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A Conjugated Figure‐of‐Eight Oligoparaphenylene Nanohoop with Adaptive Cavities Derived from Cyclooctatetrathiophene Core

Lijie Zhan, Chenshu Dai, Guohui Zhang, Jun Zhu, Shaoguang Zhang, Hua Wang, Yi Zeng, Chen‐Ho Tung, Li‐Zhu Wu, Huan Cong

2021Angewandte Chemie International Edition75 citationsDOI

Abstract

Abstract A fully conjugated figure‐of‐eight nanohoop is presented with facile synthesis. The molecule's lemniscular skeleton features the combination of two strained oligoparaphenylene loops and a flexible cyclooctatetrathiophene core. Its rigid yet guest‐adaptive cavities enable the formation of the peanut‐like 1:2 host–guest complexes with C 60 or C 70 , which have been confirmed by X‐ray crystallography and characterized in solution. Further computational studies suggest notable geometric variations and non‐covalent interactions of the cavities upon binding with different fullerenes, as well as overall conjugation comparable to cycloparaphenylenes.

Topics & Concepts

Conjugated systemFullereneCore (optical fiber)MoleculeCovalent bondMaterials scienceCrystallographyChemistryNanotechnologyPolymerOrganic chemistryComposite materialFullerene Chemistry and ApplicationsSynthesis and Properties of Aromatic CompoundsSupramolecular Self-Assembly in Materials
A Conjugated Figure‐of‐Eight Oligoparaphenylene Nanohoop with Adaptive Cavities Derived from Cyclooctatetrathiophene Core | Litcius