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Hydrophobically Modified Sulfobetaine Copolymers with Tunable Aqueous UCST through Postpolymerization Modification of Poly(pentafluorophenyl acrylate)

Woodfield, PA, Zhu, Y, Pei, Y and Roth, PJ (2014) Hydrophobically Modified Sulfobetaine Copolymers with Tunable Aqueous UCST through Postpolymerization Modification of Poly(pentafluorophenyl acrylate) MACROMOLECULES, 47 (2). pp. 750-762.

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Abstract

Polysulfobetaines, polymers carrying highly polar zwitterionic side chains, present a promising research field by virtue of their antifouling properties, hemocompatibility, and stimulus-responsive behavior. However, limited synthetic approaches exist to produce sulfobetaine copolymers comprising hydrophobic components. Postpolymerization modification of an activated ester precursor, poly- (pentafluorophenyl acrylate), employing a zwitterionic amine, 3-((3-aminopropyl)dimethylammonio)propane-1-sulfonate, ADPS, is presented as a novel, one-step synthetic concept toward sulfobetaine (co)polymers. Modifications were performed in homogeneous solution using propylene carbonate as solvent with mixtures of ADPS and pentylamine, benzylamine, and dodecylamine producing a series of well-defined statistical acrylamido sulfobetaine copolymers containing hydrophobic pentyl, benzyl, or dodecylacrylamide comonomers with well-controllable molar composition as evidenced by NMR and FT-IR spectroscopy and size exclusion chromatography. This synthetic strategy was exploited to investigate, for the first time, the influence of hydrophobic modification on the upper critical solution temperature (UCST) of sulfobetaine copolymers in aqueous solution. Surprisingly, incorporation of pentyl groups was found to increase solubility over a wide composition range, whereas benzyl groups decreased solubilityan effect attributed to different entropic and enthalpic contributions of both functional groups. While UCST transitions of polysulfobetaines are typically limited to higher molar mass samples, incorporation of 0−65 mol % of benzyl groups into copolymers with molar masses of 25.5−34.5 kg/mol enabled sharp, reversible transitions from 6 to 82 °C in solutions containing up to 76 mM NaCl, as observed by optical transmittance and dynamic light scattering. Both synthesis and systematic UCST increase of sulfobetaine copolymers presented here are expected to expand the scope and applicability of these smart materials

Item Type: Article
Subjects : Chemistry
Authors :
AuthorsEmailORCID
Woodfield, PAUNSPECIFIEDUNSPECIFIED
Zhu, YUNSPECIFIEDUNSPECIFIED
Pei, YUNSPECIFIEDUNSPECIFIED
Roth, PJUNSPECIFIEDUNSPECIFIED
Date : 28 January 2014
Identification Number : 10.1021/ma402391a
Uncontrolled Keywords : Science & Technology, Physical Sciences, Polymer Science, CRITICAL SOLUTION TEMPERATURE, RAFT POLYMERIZATION, SOLUTION BEHAVIOR, SULFONATOPROPYLBETAINE COPOLYMERS, POLY(SULFOBETAINE METHACRYLATE), THERMORESPONSIVE PROPERTIES, ZWITTERIONIC COPOLYMERS, 2-METHOXYETHYL ACRYLATE, 2-HYDROXYETHYL ACRYLATE, RADICAL POLYMERIZATION
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 11 May 2016 11:46
Last Modified : 11 May 2016 11:46
URI: http://epubs.surrey.ac.uk/id/eprint/810670

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