Jump to main content
Jump to site search

Issue 2, 2011
Previous Article Next Article

Polymerization of an activated ester monomer based on 4-vinylsulfonic acid and its polymer analogous reaction

Author affiliations

Abstract

Homopolymers containing sulfonic ester side groups were synthesized by reversible addition–fragmentation chain transfer (RAFT) polymerization utilizing benzyl dithiobenzoate, cumyl dithiobenzoate, and 4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic acid as chain transfer agents. Likewise diblock copolymers containing poly(styrene), poly(octylstyrene) and poly(pentafluorostyrene) as the second block were synthesized. Additionally, nitroxide mediated polymerization (NMP) was investigated for the synthesis of a homopolymer as well as for a diblock copolymer. Furthermore, the post-polymerization functionalization with various amines to yield the respective sulfonamides was conducted. The conversion was analyzed by 1H NMR spectroscopy, 19F NMR spectroscopy and FT-IR spectroscopy and in many cases a very high conversion (>96%) was observed. In addition the reaction kinetics of the post-polymerization functionalization of poly(pentafluorophenyl 4-vinylbenzene sulfonate) and the corresponding carboxyl ester poly(pentafluorophenyl 4-vinylbenzoate) were compared by analysis of the reactions by time-resolved 19F NMR spectroscopy. It was found that poly(pentafluorophenyl 4-vinylbenzoate) showed a higher stability towards hydrolysis and a significantly higher reactivity, resulting in complete conversions with different amines.

Graphical abstract: Polymerization of an activated ester monomer based on 4-vinylsulfonic acid and its polymer analogous reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 Aug 2010, accepted on 23 Sep 2010 and first published on 15 Oct 2010


Article type: Paper
DOI: 10.1039/C0PY00261E
Citation: Polym. Chem., 2011,2, 376-384
  •   Request permissions

    Polymerization of an activated ester monomer based on 4-vinylsulfonic acid and its polymer analogous reaction

    K. Nilles and P. Theato, Polym. Chem., 2011, 2, 376
    DOI: 10.1039/C0PY00261E

Search articles by author

Spotlight

Advertisements