Thiol-Michael &quot;click&quot; chemistry: another efficient tool for head   functionalization of giant surfactants

doi:10.1039/c4py01103a

CORC > 北京大学 > 化学与分子工程学院

	Thiol-Michael "click" chemistry: another efficient tool for head functionalization of giant surfactants
	Li, Yiwen ; Su, Hao ; Feng, Xueyan ; Wang, Zhao ; Guo, Kai ; Wesdemiotis, Chrys ; Fu, Qiang ; Cheng, Stephen Z. D. ; Zhang, Wen-Bin
刊名	polymer chemistry
	2014
关键词	POLYHEDRAL OLIGOMERIC SILSESQUIOXANE SHAPE AMPHIPHILES ENE CLICK GEMINI SURFACTANTS ADDITION-REACTIONS BUILDING-BLOCKS POLYMER FACILE POSS BIOCONJUGATION
DOI	10.1039/c4py01103a
英文摘要	One of the challenges in the precise synthesis of giant surfactants lies in the homogenous functionalization of a head with bulky ligands. In this article, we report the use of thiol-Michael "click" chemistry as a facile, modular and robust approach to address this issue. A giant surfactant with acryloxyl-functionalized POSS (ACPOSS) head was conveniently constructed from commercially available acrylo POSS and polystyrene (PS). Functional thiols with different sizes, such as 2-mercaptoethanol, 1H, 1H, 2H, 2H-perfluoro-1-decanethiol, 1-thio-beta-D-glucose tetraacetate (sugar-SH), and 2-naphthalenethiol, were attached onto the head of the ACPOSS-PS conjugate by thiol-Michael and thiol-ene reactions. It was found that while both the methods offer a straightforward and highly efficient approach to prepare uniform and precise giant surfactants with small thiol ligands, only the former proceeds without apparent side reactions when large and bulky thiols, such as sugar-SH and 2-naphthalenethiol, are used. The former method also eliminates the need for UV irradiation or heat initiation. Therefore, the mild condition, high efficiency, and broad functional group tolerance of thiol-Michael chemistry should further expand the scope of POSS-based giant surfactants with unparalleled possibilities for head surface chemistry manipulation, which provides numerous opportunities for nanofabrication by the direct self-assembly of giant surfactants.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000342761200004&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Polymer Science; SCI(E); EI; 10; ARTICLE; scheng@uakron.edu; wenbin@pku.edu.cn; 21; 6151-6162; 5
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/217306]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Li, Yiwen,Su, Hao,Feng, Xueyan,et al. Thiol-Michael "click" chemistry: another efficient tool for head functionalization of giant surfactants[J]. polymer chemistry,2014.
APA	Li, Yiwen.,Su, Hao.,Feng, Xueyan.,Wang, Zhao.,Guo, Kai.,...&Zhang, Wen-Bin.(2014).Thiol-Michael "click" chemistry: another efficient tool for head functionalization of giant surfactants.polymer chemistry.
MLA	Li, Yiwen,et al."Thiol-Michael "click" chemistry: another efficient tool for head functionalization of giant surfactants".polymer chemistry (2014).