Synthesis, electronic properties, and reactivity of phospholes and 1,1/-biphospholes bearing 2-or 3-thienyl C-substituents

Omrane Fadhel, Dénes Szieberth, Valérie Deborde, Christophe Lescop, László Nyulászi, Muriel Hissler, Régis Réau

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Two series of phospholes and i,i'biphospholes bearing either 2-or 3-thienyl substituents at the C atoms are prepared by using the Fagan-Nugent route. Their optical (UV/Vis absorption, fluorescence spectra) and electrochemical properties are systematically evaluated. Of particular interest, the first ever reported 3-thienyl-substituted phospholes exhibit higher LUMO levels than their 2-thienyl analogues, and show accordingly different physical properties. This study also re-veals that the i,i'-biphospholes exhibit a-Jt conjugation. The phosphole and i,i '-biphosphole derivatives bearing 3-thienyl substituents are characterized by X-ray diffraction study. The structure-property relationship established following the experimental data are fully supported by theoretical studies including time-dependent(TD)-DF1 spectra. A photocyclization reactioi performed on the thioxo-and oxo phospholes having 3-thienyl substitu ents affords a novel ring-fused phosp hole-thiophene derivative, which wa characterized by an X-ray diffractio study. The structure and electroni properties of this novel dithienophos phole are discussed based on experi mental and theoretical data.

Original languageEnglish
Pages (from-to)4914-4924
Number of pages11
JournalChemistry - A European Journal
Volume15
Issue number19
DOIs
Publication statusPublished - May 4 2009

Keywords

  • Densit functional calculations
  • Phospholes
  • Photocyclization
  • Pi interactions
  • Thiophenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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