Bis-4,4′-biphenyl Ring Embedded Octaphyrin with Three Distinct Conformational Structures

Sangya Chitranshi, B. Adinarayana, Mainak Das, Won Young Cha, Dongho Kim, A. Srinivasan

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


Three distinct conformational structures of carbaoctaphyrins were prepared by incorporating bis-4,4'-biphenyl units in the macrocyclic core. The free-base form adopts a figure-eight conformation, whereas the protonation triggers a conformational change with a pyrrole ring inversion and acquires an open-framework structure. The insertion of bis-RhI metal ion in the macrocyclic core affords a singly twisted conformational structure. Furthermore, the local aromaticity in the bis-4,4'-biphenyl ring dominates the overall macrocyclic aromaticity in all three forms, and thus adopts nonaromatic characteristics. These results are supported by spectral as well as theoretical studies, and they are unambiguously confirmed by X-ray crystal analyses.

Original languageEnglish
Pages (from-to)12911-12915
Number of pages5
JournalChemistry - A European Journal
Issue number56
Publication statusPublished - 2019 Oct 8

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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