Synthesis, structure, and isomerization of decapentynylcorannulene: Enediyne cyclization/lnterconversion of C40R10 isomers

Tomoharu Hayama, Yao Ting Wu, Anthony Linden, Kim K. Baldridge, Jay S. Siegel

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Decapentynylcorannulene (5) is prepared via aryl-alkyne coupling chemistry of decachlorocorannulene and trimethylstannylpentyne. The crystal structure of 5 is compared with the ab initio computed structure of decaethynylcorannulene (3). The relative structure and energetics of 3 and its carbon nanotube isomer C40H10 (2) are discussed. Per-alkynyl-polynuclear aromatic hydrocarbons, such as 3, constitute a high energy form of carbon-rich compounds. During the synthesis of 3, enediyne cyclization forms the diradical, which ring-opens to the biscumulenyl [10]annulene (6). Discovery of this process supports the idea that derivatives of 2 could result from corresponding derivatives of 3 through electrocyclic mechanisms and demonstrates a new carbon skeletal rearrangement for strained polynuclear aromatic networks. Derivatives of 3, like 5, warrant further investigation to find viable precursors for monodispersed single-walled carbon-based nanotubes.

Original languageEnglish
Pages (from-to)12612-12613
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number42
DOIs
Publication statusPublished - 2007 Oct 24

All Science Journal Classification (ASJC) codes

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

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