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Effects of Diphenyl Dichalcogenides on the Radical Polymerization of Diethynyl Disulfide Derivative

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Abstract

Radical reaction of bis(4-prop-2-ynyloxyphenyl) disulfide (1) with 2,2′-azobis(isobutyronitrile) as an initiator provided a polymer with dithioalkene units (2). The 1H and 13C NMR spectra of 2 showed that 2 had mainly E-form dithioalkene structure. The radical reactions of 1 and diphenyl diselenide (3) or diphenyl ditelluride (5) were also carried out. At higher temperature than 70 °C, polymers were obtained with less amount of AIBN than in the case of the homopolymerization of 1. Addition of 3 or 5 in the reaction mixture appeared to promote the radical reaction. Moreover, the obtained structure has high contents of thio-seleno alkene or thio-telluro alkene than expected, which is due to difference of the chalcogen radical reactivity and difference of capture ability of the dichalcogenide.

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Notes

  1. Radical bisthiolation of phenyl 2-propynyl ether with bis(4-methoxyphenyl) disulfide was carried out to assign the peaks of methylene protons. Bisthiolation of them with Pd(PPh3)4 was also carried out to obtain the data that Z -SS shifts upfield after dithiolation. Therefore, the peak at δ 4.45 ppm was assigned to Z -SS and another peak at δ 4.75 ppm was assigned to E -SS.

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Authors and Affiliations

  1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan

    Akiko Nakahashi, Eisuke Miyoshi & Yoshiki Chujo

  2. Department of Chemistry and Materials Technology, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan

    Kensuke Naka

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  1. Akiko Nakahashi
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  2. Eisuke Miyoshi
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  3. Kensuke Naka
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  4. Yoshiki Chujo
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Correspondence to Kensuke Naka or Yoshiki Chujo.

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Nakahashi, A., Miyoshi, E., Naka, K. et al. Effects of Diphenyl Dichalcogenides on the Radical Polymerization of Diethynyl Disulfide Derivative. J Inorg Organomet Polym 19, 55–66 (2009). https://doi.org/10.1007/s10904-008-9248-2

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  • DOI: https://doi.org/10.1007/s10904-008-9248-2

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