Phosphole-containing π-conjugated systems: From model molecules to polymer films on electrodes

Caroline Hay, Muriel Hissler, Cédric Fischmeister, Joëlle Rault-Berthelot, Loïc Toupet, László Nyulászi, Régis Réau

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233 Citations (Scopus)

Abstract

Two series of 2,5-dipyridyland 2,5-dithienylphosphole derivatives containing σ3- or σ4-P atoms were prepared, and their optical (UV/Vis absorption, fluorescence spectra) and electrochemical properties were systematically evaluated. These physical properties depend mainly on the natures of the 2,5-substituents and of the phosphorus moiety, and they revealed that these compounds contain extended π-conjugated systems. Structure- property relationships were established on the basis of these experimental data and ab initio calculations on the parent molecules. The limited aromatic character and low-lying LUMO of the phosphole ring appear to be crucial for achieving a highly delocalised π system. Electrooxidation of 2,5-dithienylphosphole derivatives affords electroactive films with low optical band gaps. As observed for the corresponding monomers, the optical and electrochemical properties of the polymers can be varied over a wide range by modifying the nature of the phosphorus moiety.

Original languageEnglish
Pages (from-to)4222-4236
Number of pages15
JournalChemistry - A European Journal
Volume7
Issue number19
DOIs
Publication statusPublished - Oct 1 2001

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Keywords

  • Ab initio calculations
  • Electrochemistry
  • Phosphorus heterocycles
  • Pi interactions
  • Thin films

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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