Tetrakis(phenylethynyl)tetracene: A New π-Extended Rubrene Derivative

Kei Kitamura, Kenta Asahina, Yusaku Nagai, Haruki Sugiyama, Hidehiro Uekusa, Toshiyuki Hamura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

An efficient synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, new π-extended rubrene derivatives, was developed by means of [2+4] cycloaddition of dialkynylnaphthalyne and dialkynylisobenzofuran. Importantly, two alkynyl groups introduced into the aryne exerts a significant effect in lowering the LUMO energy, allowing practical access to sterically overcrowded polycyclic structures through an efficient HOMO–LUMO interaction. Study on the potential reactivity inherent in the peri-ethynyl-substituted tetracenes revealed several interesting reactivities. X-ray analysis of these new π-extended derivatives showed distorted structures to reduce steric repulsion due to the existence of the substituents at the peri-positions.

Original languageEnglish
Pages (from-to)14034-14038
Number of pages5
JournalChemistry - A European Journal
Volume24
Issue number53
DOIs
Publication statusPublished - 2018 Sep 20
Externally publishedYes

Keywords

  • crowded tetracene
  • cycloaddition
  • dialkynylisobenzofuran
  • naphthalyne
  • polycycles
  • rubrene

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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