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Issue 6, 2017
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Electronic and crystal structures of 1,2,3-triazole-fused p-benzoquinone derivatives

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The preparation and crystal structure analyses of 1,2,3-triazole fused p-benzoquinone derivatives were performed conventionally from electronically active tetraamino-p-benzoquinone (1). The redox behaviour and crystal structure of 1 were compared with those of chemically stable strong electron donor tetrakis(dimethylamino)-p-benzoquinone (3). The reaction of 1 with NaNO2 generated a diazonium salt, which reacted further to give residual amino groups of 1, forming bis(1,2,3-triazole)-p-benzoquinone (2) in high yield. Along with intramolecularly cyclized compound 2, novel π-extended dimeric product bis(1,2,3-triazole)-phenazinetetraone (4) was also generated in this reaction and isolated in charge-transfer complexes with perylene and coronene. The molecular structures of neutral 2, monoanionic 2, and dianionic 22 were confirmed by single crystal X-ray structural analyses, where the acidic protons in 2 existed in the 2-position of the 1,2,3-triazole unit, whereas one proton in 2 was localized at the 1-position of the 1,2,3-triazole unit. The electron accepting ability of bis(1,2,3-triazole)-p-benzoquinone derivatives decreased in the order 2 > 2 > 22 due to electrostatic repulsive interactions in the anion radical and dianion state. Hydrogen-bonded new electron acceptor 4 was surrounded by four H2O molecules in the crystalline state, which formed an alternating donor–acceptor π-stacking interaction.

Graphical abstract: Electronic and crystal structures of 1,2,3-triazole-fused p-benzoquinone derivatives

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The article was received on 13 Oct 2016, accepted on 04 Dec 2016 and first published on 05 Dec 2016

Article type: Paper
DOI: 10.1039/C6CE02167K
Citation: CrystEngComm, 2017,19, 910-917
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    Electronic and crystal structures of 1,2,3-triazole-fused p-benzoquinone derivatives

    M. Sato, T. Takeda, N. Hoshino and T. Akutagawa, CrystEngComm, 2017, 19, 910
    DOI: 10.1039/C6CE02167K

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