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

Authors
  • St. Amant, Andre H
  • Discekici, Emre H
  • Bailey, Sophia J
  • Zayas, Manuel S
  • Song, Jung-Ah
  • Shankel, Shelby L
  • Nguyen, Shay N
  • Bates, Morgan W
  • Anastasaki, Athina
  • Hawker, Craig J
  • de Alaniz, Javier Read
Publication Date
Aug 28, 2019
Source
eScholarship - University of California
Keywords
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Unknown
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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.

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