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Di-(m-m-m)terphenyl-Embedded Decaphyrin and Its Bis-Rh(I) Complex

  • Mainak Das
    Mainak Das
    School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
    More by Mainak Das
  • B. Adinarayana
    B. Adinarayana
    School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
  • M. Murugavel
    M. Murugavel
    School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
    More by M. Murugavel
  • Subhashree Nayak
    Subhashree Nayak
    School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
  • , and 
  • A. Srinivasan*
    A. Srinivasan
    School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar 752050, Odisha, India
    *E-mail: [email protected]
Cite this: Org. Lett. 2019, 21, 8, 2867–2871
Publication Date (Web):April 8, 2019
https://doi.org/10.1021/acs.orglett.9b00871
Copyright © 2019 American Chemical Society

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    Abstract

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    A new rectangular-shaped carbadecaphyrin was successfully synthesized by introducing a terphenylene unit (m-m-m) in the macrocyclic core. The terphenylene moiety offers an open framework with multiple binding pockets to stabilize two Rh(I) ions in the core. The photophysical and structural studies reveal the non-aromatic character of the ligand and its bis-Rh(I) complex.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b00871.

    • Additional details about experimental methods, the synthetic procedure and spectral characterization, mass and NMR spectral analyses, and single-crystal X-ray analyses of 4 and 5 (PDF)

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    CCDC 18956321895633 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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    Cited By

    This article is cited by 13 publications.

    1. Sangya Chitranshi, B. Adinarayana, Mainak Das, Sebastian Anila, Cherumuttathu H. Suresh, A. Srinivasan. Rh(I) and Organo-Rh(III) Complexes of meso-Triarylbiphenylcorrole. Inorganic Chemistry 2023, 62 (1) , 336-341. https://doi.org/10.1021/acs.inorgchem.2c03401
    2. Damaris Waiyigo Thuita, Christian Brückner. Metal Complexes of Porphyrinoids Containing Nonpyrrolic Heterocycles. Chemical Reviews 2022, 122 (9) , 7990-8052. https://doi.org/10.1021/acs.chemrev.1c00694
    3. Yunchao Zheng, Xue Wang, Hao Chen, Tian Lu, Zhiming Duan, Chuanhu Lei. 1,4-Phenylene-Incorporated Decaphyrin(1.0.1.0.0.1.0.1.0.0): Synthesis, Structure, and Topological Chirality. Organic Letters 2022, 24 (13) , 2509-2514. https://doi.org/10.1021/acs.orglett.2c00636
    4. 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
    5. Thondikkal Sulfikarali, Jayaprakash Ajay, Cherumuttathu H. Suresh, Padinjare V. Bijina, Sabapathi Gokulnath. Synthesis, Structure, and Optical Properties of Di-m-benzihexaphyrins (1.1.0.0.0.0) and Di-m-benziheptaphyrins (1.0.1.0.0.0.0): Blackening of m-Phenylene-Linked Dicarbaporphyrinoids by Simple π-Expansion. The Journal of Organic Chemistry 2020, 85 (12) , 8021-8028. https://doi.org/10.1021/acs.joc.0c00754
    6. Sangya Chitranshi, Mainak Das, B. Adinarayana, Won-Young Cha, Dongho Kim, A. Srinivasan. Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0). Organic Letters 2020, 22 (3) , 1081-1085. https://doi.org/10.1021/acs.orglett.9b04614
    7. Bharti Yadav, Nisha Rawat, Mangalampalli Ravikanth. Synthesis and Studies of Di( p ‐Benzi)Decaphyrin and Di(9,10‐Anthracenyl)Decaphyrin. Chemistry – An Asian Journal 2022, 17 (24) https://doi.org/10.1002/asia.202200943
    8. 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
    9. Weinan Zhou, Mengdi Hao, Tian Lu, Zhiming Duan, Tridib Sarma, Jonathan L. Sessler, Chuanhu Lei. Carbazole‐Containing Carbadecaphyrins: Non‐aromatic Expanded Porphyrins that Undergo Proton‐Triggered Conformational Changes. Chemistry – A European Journal 2021, 27 (65) , 16173-16180. https://doi.org/10.1002/chem.202102939
    10. 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
    11. Bartosz Szyszko, Lechosław Latos‐Grażyński. Expandierte Carbaporphyrinoide. Angewandte Chemie 2020, 132 (39) , 17020-17049. https://doi.org/10.1002/ange.201914840
    12. Bartosz Szyszko, Lechosław Latos‐Grażyński. Expanded Carbaporphyrinoids. Angewandte Chemie International Edition 2020, 59 (39) , 16874-16901. https://doi.org/10.1002/anie.201914840
    13. Mainak Das, Sangya Chitranshi, M. Murugavel, B. Adinarayana, Cherumuttathu H. Suresh, A. Srinivasan. Isosmaragdyrin with an N 3 C 2 core: stabilization of Rh( i ) and organo-Pt( ii ) complexes. Chemical Communications 2020, 56 (24) , 3551-3554. https://doi.org/10.1039/D0CC00214C

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