Highly coplanar very long oligo(alkylfuran)s: A conjugated system with specific head-to-head defect

Xu Hui Jin, Dennis Sheberla, Linda J.W. Shimon, Michael Bendikov

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Well-defined monodisperse conjugated oligomers, which have planar backbones and are free from the disturbance of substituents, attract broad interest. Herein, we report a series of symmetrical, isomerically pure oligofurans, namely, the 16-mer 16F-6C6 together with the related nF-2C 6 (n = 4, 6, 8). Through computational studies and detailed spectroscopic and X-ray characterization, for the first time, we show that the planarity of the furan backbone is almost unaffected by the head-to-head defect which is known to cause considerable twists in its oligo- or polythiophene analogues. We present that the properties of these rigid oligo(alkylfuran)s are strongly influenced by the conjugation length. As the longest monodisperse α-oligofuran synthesized to date, 16F-6C6 was observed to be stable and highly fluorescent. Experimental and computational studies of the redox states of these oligo(alkylfuran)s reveal that 16F-6C6 has singlet biradical (polaron-pair) character in the doubly oxidized ground state: the open-shell singlet (〈S2〉 = 0.989) is 3.8 kcal/mol more stable than the closed-shell dication.

Original languageEnglish
Pages (from-to)2592-2601
Number of pages10
JournalJournal of the American Chemical Society
Volume136
Issue number6
DOIs
Publication statusPublished - Feb 12 2014

ASJC Scopus subject areas

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

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