ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES

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

doi:10.1007/s10118-013-1215-x

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ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES

Special Issue: The 10th International Symposium on Polymer Physics (2012) | Updated：2023-01-03

- ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES
- ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES
- Chinese Journal of Polymer Science 2013年31卷第1期页码：71-82
- Affiliations：
  
  a.Department of Polymer Science, College of Polymer Science and Polymer Engineering, The University of Akron, Akron, Ohio 44325-3909, USA
  b.College of Chemistry, Chemical Engineering, and Materials Science, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Soochow University, Suzhou 215123, China
  c.Department of Chemistry, The University of Akron, Akron, Ohio 44325-3601, USA
- Author bio：
  
  *Stephen Z. D. Cheng, E-mail: scheng@uakron.edu
  Wen-Bin Zhang, E-mail: wz8@uakron.edu
- Funds：
- DOI：10.1007/s10118-013-1215-x
  中图分类号：
- 收稿：2012-09-25，
  
  修回：2012-10-08，
  
  录用：2012-10-10，
  
  纸质出版：2013-01
- Accepted：
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Kan Yue, Jinlin He, Chang Liu, 等. ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES[J]. Chinese Journal of Polymer Science, 2013,31(1):71-82.

Kan Yue, Jinlin He, Chang Liu, et al. ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED POLYSTYRENE AND ITS APPLICATION IN SHAPE AMPHIPHILES[J]. Chinese Journal of Polymer Science, 2013, 31(1): 71-82.
Kan Yue, Jinlin He, Chang Liu, 等. ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED 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.

Kan Yue, Jinlin He, Chang Liu, et al. ANIONIC SYNTHESIS OF A "CLICKABLE" MIDDLE-CHAIN AZIDEFUNCTIONALIZED 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.

摘要

Abstract

"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-N

) by anionic polymerization and its application in the preparation of novel shape amphiphiles based on polyhedral oligomeric silsesquioxane (POSS). The mPS-N

was synthesized by coupling living poly(styryl)lithium chains (PSLi) with 3-chloropropylmethyldichlorosilane and subsequent nucleophilic substitution of the chloro group in the pres

ence of sodium azide. Excess PSLi was end-capped with ethylene oxide to facilitate its removal by flash chromatography. The mPS-N

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-N

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-N

can be used as a versatile "clickable" motif in polymer science for the precise synthesis of complex macromolecules.

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