Zwitterionic Ammonium Sulfonate Polymers: Synthesis and Properties in Fluids

Abstract

This article is dedicated to Rudolf Zentel in honor of his significant contributions to the fields of polymer chemistry, nanoscience, and polymeric biomaterials, as well as his promotion of international scientific collaboration and student exchange.Polymer zwitterions continue to emerge as useful materials for numerous applications, ranging from hydrophilic and antifouling coatings to electronic materials interfaces. While several polymer zwitterion compositions are now well established, interest in this field of soft materials science has grown rapidly in recent years due to the introduction of new structures that diversify their chemistry and architecture. Nonetheless, at present, the variation of the chemical composition of the anionic and cationic components of zwitterionic structures remains relatively limited to a few primary examples. In this article, the versatility of 4-vinylbenzyl sultone as a precursor to ammonium sulfonate zwitterionic monomers, which are then used in controlled free radical polymerization chemistry to afford "inverted sulfobetaine" polymer zwitterions, is highlighted. An evaluation of the solubility, interfacial activity, and solution configuration of the resultant polymers reveals the dependence of properties on the selection of tertiary amines used for nucleophilic ring-opening of the sultone precursor, as well as useful properties comparisons across different zwitterionic compositions.

Cell-membrane-inspired polymers for constructing biointerfaces with efficient molecular recognition

“…In terms of polymerization, high-molecular-weight polymers have been obtained by general radical polymerization and living polymerization, and have been copolymerized with various monomers. [136][137][138][139] Research on biointerfaces based on these polymers is progressing; the results have shown promise in terms of expressing new functions.…”

2-hydroxy-3-(1-(4-vinylbenzyl)imidazol-3-ium-3-yl)propane-1-sulfonate and 3-(4-vinylbenzyl)dimethylammonio)-2-hydroxypropane-1-sulfonate as New Zwitterionic Monomers

“…To prepare antifouling surfaces, methacrylate and acrylamide are the most common polymerizable groups used for zwitterionic monomers [2,3]. However, some studies reported the use of a styrenic polymerizable group [6,7]. Very recently, T. Emrick et al…”

“…described the preparation of new zwitterionic monomers using 4-vinylbenzyl sultone as precursor to ammonium sulfonate monomers [6].…”

2-Hydroxy-3-(1-(4-vinylbenzyl)imidazol-3-ium-3-yl)propane-1-sulfonate and 3-(4-Vinylbenzyl)dimethylammonio)-2-hydroxypropane-1-sulfonate as New Zwitterionic Monomers

“…However, some studies reported the Molbank 2022, 2022, M1414. https://doi.org/10.3390/M1414 https://www.mdpi.com/journal/molbank use of a styrenic polymerizable group [6,7]. Very recently, T. Emrick et al, described the preparation of new zwitterionic monomers using 4-vinylbenzyl sultone as a precursor to incorporating ammonium sulfonate units [6].…”

“…https://doi.org/10.3390/M1414 https://www.mdpi.com/journal/molbank use of a styrenic polymerizable group [6,7]. Very recently, T. Emrick et al, described the preparation of new zwitterionic monomers using 4-vinylbenzyl sultone as a precursor to incorporating ammonium sulfonate units [6]. Indeed, numerous studies reported in the literature have shown that excellent antibacterial and anti-fouling properties were achieved by combination of ammonium cationic parts with sulfonate anionic moiety [8,9].…”