Connecting π-Chromophores by σ-P-P Bonds: New Type of Assemblies Exhibiting σ-π-Conjugation

Claire Fave, Muriel Hissler, Tamás Kárpati, Joëlle Rault-Berthelot, Valérie Deborde, Loic Toupet, László Nyulászi, Régis Réau

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Abstract

To study the ability of σ-P-P skeleton to mediate interaction between π-chromophores, 1,1′-biphospholes bearing phenyl or thienyl substituents at the 2,2′ and 5,5′-position have been prepared and studied. These air-stable derivatives are readily available via a "one-pot" synthesis starting from diynes. Theoretical studies and UV-vis data clearly establish that the two π-systems interact via the σ-P-P bridge. This through-bond interaction results in a lowering of the optical HOMO-LUMO gap of the assemblies. The nucleophilic σ3-P centers of these 1,1′-biphospholes allow chemical modifications of the σ-bridge. These modifications offer further tuning of the optical properties of the assembly. Electrooxidation of the thienyl-substituted 1,1′-biphosphole results in electroactive materials characterized by low optical band gap and reversible p-doping.

Original languageEnglish
Pages (from-to)6058-6063
Number of pages6
JournalJournal of the American Chemical Society
Volume126
Issue number19
DOIs
Publication statusPublished - May 19 2004

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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