A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene

Dmitrii F. Perepichka, Michael Bendikov, Hong Meng, Fred Wudl

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.

Original languageEnglish
Pages (from-to)10190-10191
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number34
DOIs
Publication statusPublished - Aug 27 2003

    Fingerprint

ASJC Scopus subject areas

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

Cite this