Organophosphorus π-conjugated systems
for opto-electronic applications

We are developing the use of phosphole (1) for the tailoring of π-conjugated materials since this heterocycle possesses unique properties compared to its widely used thiophene or pyrrole analogues. Due to its low aromatic character and reactive P-atom, a variety of conjugated systems with different structures and electronic properties can be readily prepared. These results show the high potential of organophosphorus derivatives for the tailoring of π-conjugated materials toward optoelectronic applications.

Collaborations

Dr J. Rault-Berthelot, Université de Rennes I, electropolymerisation

Pr L. Nyulaszi, University of Budapest (Hungary), Dr J.-F. Halet, Université de Rennes I, theoretical calculations

Dr I. Ledoux-Rak, ENS Cachan, NLO measurements

Pr C.-C. Wu, Université de Taiwan (Taiwan), Dr B. Geffroy, Dr N. Lemaitre, CEA Saclay, OLED's manufacturing

Prof. P. Bäuerle, University of Ulm (Germany), new π-conjugated systems

References

• Use of conducting organic poly(phosphole-bithiophene) copolymers for the detection of neutral organophosphorus molecules.
  R. Réau, M. Hissler, C. Odin, J. Rault Berthelot, P. Bauerle, International patent, 2006, WO2006/122909.

• Phosphole-modified Poly(thiophenes) : Unique Postfunctionalizable Conjugated Polymers That Sense Elemental Chalcogenides.
  M. Sebastian, M. Hissler, C. Fave, J. Rault-Berthelot, C. Odin, R. Réau, Angew. Chem. Int. Ed., 2006, 45, 6152.

• Toward Functional π-Conjugated Organophosphorus Materials : Design of Phosphole-based Oligomers for Electroluminescent Devices.
  H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, R. Réau, J. Am. Chem. Soc., 2006, 128, 983.

• A Study of Mono- and 1,1'-Di-Phosphaferrocenes as Building Blocks for π-Conjugated Systems.
  L. Zhang, M. Hissler, H.-B. Bu, P. Bäuerle, C. Lescop, R Réau, Organometallics, 2005, 24, 5369.

• The rise of organophosphorus derivatives in π-conjugated material chemistry.
  M. Hissler, P. W. Dyer, R. Réau, Topics in Current Chemistry New Aspects in Phosphorus Chemistry V, Springer, 2005.

• Connecting π-Chromophores by σ-P-P bond : New Type of Assemblies Exhibiting σ-π Conjugation.
  C. Fave, M. Hissler, T. Kárpáti, J. Rault-Berthelot, V. Deborde, L. Toupet, L. Nyulászi, R. Réau, J. Am. Chem. Soc., 2004, 136, 6058.

• Synthesis and electronic properties of alternating α,α'-thiophene-phosphole oligomers.
  C. Hay, C. Fave, M. Hissler, J. Rault-Berthelot, R. Réau, Org. Lett., 2003, 19, 3467.

• The First Examples of Organophosphorus-Containing Materials for Light-Emitting Diodes.
  C. Fave, T-Y. Cho, M. Hissler, C.-W. Chen, T.-Y. Luh, C.-C. Wu, R. Réau, J. Am. Chem. Soc., 2003, 125, 9254.

• Ligand trans-effect : using an old concept as a novel approach to bis(dipolar) NLO-phores.
  C. Fave, M. Hissler, K. Sénéchal, I. Ledoux, J. Zyss, R. Réau, Chem. Commun., 2002, 1674.

• Phosphole-Containing π-Conjugated Systems : from Model Molecules to Polymer Films on Electrodes.
  C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulaszi, R. Réau, Chem. Eur. J., 2001, 7, 4222.