Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties

doi:10.1021/ma800976e

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	Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties
	Cheuk, Kevin K. L.1; Li, Bing Shi 1,2; Lam, Jacky W. Y.1; Xie, Yong 4; Tang, Ben Zhong 1,3
刊名	MACROMOLECULES
	2008-08-26
卷号	41 期号:16 页码:5997-6005
ISSN号	0024-9297
DOI	10.1021/ma800976e
英文摘要	A functional phenylacetylene monomer containing a naturally occurring building block Of L-alanine, namely 4-ethynylbenzoyl-L-alanine methyl ester (PA-Ae), was synthesized. The monomer was polymerized by organorhodium catalysts, giving the corresponding "polyester" (PPA-Ae) with high molecular weights (M-w up to 1.2 x 10(6)) and stereoregularities (Z content up to 97%) in high yields (up to similar to 91 %). The polyene backbone of PPA-Ae undergoes irreversible Z-to-E isomerization at similar to 180-250 degrees C. The ester groups in the pendants of the polymer are selectively deprotected by the base-catalyzed hydrolysis, producing a "polyacid" with "free" L-alanine pendants (PPA-A). While PA-Ae monomer is CD-inactive at wavelengths longer than 300 nm, both PPA-Ae and PPA-A polymers exhibit strong Cotton effects in the long wavelength region where their polyene backbones absorb, indicating that the chiral pendants have induced the polymer chain to take a helical conformation with an excess in one-handedness. Upon natural evaporation of its solutions, the amphiphilic chains of PPA-Ae self-associate in a cooperative fashion, furnishing a variety of organizational morphologies including twisting cables, spiral ribbons, spherical vesicles, and helical nanotubes. The polymers are biocompatible: the living cells are all survived after they have been subcultured in the presence of the polymers.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000258580700012
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64535]
专题	中国科学院化学研究所
通讯作者	Tang, Ben Zhong
作者单位	1.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China 2.Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China 3.Zhejiang Univ, Dept Polymer Sci & Engn, Hangzhou 310027, Zhejiang, Peoples R China 4.Hong Kong Univ Sci & Technol, Dept Biol, Kowloon, Hong Kong, Peoples R China
推荐引用方式 GB/T 7714	Cheuk, Kevin K. L.,Li, Bing Shi,Lam, Jacky W. Y.,et al. Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties[J]. MACROMOLECULES,2008,41(16):5997-6005.
APA	Cheuk, Kevin K. L.,Li, Bing Shi,Lam, Jacky W. Y.,Xie, Yong,&Tang, Ben Zhong.(2008).Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties.MACROMOLECULES,41(16),5997-6005.
MLA	Cheuk, Kevin K. L.,et al."Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties".MACROMOLECULES 41.16(2008):5997-6005.