Cation recognition on a fullerene-based macrocycle.

Chemical Science
Yoshifumi Hashikawa, Yasujiro Murata

Abstract

Heterocyclic orifices in cage-opened fullerene derivatives are regarded as potential ligands toward metals or ions, being reminiscent of truncated fullerenes as a hypothetical class of macrocycles with spherical π-conjugation. Among a number of cage-opened examples reported thus far, the coordination ability and dynamic behavior in solution still remained unclear due to difficulties in structural determination with multiple coordination sites on the macrocycles. Herein, we present the detailed solution dynamics of a cage-opened C60 derivative bearing a diketo bis(hemiketal) moiety in the presence of alkali metal ions. The NMR spectroscopy disclosed the coordination behavior which is identified as a two-step process with a 1 : 2 stoichiometry. Upon coordination to the Li+ ion, the macrocycle largely varies its properties, i.e., increased absorption coefficients in the visible region due to weakly-allowed charge transfer transitions as well as the inner potential field from neutral to positive by the charge delocalization along with the spherical π-surface. The Li+-complexes formed in situ underwent unprecedented selective dehydroxyhydrogenation under high-pressure conditions. These findings would facilitate further studies on fu...Continue Reading

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Jul 26, 2019·Journal of the American Chemical Society·Yoshifumi Hashikawa, Yasujiro Murata

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Citations

Jul 30, 2021·Journal of the American Chemical Society·Sheng ZhangYasujiro Murata

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Methods Mentioned

BETA
NMR

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