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

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          Abstract

          A chemoselective thiol-Michael addition reaction allows access to oxamide-containing segmented copolymers using a one-pot, one-step procedure.

          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.

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          Most cited references56

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          Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis.

          The merits of thiol-click chemistry and its potential for making new forays into chemical synthesis and materials applications are described. Since thiols react to high yields under benign conditions with a vast range of chemical species, their utility extends to a large number of applications in the chemical, biological, physical, materials and engineering fields. This critical review provides insight into emerging venues for application as well as new mechanistic understanding of this exceptional chemistry in its many forms (81 references).
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            Michael addition reactions in macromolecular design for emerging technologies

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              Nucleophile-Initiated Thiol-Michael Reactions: Effect of Organocatalyst, Thiol, and Ene

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                Author and article information

                Journal
                PCOHC2
                Polymer Chemistry
                Polym. Chem.
                Royal Society of Chemistry (RSC)
                1759-9954
                1759-9962
                2017
                2017
                : 8
                : 17
                : 2598-2608
                Affiliations
                [1 ]Department of Chemistry
                [2 ]Macromolecules Innovation Institute
                [3 ]Virginia Tech
                [4 ]Blacksburg
                [5 ]USA
                Article
                10.1039/C7PY00021A
                3f07543e-a77d-444f-ba85-1d2517272ad3
                © 2017
                History

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