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Issue 22, 2018
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Curved π-conjugated corannulene dimer diradicaloids

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Abstract

So far, most reported open-shell singlet diradicaloids are based on planar π-conjugated molecules. Herein, we report the bridged corannulene dimer diradicaloids, Cor-D1 and Cor-D2, both showing a three-dimensional curved π-conjugated structure. Cor-D1 has a small diradical character (y0 = 5.4%) and behaves more like a closed-shell quinoidal compound at room temperature, while Cor-D2 is a typical open-shell diradicaloid with a larger diradical character (y0 = 16.9%). Both compounds exhibited paramagnetic activity at elevated temperatures, with a singlet–triplet energy gap (ΔES–T) of −8.4 and −3.0 kcal mol−1, respectively. X-ray crystallographic analysis revealed that both molecules have a dumbbell-shaped geometry, with the two terminal corannulene bowls bent to opposite directions. The spin is largely delocalized onto the two bowls in Cor-D2 and there are multiple [CH⋯π] interactions between the neighboring bowls. Chemical oxidation/reduction to their respective dications/dianions results in global aromaticity with [4n + 2] π-electrons delocalized through the periphery of the whole framework.

Graphical abstract: Curved π-conjugated corannulene dimer diradicaloids

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Publication details

The article was received on 26 Mar 2018, accepted on 12 May 2018 and first published on 16 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01388H
Citation: Chem. Sci., 2018,9, 5100-5105
  • Open access: Creative Commons BY license
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    Curved π-conjugated corannulene dimer diradicaloids

    Q. Wang, P. Hu, T. Tanaka, T. Y. Gopalakrishna, T. S. Herng, H. Phan, W. Zeng, J. Ding, A. Osuka, C. Chi, J. Siegel and J. Wu, Chem. Sci., 2018, 9, 5100
    DOI: 10.1039/C8SC01388H

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