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Cyclooctatetraene‐Embedded Carbon Nanorings

Sheng‐Nan Lei, Ling Zhu, Ning Xue, Xuedong Xiao, Le Shi, Duan‐Chao Wang, Zhe Liu, Xin‐Ru Guan, Yuan Xie, Ke Liu, Lianrui Hu, Zhaohui Wang, J. Fraser Stoddart, Qing‐Hui Guo

2024Angewandte Chemie International Edition13 citationsDOIOpen Access PDF

Abstract

Abstract With the prosperity of the development of carbon nanorings, certain topologically or functionally unique units‐embedded carbon nanorings have sprung up in the past decade. Herein, we report the facile and efficient synthesis of three cyclooctatetraene‐embedded carbon nanorings ( COTCNR s) that contain three ( COTCNR1 and COTCNR2 ) and four ( COTCNR3 ) COT units in a one‐pot Yamamoto coupling. These nanorings feature hoop‐shaped segments of Gyroid (G‐), Diamond (D‐), and Primitive (P‐) type carbon schwarzites. The conformations of the trimeric nanorings COTCNR1 and COTCNR2 are shape‐persistent, whereas the tetrameric COTCNR3 possesses a flexible carbon skeleton which undergoes conformational changes upon forming host–guest complexes with fullerenes ( C 60 and C 70 ), whose co‐crystals may potentially serve as fullerene‐based semiconducting supramolecular wires with electrical conductivities on the order of 10 −7 S cm −1 (for C 60 ⊂ COTCNR3 ) and 10 −8 S cm −1 (for C 70 ⊂ COTCNR3 ) under ambient conditions. This research not only describes highly efficient one‐step syntheses of three cyclooctatetraene‐embedded carbon nanorings which feature hoop‐shaped segments of distinctive topological carbon schwarzites, but also demonstrates the potential application in electronics of the one‐dimensional fullerene arrays secured by COTCNR3 .

Topics & Concepts

CyclooctatetraeneCarbon fibersFullereneSupramolecular chemistryMaterials scienceNanotechnologyCrystallographyChemistryCrystal structureMoleculeComposite materialOrganic chemistryComposite numberGraphene research and applicationsFullerene Chemistry and ApplicationsSynthesis and Properties of Aromatic Compounds