Premium
A Synthetic Route to Sulfobetaine Methacrylates with Varying Charge Distance
Author(s) -
Kratzer Domenic,
Barner Leonie,
Friedmann Christian,
Bräse Stefan,
Lahann Joerg
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402734
Subject(s) - chemistry , methacrylate , monomer , reagent , methacrylic acid , sulfonate , amine gas treating , polymerization , polymer chemistry , solvent , methylene , combinatorial chemistry , organic chemistry , polymer , sodium
A general synthetic strategy is described that enables access to a library of new sulfobetaine methacrylates starting from commercially available precursors. The three‐step procedure allows the distance between the quaternary amine and the sulfonate group (inner charge distance) to be varied by selecting the corresponding dibromoalkane in the first step. A key step is the final esterification, in which methacrylic acid acts as solvent as well as reagent for the zwitterionic hydroxy intermediates. Thus, it is possible to synthesize monomeric precursors with up to twelve methylene groups between the positive and the negative charge. A selection of these monomers has been successfully tested for their ability to polymerize using free‐radical polymerization.