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Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)

  • Sangya Chitranshi
    Sangya Chitranshi
    National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
  • Mainak Das
    Mainak Das
    National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
    More by Mainak Das
  • B. Adinarayana
    B. Adinarayana
    National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
  • Won-Young Cha
    Won-Young Cha
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
    Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea
  • Dongho Kim
    Dongho Kim
    Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea
    More by Dongho Kim
  • , and 
  • A. Srinivasan*
    A. Srinivasan
    National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
    *E-mail: [email protected]. Telephone: +91-674-2494170.
Cite this: Org. Lett. 2020, 22, 3, 1081–1085
Publication Date (Web):January 14, 2020
https://doi.org/10.1021/acs.orglett.9b04614
Copyright © 2020 American Chemical Society

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    Abstract

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    An o-p-biphenyl moiety-incorporated 32π hexaphyrin(3.1.1.3.1.1) is successfully achieved. Replacing ortho with meta connectivity in the biphenyl unit of hexaphyrin leads to the formation of its structural isomer, octaphyrin(1.1.1.0.1.1.1.0). Spectral and structural analyses reveal the lack of planarity in hexaphyrin and the presence of an m-arene unit in octaphyrin, thus affording nonaromatic characteristics.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.9b04614.

    • Synthetic procedures and spectral data for 4–11 (PDF)

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    CCDC 19727881972790 contain 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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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 7 publications.

    1. Mainak Das, B. Adinarayana, A. Srinivasan. Recent Advances in the Design and Syntheses of Porphyrinoids by Embedding Higher Analogues of Arene and Pyridine Units. ACS Omega 2021, 6 (51) , 35204-35212. https://doi.org/10.1021/acsomega.1c05444
    2. Bartosz Szyszko. Phenanthrene‐Embedded Carbaporphyrinoids and Related Systems: From Ligands to Cages and Molecular Switches. European Journal of Organic Chemistry 2022, 2022 (30) https://doi.org/10.1002/ejoc.202200714
    3. Bharti Yadav, Mangalampalli Ravikanth. Synthesis and Studies of Structural Isomers of meso ‐Fused Dicarbahexaphyrins. Chemistry – An Asian Journal 2022, 17 (14) https://doi.org/10.1002/asia.202200432
    4. Weinan Zhou, Tridib Sarma, Yonghuan Su, Chuanhu Lei, Jonathan L. Sessler. Kinetic trapping of a cobalt( ii ) metallocage using a carbazole-containing expanded carbaporphyrinoid ligand. Chemical Science 2022, 13 (3) , 692-697. https://doi.org/10.1039/D1SC06514A
    5. Bartosz Szyszko, Paweł Rymut, Maksym Matviyishyn, Agata Białońska, Lechosław Latos‐Grażyński. Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1). Angewandte Chemie International Edition 2020, 59 (45) , 20137-20146. https://doi.org/10.1002/anie.202008518
    6. Bartosz Szyszko, Paweł Rymut, Maksym Matviyishyn, Agata Białońska, Lechosław Latos‐Grażyński. Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1). Angewandte Chemie 2020, 132 (45) , 20312-20321. https://doi.org/10.1002/ange.202008518
    7. M. Murugavel, B. Adinarayana, Mainak Das, S. Peruncheralathan, Narasinga Rao Palepu, A. Srinivasan. PtCl 2 mediated peripheral transformation of carbatriphyrin(3.1.1) into a meso -fused β–β′ dimer and its monomer analogue. Chemical Communications 2020, 56 (84) , 12809-12812. https://doi.org/10.1039/D0CC05309K

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