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Issue 39, 2018
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Rational synthesis of benzimidazole[3]arenes by CuII-catalyzed post-macrocyclization transformation

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Abstract

A new series of calix[n]arene analogues, benzimidazole[3]arenes, was rationally synthesized by CuII-catalyzed post-macrocyclization transformation of a tris(o-phenylenediamine) macrocycle, and fully characterized by NMR, MS, and single-crystal X-ray diffraction (XRD) analyses. The resulting syn- and anti-benzimidazole[3]arenes have a bowl-shaped and a warped structure, respectively, in their crystalline states, and both display a dynamic inversion behavior in solution. This modification resulted in strong fluorescence due to the generated benzimidazole moieties. The mechanistic study of the post-macrocyclization transformation demonstrated that the formation of both benzimidazole[3]arenes was catalyzed, via triimine intermediates, by CuII ions in air through oxidation and cyclization of the tris(o-phenylenediamine) macrocycle.

Graphical abstract: Rational synthesis of benzimidazole[3]arenes by CuII-catalyzed post-macrocyclization transformation

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Publication details

The article was received on 12 Jul 2018, accepted on 05 Sep 2018 and first published on 05 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03086C
Citation: Chem. Sci., 2018,9, 7614-7619
  • Open access: Creative Commons BY license
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    Rational synthesis of benzimidazole[3]arenes by CuII-catalyzed post-macrocyclization transformation

    S. Tashiro, T. Umeki, R. Kubota and M. Shionoya, Chem. Sci., 2018, 9, 7614
    DOI: 10.1039/C8SC03086C

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