Activated Polyacrylamides as Versatile Substrates for Postpolymerization Modification

Michael Larsen, Shannon Herzog, Helena Quilter, Marc Hillmyer

Research output: Contribution to journalArticle

Abstract

The displacement of an activated leaving group in polymeric repeat units is a powerful method of postpolymerization modification. This strategy enables the synthesis of polymers otherwise unobtainable by direct polymerization as well as the preparation of a diverse array of macromolecular structures. We demonstrate that the activation of acrylamide through the introduction of two tert-butyloxycarbamate (Boc) groups followed by radical polymerization leads to a new class of activated polyacrylamides analogous to well-known activated polyacrylates. Transamidation of poly(di(Boc)-acrylamide) utilizing primary amines proceeds to high conversion under mild conditions, and the products can be readily purified. Less nucleophilic secondary amines and alcohols require more forcing conditions. We demonstrate the utility of this approach by preparing copolymers capable of on-demand gel formation and the synthesis of block polymers using controlled radical polymerization.
LanguageEnglish
Pages122-126
JournalACS Macro Letters
Volume7
Early online date4 Jan 2018
DOIs
StatusPublished - 2018

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Acrylamide
Free radical polymerization
Polyacrylates
Amines
Substrates
Block copolymers
Polymers
Alcohols
Gels
Copolymers
Chemical activation
Polymerization
polyacrylamide

Cite this

Activated Polyacrylamides as Versatile Substrates for Postpolymerization Modification. / Larsen, Michael ; Herzog, Shannon ; Quilter, Helena; Hillmyer, Marc.

In: ACS Macro Letters, Vol. 7, 2018, p. 122-126.

Research output: Contribution to journalArticle

Larsen, Michael ; Herzog, Shannon ; Quilter, Helena ; Hillmyer, Marc. / Activated Polyacrylamides as Versatile Substrates for Postpolymerization Modification. In: ACS Macro Letters. 2018 ; Vol. 7. pp. 122-126
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