Polyelectrolytes with Tunable Charge Based on Polydehydroalanine: Synthesis and Solution Properties

Authors

  • Ulrike Günther,

    1. Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Jena, Germany
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  • Larisa V. Sigolaeva,

    1. Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russia
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  • Dmitry V. Pergushov,

    1. Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russia
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  • Felix H. Schacher

    Corresponding author
    1. Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Jena, Germany
    • Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Jena, Germany
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E-mail: felix.schacher@uni-jena.de

Abstract

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Poly(tert-butoxycarbonylaminomethylacrylate) (PtBAMA), a derivative of polydehydroalanine (PDha), is synthesized using free radical polymerization (FRP) and nitroxide mediated polymerization (NMP). Due to the presence of orthogonal protective groups, the resulting polymers can be selectively deprotected to yield either a polyanion (poly(tert-butoxycarbonylaminoacrylic acid), PtBAA) or a polycation (poly(aminomethylacrylate), PAMA). Deprotection of both the amino- and the carboxyl-functionality in a sequential manner leads to the potential polyzwitterion polydehydroalanine (PDha). The pH-dependent solution behavior of PtBAA, PAMA, and PDha are examined in aqueous solution by potentiometric and turbidimetric titrations as well as ζ-potential measurements.

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