Sequential Triple 鈥淐lick鈥?Approach toward Polyhedral Oligomeric Silsesquioxane-Based Multiheaded and Multitailed Giant Surfactants

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• 作者：Hao Su ; Jukuan Zheng ; Zhao Wang ; Fei Lin ; Xueyan Feng ; Xue-Hui Dong ; Matthew L. Becker ; Stephen Z. D. Cheng ; Wen-Bin Zhang ; Yiwen Li
• 刊名：ACS Macro Letters
• 出版年：2013
• 出版时间：August 20, 2013
• 年：2013
• 卷：2
• 期：8
• 页码：645-650
• 全文大小：390K
• 年卷期：v.2,no.8(August 20, 2013)
• ISSN：2161-1653

文摘

This letter reports a sequential triple 鈥渃lick鈥?chemistry method for the precise synthesis of functional polyhedral oligomeric silsesquioxane (POSS)-based multiheaded and multitailed giant surfactants. A vinyl POSS-based heterobifunctional building block possessing two alkyne groups of distinct reactivity was used as a robust and powerful 鈥渃lickable鈥?precursor for ready access to a variety of POSS-based shape amphiphiles with complex architectures. The synthetic approach involves sequentially performed strain-promoted azide鈥揳lkyne cycloaddition (SPAAC), copper-catalyzed azide鈥揳lkyne cycloaddition (CuAAC), and thiol鈥揺ne 鈥渃lick鈥?coupling (TECC). Specifically, the first SPAAC reaction was found to be highly selective with no complications from the vinyl groups and terminal alkynes in the precursor. The method expands the toolbox of sequential 鈥渃lick鈥?approaches and broadens the scope of synthetically available giant surfactants for further study on structure鈥損roperty relationships.