3D global aromaticity in a fully conjugated diradicaloid cage at different oxidation states

Yong Ni, Tullimilli Y. Gopalakrishna, Hoa Phan, Taeyeon Kim, Tun Seng Herng, Yi Han, Tao Tao, Jun Ding, Dongho Kim, Jishan Wu

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63 Citations (Scopus)


Aromaticity is a vital concept that governs the electronic properties of π-conjugated organic molecules and has long been restricted to 2D systems. The aromaticity in 3D π-conjugated molecules has been rarely studied. Here we report a fully conjugated diradicaloid molecular cage and its global aromaticity at different oxidation states. The neutral compound has an open-shell singlet ground state with a dominant 38π monocyclic conjugation pathway and follows the [4n + 2] Hückel aromaticity rule; the dication has a triplet ground state with a dominant 36π monocyclic conjugation pathway and satisfies [4n] Baird aromaticity; the tetracation is an open-shell singlet with 52 π-electrons that are delocalized along the 3D rigid framework, showing 3D global antiaromaticity; and the hexacation possesses D3 symmetry with 50 globally delocalized π-electrons, showing [6n + 2] 3D global aromaticity. Different types of aromaticity were therefore accessed in one molecular cage platform, depending on the symmetry, number of π-electrons and spin state.

Original languageEnglish
Pages (from-to)242-248
Number of pages7
JournalNature chemistry
Issue number3
Publication statusPublished - 2020 Mar 1

Bibliographical note

Publisher Copyright:
© 2020, The Author(s), under exclusive licence to Springer Nature Limited.

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)


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