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. 2024 May 27;63(22):e202402255.
doi: 10.1002/anie.202402255. Epub 2024 Apr 25.

Cyclooctatetraene-Embedded Carbon Nanorings

Sheng-Nan Lei  1   2 , Ling Zhu  3 , Ning Xue  4 , Xuedong Xiao  1   2 , Le Shi  1   2 , Duan-Chao Wang  1   2 , Zhe Liu  1   2 , Xin-Ru Guan  1   2 , Yuan Xie  1   2 , Ke Liu  1   2 , Lian-Rui Hu  3 , Zhaohui Wang  4 , J Fraser Stoddart  1   5   6   7 , Qing-Hui Guo  1   2   8
Affiliations

Cyclooctatetraene-Embedded Carbon Nanorings

Sheng-Nan Lei et al. Angew Chem Int Ed Engl. .

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 (COTCNRs) 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 (C60 and C70), 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 C60⊂COTCNR3) and 10-8 S cm-1 (for C70⊂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.

Keywords: Carbon schwarzites; Dibenzo[a,e]cyclooctatetraene; Fullerenes supramolecular arrays; Molecular nanocarbons; Molecular nanorings.

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