Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets

doi:10.1002/app.44410

CORC > 重庆绿色智能技术研究院 > 中国科学院重庆绿色智能技术研究院 > 机器人与3D打印技术创新中心

	Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets
	Cao, Liangcheng1 ; Wang, Yuechuan 2
刊名	JOURNAL OF APPLIED POLYMER SCIENCE
	2017-01-20
卷号	134 期号:4 页码:8
关键词	biopolymers and renewable polymers cellulose and other wood products grafting synthesis and processing
ISSN号	0021-8995
DOI	10.1002/app.44410
通讯作者	Cao, LC (reprint author), Chinese Acad Sci, Chongqing Inst Green & Intelligent Technol, Fangzheng Ave 266, Chongqing 400714, Peoples R China.
英文摘要	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.
资助项目	Natural Science Foundation of China[61505208]
WOS研究方向	Polymer Science
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000386939600024
内容类型	期刊论文
源URL	[http://172.16.51.4:88/handle/2HOD01W0/272]
专题	机器人与3D打印技术创新中心
通讯作者	Cao, Liangcheng
作者单位	1.Chinese Acad Sci, Chongqing Inst Green & Intelligent Technol, Fangzheng Ave 266, Chongqing 400714, Peoples R China 2.Sichuan Univ, Coll Polymer Sci & Engn, State Key Lab Polymer Mat, Chengdu 610065, Peoples R China
推荐引用方式 GB/T 7714	Cao, Liangcheng,Wang, Yuechuan. Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets[J]. JOURNAL OF APPLIED POLYMER SCIENCE,2017,134(4):8.
APA	Cao, Liangcheng,&Wang, Yuechuan.(2017).Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets.JOURNAL OF APPLIED POLYMER SCIENCE,134(4),8.
MLA	Cao, Liangcheng,et al."Alkyne cellulose for Huisgen [3+2] cycloaddition with azido-terminated targets".JOURNAL OF APPLIED POLYMER SCIENCE 134.4(2017):8.