3 years ago

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

Synthesis and Crystal Structure of Li+@Fluoreno[60]fullerene: Effect of Encapsulated Lithium Ion on Electrochemistry of Spiroannelated Fullerene
Hiroshi Okada, Hiroshi Ueno, Shinobu Aoyagi, Yutaka Matsuo
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01893

DOI: 10.1021/acs.joc.7b01893

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