Discrete and Stereospecific Oligomers Prepared by Sequential and Alternating Single Unit Monomer Insertion

Journal of the American Chemical Society
Zixuan HuangJiangtao Xu

Abstract

Natural biopolymers, such as DNA and proteins, have uniform microstructures with defined molecular weight, precise monomer sequence, and stereoregularity along the polymer main chain that affords them unique biological functions. To reproduce such structurally perfect polymers and understand the mechanism of specific functions through chemical approaches, researchers have proposed using synthetic polymers as an alternative due to their broad chemical diversity and relatively simple manipulation. Herein, we report a new methodology to prepare sequence-controlled and stereospecific oligomers using alternating radical chain growth and sequential photoinduced RAFT single unit monomer insertion (photo-RAFT SUMI). Two families of cyclic monomers, the indenes and the N-substituted maleimides, can be alternatively inserted into RAFT agents, one unit at a time, allowing the monomer sequence to be controlled through sequential and alternating monomer addition. Importantly, the stereochemistry of cyclic monomer insertion into the RAFT agents is found to be trans-selective along the main chains due to steric hindrance from the repeating monomer units. All investigated cyclic monomers provide such trans-selectivity, but analogous acyclic mo...Continue Reading

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Citations

Nov 12, 2019·Macromolecular Rapid Communications·Yanyan ZhouGraeme Moad
Dec 29, 2018·Beilstein Journal of Organic Chemistry·Atsushi KagaShunsuke Chiba
Jul 23, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Kevin KafutaManuel Alcarazo
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Jun 10, 2021·Nature Chemistry·Subhajit PalAndreas F M Kilbinger
Mar 14, 2020·Journal of the American Chemical Society·Michael L McGrawEugene Y-X Chen
Mar 6, 2019·Journal of the American Chemical Society·Bo ZhaoChao Gao
Sep 29, 2021·Journal of the American Chemical Society·Joji TanakaWei You
Oct 7, 2021·Advanced Materials·Kenward JungCyrille Boyer
Dec 2, 2021·Macromolecular Rapid Communications·Ruizhe LiuJiangtao Xu

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