Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Yutaka Matsuo, Yun Yu, Xiao Yu Yang, Hiroshi Ueno, Hiroshi Okada, Hiromasa Shibuya, Yeong Suk Choi, Yong Wan Jin

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl anion ArC60-, followed by oxidation using I2 to generate a fullerenyl cation ArC60+, leading to intramolecular demethylative cyclization via fullerene cation-S interaction to the product. Electrochemical and computational studies revealed slightly narrower band gap of this compound than usual fullerene derivatives because of the relatively high-lying HOMO of the fused thieno moiety.

Original languageEnglish
Pages (from-to)6270-6277
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number10
DOIs
Publication statusPublished - 2019 May 17
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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