Jump to main content
Jump to site search

Issue 7, 2012
Previous Article Next Article

A facile synthesis of clickable and acid-cleavable PEO for acid-degradable block copolymers

Author affiliations

Abstract

End-functionalized polyethylene oxides containing cleavable acetal and clickable azide terminal groups (PEO-acetal-N3 and N3-acetal-PEO-acetal-N3) were obtained by the reaction between commercially available PEOs and 2-chloroethyl vinyl ether using pyridinium p-toluenesulfonate. This results in acetal-linkages which can be further functionalized by nucleophilic displacement with sodium azide. Both reactions proceeded quantitatively to produce clickable and cleavable PEOs in good yields. The obtained PEOs were subsequently converted into macroinitiators for nitroxide-mediated polymerization (NMP) by “click” reaction with an alkyne functionalized alkoxyamine. Styrene polymerization from the macroinitiators proceeded successfully to give well-defined acid degradable block copolymers (PEO-acetal-PS and PS-acetal-PEO-acetal-PS), all of which were shown to have narrow molecular weight distributions (Mw/Mn ∼ 1.2). Significantly, highly ordered nanophase separated thin films of hexagonally-packed cylindrical PEO domains embedded in a PS matrix could be prepared from the PEO-acetal-PS diblock copolymers with removal of the PEO block by treatment with acid yielding nanoporous thin films with primary hydroxyl groups decorating the pores' interiors.

Graphical abstract: A facile synthesis of clickable and acid-cleavable PEO for acid-degradable block copolymers

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Oct 2011, accepted on 07 Nov 2011 and first published on 21 Nov 2011


Article type: Paper
DOI: 10.1039/C1PY00484K
Citation: Polym. Chem., 2012,3, 1890-1898
  •   Request permissions

    A facile synthesis of clickable and acid-cleavable PEO for acid-degradable block copolymers

    K. Satoh, J. E. Poelma, L. M. Campos, B. Stahl and C. J. Hawker, Polym. Chem., 2012, 3, 1890
    DOI: 10.1039/C1PY00484K

Search articles by author

Spotlight

Advertisements