Poly(β-thioesters) containing monodisperse oxamide hard segments using a chemoselective thiol-Michael addition reaction

Nicholas G. Moon, Ryan J. Mondschein, Timothy Edward Long

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The inherent chemoselectivity of the thiol-Michael addition reaction enabled the synthesis of segmented copolymers using a one-pot, one-step procedure. The enhanced reactivity of a thiol towards an acrylate over a methacrylate generated thiol-terminated soft segment oligomers in the presence of bis-oxamide dimethacrylate hard segment monomers, furnishing segmented copolymers containing monodisperse hard segments after in situ chain extension. Thermomechanical characterization revealed extended plateau regions for all compositions with segmented and unsegmented copolymer analogs displaying similar plateau moduli, glass transition temperatures, and flow temperatures. Preliminary morphological analysis indicated a degree of undesired phase-mixing as a result of hydrogen-bond acceptors in the soft segment. The effectiveness of the bis-oxamide hydrogen-bonding motif allowed for sufficient phase separation to provide extended plateau regions for all samples as observed with dynamic mechanical analysis.

Original languageEnglish
Pages (from-to)2598-2608
Number of pages11
JournalPolymer Chemistry
Volume8
Issue number17
DOIs
Publication statusPublished - 2017 May 7
Externally publishedYes

Fingerprint

Addition reactions
Sulfhydryl Compounds
Copolymers
Hydrogen bonds
Transition flow
Methacrylates
Transition Temperature
Dynamic mechanical analysis
Hydrogen Bonding
Oligomers
Phase separation
Glass
Hydrogen
Monomers
Temperature
Chemical analysis
oxamide

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Biomedical Engineering
  • Polymers and Plastics
  • Organic Chemistry

Cite this

Poly(β-thioesters) containing monodisperse oxamide hard segments using a chemoselective thiol-Michael addition reaction. / Moon, Nicholas G.; Mondschein, Ryan J.; Long, Timothy Edward.

In: Polymer Chemistry, Vol. 8, No. 17, 07.05.2017, p. 2598-2608.

Research output: Contribution to journalArticle

Moon, Nicholas G. ; Mondschein, Ryan J. ; Long, Timothy Edward. / Poly(β-thioesters) containing monodisperse oxamide hard segments using a chemoselective thiol-Michael addition reaction. In: Polymer Chemistry. 2017 ; Vol. 8, No. 17. pp. 2598-2608.
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