Jump to main content
Jump to site search

Issue 6, 2017
Previous Article Next Article

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

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Publication details

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
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements