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Exploring strain-promoted 1,3-dipolar cycloadditions of end functionalized polymers.

ABSTRACT: Strain-promoted 1,3-dipolar cycloaddition of cyclooctynes with 1,3-dipoles such as azides, nitrones, and nitrile oxides, are of interest for the functionalization of polymers. In this study, we have explored the use of a 4-dibenzocyclooctynol (DIBO)-containing chain transfer agent in reversible addition-fragmentation chain transfer polymerizations. The controlled radical polymerization resulted in well-defined DIBO-terminating polymers that could be modified by 1,3-dipolar cycloadditions using nitrones, nitrile oxides, and azides having a hydrophilic moiety. The self-assembly properties of the resulting block copolymers have been examined. The versatility of the methodology was further demonstrated by the controlled preparation of gold nanoparticles coated with the DIBO-containing polymers to produce materials that can be further modified by strain-promoted cycloadditions.

SUBMITTER: Ledin PA

PROVIDER: S-EPMC4113408 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Exploring strain-promoted 1,3-dipolar cycloadditions of end functionalized polymers.

Ledin Petr A PA Kolishetti Nagesh N Hudlikar Manish S MS Boons Geert-Jan GJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20140606 28

Strain-promoted 1,3-dipolar cycloaddition of cyclooctynes with 1,3-dipoles such as azides, nitrones, and nitrile oxides, are of interest for the functionalization of polymers. In this study, we have explored the use of a 4-dibenzocyclooctynol (DIBO)-containing chain transfer agent in reversible addition-fragmentation chain transfer polymerizations. The controlled radical polymerization resulted in well-defined DIBO-terminating polymers that could be modified by 1,3-dipolar cycloadditions using n ...[more]

PMID: 24906200

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