Flattened 1D fragments of fullerene C60 that exhibit robustness toward multi-electron reduction

Masahiro Hayakawa, Naoyuki Sunayama, Shu I. Takagi, Yu Matsuo, Asuka Tamaki, Shigehiro Yamaguchi, Shu Seki and Aiko Fukazawa ()
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Masahiro Hayakawa: Kyoto University
Naoyuki Sunayama: Kyoto University
Shu I. Takagi: Kyoto University
Yu Matsuo: Kyoto University
Asuka Tamaki: Nagoya University
Shigehiro Yamaguchi: Nagoya University
Shu Seki: Kyoto University
Aiko Fukazawa: Kyoto University

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract Fullerenes are compelling molecular materials owing to their exceptional robustness toward multi-electron reduction. Although scientists have attempted to address this feature by synthesizing various fragment molecules, the origin of this electron affinity remains unclear. Several structural factors have been suggested, including high symmetry, pyramidalized carbon atoms, and five-membered ring substructures. To elucidate the role of the five-membered ring substructures without the influence of high symmetry and pyramidalized carbon atoms, we herein report the synthesis and electron-accepting properties of oligo(biindenylidene)s, a flattened one-dimensional fragment of fullerene C60. Electrochemical studies corroborated that oligo(biindenylidene)s can accept electrons up to equal to the number of five-membered rings in their main chains. Moreover, ultraviolet/visible/near-infrared absorption spectroscopy revealed that oligo(biindenylidene)s exhibit enhanced absorption covering the entire visible region relative to C60. These results highlight the significance of the pentagonal substructure for attaining stability toward multi-electron reduction and provide a strategy for the molecular design of electron-accepting π-conjugated hydrocarbons even without electron-withdrawing groups.

Date: 2023
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DOI: 10.1038/s41467-023-38300-3

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