Modular covalent multifunctionalization of copolymers

Si Kyung Yang, Marcus Weck

Research output: Contribution to journalArticle

Abstract

Poly(norbornene)-based random copolymers possessing either azide, aldehyde, or ketone functionalities on each repeating unit were synthesized using ring-opening metathesis polymerization. The orthogonal functionalization of the resulting copolymers using 1,3-dipolar cycloadditions and hydrazone formations was investigated. While the azide- and aldehyde-containing copolymers were insoluble in organic solvents, the azideand ketone-functionalized copolymers were fully soluble in common solvents such as CH2Cl2, THF, and DMF and can be quantitatively functionalized with a library of small organic and biological molecules in a stepwise fashion. The orthogonal functionalization of the ketone/azide copolymers was characterized by NMR and IR spectroscopies and gel-permeation chromatography. A one-pot dual functionalization strategy is also presented that allows for the quantitative dual functionalization of copolymers. This one-pot strategy introduced herein for the preparation of multifunctional macromolecules provides a modular platform for potential applications ranging from electronic materials to polymer-mediated drug delivery.

Original languageEnglish (US)
Pages (from-to)346-351
Number of pages6
JournalMacromolecules
Volume41
Issue number2
DOIs
StatePublished - Jan 22 2008

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ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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