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Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets
Cao, Liangcheng1; Wang, Yuechuan2
2017-01-20
摘要Azido-grafted cellulose has been reported widely applied for further functionalization by click chemistry. As an alternative method, we proposed alkyne-grafted cellulose as a prototype molecule for Huisgen [3+2] cycloaddition with azido-terminated target compounds. Alkyne cellulose was synthesized by acylation with prop-2-ynyl 5-chloro-5-oxopentanoate and, subsequently cycloaddition with 4-aminophenylazide, ethyl 2-azidoacetate, and (S)-2-(Azidomethyl)-1-(tert-butoxycarbonyl)pyrrolidine (Boc-pyrrolidine azide) to form triazole cellulose in a click manner. The reactions were confirmed qualitatively by Fourier transform infrared and NMR spectroscopy and analyzed quantitatively with elemental analysis data. The results show that a degree of substitution of up to 1.91 was obtained for esterification and, in most cases, was preferred completely in a selective way for the primary hydroxyl groups at the O-6 position and partially at the O-2 and O-3 positions. Cycloaddition conversions were found as high as 0.95, 0.99, and 0.99 for aniline-triazole cellulose, acetate-triazole cellulose, and Boc-pyrrolidine-triazole cellulose, respectively. Both esterification and cycloaddition were undertaken under mild conditions without additional heating. (c) 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44410.
关键词biopolymers and renewable polymers cellulose and other wood products grafting synthesis and processing
DOI10.1002/app.44410
发表期刊JOURNAL OF APPLIED POLYMER SCIENCE
ISSN0021-8995
卷号134期号:4页码:8
通讯作者Cao, LC (reprint author), Chinese Acad Sci, Chongqing Inst Green & Intelligent Technol, Fangzheng Ave 266, Chongqing 400714, Peoples R China.
收录类别SCI
WOS记录号WOS:000386939600024
语种英语