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Updated: Mar 16, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Redox-Dependent Transformation of a Hydrazinobuckybowl between Curved and Planar Geometries
Shuhei Higashibayashi1, Palash Pandit2, Rie Haruki3
1Institute for Molecular Science, Myodaiji, Okazaki, 444-8787, Japan. higashi@ims.ac.jp.
Abstract:
A red-fluorescent heterobuckybowl with an embedded hydrazine structure was synthesized from a cyclobiphenothiazine derivative via a strained cyclobicarbazole. The hydrazinobuckybowl was found to possess bowl and twist structures in the neutral state, a shallow bowl structure in the monocation state, and a planar structure in the dication state by means of X-ray crystallographic analysis, DFT calculations, and a comparison of experimental and calculated (13) C NMR chemical shifts. The hydrazinobuckybowl is the first buckybowl that changes its geometry between curved bowl/twist structures and a planar structure depending on the oxidation state. The drastic geometrical change was possible as a result of the presence of two heteroatoms in the bowl skeleton and the multiple reversible redox reactions of the compound. Owing to the two kinds of bowl and twist conformations, the bowl-inversion dynamics of the hydrazinobuckybowl were found to follow a triple-well potential model.
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