Norbornadienes: Robust and Scalable Building Blocks for Cascade "Click" Coupling of High Molecular Weight Polymers.

ABSTRACT: Herein, we report the development of a scalable and synthetically robust building block based on norbornadiene (NBD) that can be broadly incorporated into a variety of macromolecular architectures using traditional living polymerization techniques. By taking advantage of a selective and rapid deprotection with tetrazine, highly reactive "masked" cyclopentadiene (Cp) functionalities can be introduced into synthetic polymers as chain-end groups in a quantitative and efficient manner. The orthogonality of this platform further enables a cascade "click" process where the "unmasked" Cp can rapidly react with dienophiles, such as maleimides, through a conventional Diels-Alder reaction. Coupling proceeds with quantitative conversions allowing high molecular weight star and dendritic block copolymers to be prepared in a single step under ambient conditions.

SUBMITTER: St Amant AH 

PROVIDER: S-EPMC7581381 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature