Synthesis and Crystal Structure of Li+@Fluoreno[60]fullerene: Effect of Encapsulated Lithium Ion on Electrochemistry of Spiroannelated Fullerene

Hiroshi Ueno, Hiroshi Okada, Shinobu Aoyagi, Yutaka Matsuo

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The reaction of [Li+@C60]TFSI- (TFSI = bis(trifluoromethanesulfonyl)imide) with 9-diazofluorene directly produced a [6,6]-adduct of lithium-ion-containing fluoreno[60]fullerene, [6,6]-[Li+@C60(fluoreno)]TFSI-, which was crystallographically characterized. Cyclic voltammetry of the compound showed a reversible one-electron reduction wave at -0.51 V (vs Fc/Fc+) and an irreversible reduction wave for the second electron. The latter was attributed to opening of the three-membered ring due to strong stabilization of the resulting sp3-carbanion by the encapsulated Li+ and formation of a 14π-electron aromatic fluorenyl anion.

Original languageEnglish
Pages (from-to)11631-11635
Number of pages5
JournalJournal of Organic Chemistry
Volume82
Issue number21
DOIs
Publication statusPublished - 2017 Nov 3
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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