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Infinitene: A Helically Twisted Figure-Eight [12]Circulene Topoisomer
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    Infinitene: A Helically Twisted Figure-Eight [12]Circulene Topoisomer
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 2, 862–871
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    https://doi.org/10.1021/jacs.1c10807
    Published December 15, 2021
    Copyright © 2021 American Chemical Society

    Abstract

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    New forms of molecular nanocarbon particularly looped polyarenes adopting various topologies contribute to the fundamental science and practical applications. Here we report the synthesis of an infinity-shaped polyarene, infinitene (1) (cyclo[c.c.c.c.c.c.e.e.e.e.e.e]dodecakisbenzene), comprising consecutively fused 12-benzene rings forming an enclosed loop with a strain energy of 60.2 kcal·mol–1. Infinitene (1) represents a topoisomer of still-hypothetical [12]circulene, and its scaffold can be formally visualized as the outcome of the “stitching” of two homochiral [6]helicene subunits by both their ends. The synthetic strategy encompasses transformation of a rationally designed dithiacyclophane to cyclophadiene through the Stevens rearrangement and pyrolysis of the corresponding S,S′-bis(oxide) followed by the photocyclization. The structure of 1 is a unique hybrid of helicene and circulene with a molecular formula of C48H24, which can be regarded as an isomer for kekulene, [6,6]carbon nanobelt ([6,6]CNB), and [12]cyclacene. Infinitene (1) is a bench-stable yellow solid with green fluorescence and soluble to common organic solvents. Its figure-eight molecular structure was unambiguously confirmed by X-ray crystallography. The scaffold of 1 is significantly compressed as manifested by a remarkably shortened distance (3.152–3.192 Å) between the centroids of two π–π stacked central benzene rings and the closest C···C distance of 2.920 Å. Fundamental photophysical properties of 1 were thoroughly elucidated by UV–vis absorption and fluorescence spectroscopic studies and density functional theory calculations. Its configurational stability enabled separation of the corresponding enantiomers (P,P) and (M,M) by a chiral HPLC. Circular dichroism (CD) and circularly polarized luminescence (CPL) measurements revealed that 1 has moderate |gCD| and |gCPL| values.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.1c10807.

    • Experimental procedures, 1H and 13C NMR spectra, characterization data for all new compounds, optical properties, computational data, and crystallographic data of 1 (PDF)

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    CCDC 2113525 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336033.

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    Cited By

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    This article is cited by 53 publications.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 2, 862–871
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.1c10807
    Published December 15, 2021
    Copyright © 2021 American Chemical Society

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