Issue 3, 2014

Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: mechanistic insight and application to organocatalysis

Abstract

A number of copolymers between styrene (St) or 4-azidomethylstyrene (N3St) and 2,3,4,5,6-pentafluorostyrene (FSt) have been prepared by atom-transfer radical polymerization (ATRP) and conventional free radical polymerization (FRP). The mode of monomer alternation in copolymers has been established unambiguously using heteronuclear multiple bond correlation (HMBC) NMR. The degree and nature of monomer alternation was found to be strongly dependent on both the solvent (or lack thereof) and the polymerization initiator. These results are in contrast to previously published studies, which rely primarily on classic analysis of monomer reactivity ratios. We proceeded to independently functionalize the N3St and FSt moieties using orthogonal “click” chemistries: copper-catalyzed azide–alkyne cycloaddition (CuAAC) and fluoroarene–thiol coupling (FTC). An alternating copolymer bearing –NH2 and –SO3 functional groups was found to be a competent organocatalyst for a Henry reaction between benzaldehyde and nitromethane.

Graphical abstract: Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: mechanistic insight and application to organocatalysis

Supplementary files

Article information

Article type
Communication
Submitted
30 Sep 2013
Accepted
25 Oct 2013
First published
29 Oct 2013

Polym. Chem., 2014,5, 698-701

Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: mechanistic insight and application to organocatalysis

J. O'Shea, V. Solovyeva, X. Guo, J. Zhao, N. Hadjichristidis and V. O. Rodionov, Polym. Chem., 2014, 5, 698 DOI: 10.1039/C3PY01368E

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