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; Lian-Rui Hu; Zhaohui Wang; J Fraser Stoddart; Qing-Hui Guo

doi:10.1002/anie.202402255

Cyclooctatetraene-Embedded Carbon Nanorings

Angew Chem Int Ed Engl. 2024 Mar 29:e202402255. doi: 10.1002/anie.202402255. Online ahead of print.

Authors

Sheng-Nan Lei^{1

2}, Ling Zhu³, Ning Xue⁴, 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 Hu³, Zhaohui Wang⁴, J Fraser Stoddart^{1

5

6

7}, Qing-Hui Guo^{1

2

8}

Affiliations

¹ Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
² ZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou, 311215, China.
³ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.
⁴ Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China.
⁵ Chong Yuet Ming Chemistry Building, The University of Hong Kong, Hong Kong SAR.
⁶ Simpson Querrey Institute for BioNanotechnology, 303 East Superior Street, Chicago, IL-60611, USA.
⁷ School of Chemistry, University of New South Wales, Sydney, NSW-2052, Australia.
⁸ MOE Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084, China.

PMID: 38551062
DOI: 10.1002/anie.202402255

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.

Abstract

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