulation
  • Cycloparaffins / chemistry*
  • Energy Transfer
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Models, Chemical
  • Molecular Structure
  • Photochemistry
  • Quantum Theory

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Cycloparaffins
  • Fluorescent Dyes
  • poly-para-phenylene