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Issue 29, 2018
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Dynamic diselenide-containing polyesters from alcoholysis/oxidation of γ-butyroselenolactone

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Abstract

A versatile protocol for the synthesis of a variety of multiresponsive diselenide-containing polyesters was investigated. It consists of a one-pot, two-step process with the generation of a selenol by nucleophilic ring opening of γ-butyroselenolactone with a broad range of alcohols in situ, followed by the transformation of the obtained compounds to the corresponding diselenides through a spontaneous oxidative coupling reaction. First, the influence of the catalyst choice, alcohol structure, and solvents on the reaction efficiency was examined. After elaboration of this one-pot reaction, a number of routes, all starting from γ-butyroselenolactone, have been developed for the successful synthesis of linear and crosslinked diselenide-containing polyesters via a mild, straightforward process. The structure of diselenide compounds and polymers was carefully characterized by 1H, 13C, 77Se NMR, FT-IR, HRMS, and SEC. In addition, it has been found that the diselenide-containing polyester networks showed fast reprocessing at a mild temperature (70 °C) or by making use of UV irradiation.

Graphical abstract: Dynamic diselenide-containing polyesters from alcoholysis/oxidation of γ-butyroselenolactone

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Publication details

The article was received on 18 May 2018, accepted on 05 Jul 2018 and first published on 06 Jul 2018


Article type: Paper
DOI: 10.1039/C8PY00736E
Citation: Polym. Chem., 2018,9, 4044-4051

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    Dynamic diselenide-containing polyesters from alcoholysis/oxidation of γ-butyroselenolactone

    C. Wang, X. An, M. Pang, Z. Zhang, X. Zhu, J. Zhu, F. E. Du Prez and X. Pan, Polym. Chem., 2018, 9, 4044
    DOI: 10.1039/C8PY00736E

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