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Chemical properties and self-assembled-ordered structures of π-conjugated cooligomers consisted of 2,6-dialkoxynaphthalene-1,5-diyl, 2,1,3-benzothiadiazole-4,7-diyl, and 1,4-phenylenediethynylene units

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Abstract

π-Conjugated cooligomers consisted of 2,6-dialkoxynaphthalene-1,5-diyl (RNap), 2,1,3-benzothiadiazole-4,7-diyl, and 1,4-phenylenediethynylene units were synthesized by Pd-complex-catalyzed condensation reactions. The UV–Vis, photoluminescence, and powder X-ray diffraction measurements suggested that the oligomers have self-assembling-ordered structures in the solid state. The ordered structures depended on the distance between the RNap units of the oligomers. The oligomers underwent electrochemical oxidation (p-doping), which occurred at lower potentials for films than for acetonitrile solutions containing [Et4N]BF4. This effect is caused by the longer π-conjugation lengths of the oligomers in films, which was attributed to molecular self-assembly leading to ordered structures in the solid state.

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Authors and Affiliations

  1. Department of Chemistry, Interdisciplinary Graduate School of Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue, 690-8504, Japan

    Isao Yamaguchi & Asami Kondo

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  1. Isao Yamaguchi
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  2. Asami Kondo
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Correspondence to Isao Yamaguchi.

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Yamaguchi, I., Kondo, A. Chemical properties and self-assembled-ordered structures of π-conjugated cooligomers consisted of 2,6-dialkoxynaphthalene-1,5-diyl, 2,1,3-benzothiadiazole-4,7-diyl, and 1,4-phenylenediethynylene units. Polym. Bull. 75, 1635–1650 (2018). https://doi.org/10.1007/s00289-017-2117-9

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  • DOI: https://doi.org/10.1007/s00289-017-2117-9

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