TY - JOUR
T1 - Dynamic diselenide-containing polyesters from alcoholysis/oxidation of γ-butyroselenolactone
AU - Wang, Can
AU - An, Xiaowei
AU - Pang, Minglun
AU - Zhang, Zhengbiao
AU - Zhu, Xiulin
AU - Zhu, Jian
AU - Du Prez, Filip E.
AU - Pan, Xiangqiang
N1 - Funding Information:
This work was supported by the National Natural Science Foundation of China (No. 21774080, 21302132, 21474068), the Natural Science Foundation of Jiangsu Province (BK20130296), the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions, the Joint research project of Jiangsu Province (BY2016051-01), the Educational Commission of Jiangsu Province of China (17KJA150008) and the Suzhou Key Lab of Macromolecular Design and Precision Synthesis.
Publisher Copyright:
© 2018 The Royal Society of Chemistry.
PY - 2018/8/7
Y1 - 2018/8/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85050723282&partnerID=8YFLogxK
U2 - 10.1039/c8py00736e
DO - 10.1039/c8py00736e
M3 - Article
AN - SCOPUS:85050723282
SN - 1759-9954
VL - 9
SP - 4044
EP - 4051
JO - Polymer Chemistry
JF - Polymer Chemistry
IS - 29
ER -