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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Copolymers
Azides
Ketones
Aldehydes
Hydrazones
Cycloaddition
Ring opening polymerization
Gel permeation chromatography
Macromolecules
Drug delivery
Organic solvents
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Polymers
Molecules

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Modular covalent multifunctionalization of copolymers. / Yang, Si Kyung; Weck, Marcus.

In: Macromolecules, Vol. 41, No. 2, 22.01.2008, p. 346-351.

Research output: Contribution to journalArticle

Yang, Si Kyung ; Weck, Marcus. / Modular covalent multifunctionalization of copolymers. In: Macromolecules. 2008 ; Vol. 41, No. 2. pp. 346-351.
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