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Synthesis, Structure, and Reactivity of a Cylinder-Shaped Cyclo[12]orthophenylene[6]ethynylene: Toward the Synthesis of Zigzag Carbon Nanobelts

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Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
JST, ERATO, Itami Molecular Nanocarbon Project, Chikusa, Nagoya 464-8602, Japan
§ Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
Cite this: Org. Lett. 2016, 18, 20, 5352–5355
Publication Date (Web):October 10, 2016
https://doi.org/10.1021/acs.orglett.6b02702
Copyright © 2016 American Chemical Society

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    Abstract

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    Benzannulated cyclacenes (BCs) have been proposed as stable zigzag carbon nanobelts. Density functional theory (DFT) calculations revealed a closed-shell ground state for [12]BC, whereas an open-shell ground state was suggested for [12]cyclacene. The calculated strain energy and frontier molecular orbital energies of [12]BC also implied high stability. An unstrained macrocycle 1, consisting of orthophenylene and ethynylene moieties, was designed as a potential precursor for [12]BC and synthesized by sequential Suzuki–Miyaura cross-coupling of diphenylacetylene derivatives. While the conversion of 1 into [12]BC is still under investigation, an unexpected rearrangement of the triene moieties in 1, affording a tribenzo[f,k,m]tetraphene structure, was discovered during the screening of reaction conditions. An attempt was made to rationalize this result by proposing a plausible reaction mechanism that proceeds via intermediates containing cyclobutadiene or Dewar benzene moieties. The proposed mechanism is partially supported by DFT calculations.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b02702.

    • Experimental details and spectra of new compounds (PDF)

    • X-ray diffraction data for compound 6 (CIF)

    • Cartesian coordinates of optimized structures (XYZ)

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