Title

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

Publication Date

2019

Comments

full-text forthcoming

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.

Journal or Book Title

Journal of the American Chemical Society

Pages

13619-13624

DOI

https://doi.org/10.1021/jacs.9b06328

Volume

141

Issue

34

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