Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Crystallographic Structure Determination of Both [5,6]- and [6,6]-Isomers of Lithium-Ion-Containing Diphenylmethano[60]fullerene

Crystallographic Structure Determination of Both [5,6]- and [6,6]-Isomers of Lithium-Ion-Containing Diphenylmethano[60]fullerene
Yutaka Matsuo, Hiroshi Okada, Hiroki Kawakami, Shinobu Aoyagi
Organic functionalization of lithium-ion-containing [60]fullerene, Li+@C60, was performed by using diphenyl(diazo)methane as a stable, readily available diazo compound to obtain lithium-ion-containing [5,6]- and [6,6]-diphenylmethano[60]fullerenes, Li+@C61Ph2. The bis(trifluoromethanesulfonyl)imide (TFSI) salts of [5,6]- and [6,6]-Li+@C61Ph2 were successfully separated by using a cation exchange column with eluent containing LiTFSI. Improved separation protocol and high crystallinity of ionic components in less polar solvents enabled separate crystallization of each isomer. Both [5,6]-open and [6,6]-closed structures of Li+@C61Ph2 were determined by synchrotron radiation X-ray crystallography. Elucidating the [5,6]-open methano[60]fullerene (fulleroid) structure will contribute to materials research on fulleroids.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00730

DOI: 10.1021/acs.joc.7b00730

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