Synthesis, structure, and properties of extended π-conjugated systems bearing sterically crowded triarylphosphines

Shigeru Sasaki, Kohji Sasaki, Masaaki Yoshifuji

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The sterically crowded triarylphosphines bearing formyl and benzoyl groups were synthesized and characterized by X-ray crystallography. The benzoyl derivative was converted to the p-quinomethane conjugated with the triarylphosphine. The McMurry coupling of the formyl derivative afforded the diarylethene bearing the two sterically-crowded-triarylphosphine moieties. The cyclic voltammograms of these compounds show reversible redox waves corresponding to the oxidation to the radical cations of the triarylphosphines and irreversible or quasi-reversible waves corresponding to the reduction of the acceptor moieties. The electronic and the fluorescence spectra of these π-conjugated systems, especially push-pull substituted derivatives, exhibit bathochromic shift typical of the extended π-conjugated systems especially in the polar solvent, and the large Stokes shift typical of the crowded triarylphosphines is enhanced by conjugation with the acceptor moiety.

Original languageEnglish
Pages (from-to)3307-3315
Number of pages9
JournalJournal of Organometallic Chemistry
Volume696
Issue number21
DOIs
Publication statusPublished - 2011 Oct 15

Keywords

  • Electronic spectrum
  • Phosphine
  • Redox properties
  • π-Conjugated system

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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