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Citation:
Kan Yue, Jinlin He, Chang Liu, Mingjun Huang, Xue-Hui Dong, Kai Guo, Peihong Ni, Chrys Wesdemiotis, Roderic P. Quirk, Stephen Z. D. Cheng, Wen-Bin Zhang. ANIONIC SYNTHESIS OF A “CLICKABLE” MIDDLE-CHAIN AZIDE-FUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES[J]. Chinese Journal of Polymer Science,
;2013, 31(1): 71-82.
doi:
10.1007/s10118-013-1215-x
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“Click chemistry” is, by definition, a general functionalization methodology (GFM) and its marriage with living anionic polymerization is particularly powerful in precise macromolecular synthesis. This paper reports the synthesis of a “clickable” middle-chain azide-functionalized polystyrene (mPS-N3) by anionic polymerization and its application in the preparation of novel shape amphiphiles based on polyhedral oligomeric silsesquioxane (POSS). The mPS-N3 was synthesized by coupling living poly(styryl)lithium chains (PSLi) with 3-chloropropylmethyldichlorosilane and subsequent nucleophilic substitution of the chloro group in the presence of sodium azide. Excess PSLi was end-capped with ethylene oxide to facilitate its removal by flash chromatography. The mPS-N3 was then derived into a giant lipid-like shape amphiphile in two steps following a sequential “click” strategy. The copper(I)-catalyzed azide-alkyne cycloaddition between mPS-N3 and alkyne-functionalized vinyl-substituted POSS derivative (VPOSS-alkyne) ensured quantitative ligation to give polystyrene with VPOSS tethered at the middle of the chain (mPS-VPOSS). The thiol-ene reaction with 1-thioglycerol transforms the vinyl groups on the POSS periphery to hydroxyls, resulting in an amphiphilic shape amphiphile, mPS-DPOSS. This synthetic approach is highly efficient and modular. It demonstrates the “click” philosophy of facile complex molecule construction from a library of simple building blocks and also suggests that mPS-N3 can be used as a versatile “clickable” motif in polymer science for the precise synthesis of complex macromolecules.
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Keywords:
- Living anionic polymerization
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