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Versatile omega-End Group Functionalization of RAFT Polymers Using Functional Methane Thiosulfonates

Roth, PJ, Kessler, D, Zentel, R and Theato, P (2009) Versatile omega-End Group Functionalization of RAFT Polymers Using Functional Methane Thiosulfonates JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 47 (12). pp. 3118-3130.

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Abstract

Five different polymers, poly[methyl methacrylate] (PMMA), poly[lauryl methacrylate] (PLMA), poly[diethylene glycol methacrylate] (PDEGMA), poly[N-iso-propylacrylamide] (PNIPA), and poly[styrene] (PS) prepared by the RAFT process and thus terminated with dithioesters were aminolyzed in the presence of S-3-butynyl methane thiosulfonate (MTS), which was synthesized in two steps. Analysis of the polymers by 2D NMR, UV–vis absorbance, and gel permeation chromatogra-phy revealed them to quantitatively carry acetylene end groups connected with disul-fide bridges, indicating that functional MTS reagents can be employed for end group functionalization of RAFT polymers. This versatile method is of advantage compared with conjugations with functional maleimides, where isolation of terminal thiols is of-ten required but inexpedient for poly[(meth)acrylates] because their terminal thiols may undergo backbiting and thus avoid conjugation. The acetylene-terminated poly-mers were bound to an azide functionalized glass surface in a Cu(I) catalyzed cyclo-addition. The modified surfaces exhibited water contact angles corresponding to the polarity of the attached polymers. In the case of the stimulus responsive polymers PNIPA and PDEGMA, the surfaces showed temperature-dependent contact angles. The disulfide bond connecting the polymers to the surface could be selectively cleaved and resulted in all surfaces having the same contact angle, independent of the nature of the polymer prior attached to the surface.

Item Type: Article
Subjects : Chemistry
Authors :
AuthorsEmailORCID
Roth, PJUNSPECIFIEDUNSPECIFIED
Kessler, DUNSPECIFIEDUNSPECIFIED
Zentel, RUNSPECIFIEDUNSPECIFIED
Theato, PUNSPECIFIEDUNSPECIFIED
Date : 15 June 2009
Identification Number : 10.1002/pola.23392
Copyright Disclaimer : Copyright 2009 Wiley Periodicals Inc
Uncontrolled Keywords : Science & Technology, Physical Sciences, Polymer Science, POLYMER SCIENCE, click chemistry, end group functionalization, functionalization of polymers, reversible addition fragmentation chain transfer (RAFT), surfaces, FRAGMENTATION CHAIN TRANSFER, LIVING RADICAL POLYMERIZATION, CLICK CHEMISTRY, BLOCK-COPOLYMERS, INTRACELLULAR DELIVERY, SURFACE MODIFICATION, BIOMOLECULAR DRUGS, RESPONSIVE POLYMER, MODULAR SYNTHESIS, WATER
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 25 May 2016 13:11
Last Modified : 25 May 2016 13:11
URI: http://epubs.surrey.ac.uk/id/eprint/810821

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