Orthogonal "relay" reactions for designing functionalized soft nanoparticles

Hamilton Kakwere, Sébastien Perrier

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68 Citations (Scopus)


The combination of reversible addition-fragmentation chain transfer (RAFT) chemistry followed by thiol-based "click" chemistry, known as an orthogonal "relay" reaction as one step complements the other, was used to produce surface-functionalized soft nanoparticles. Thiocarbonyl thio compounds were first used in the presence of vinyl monomers and a source of radicals to control the growth of the polymeric chains (via the RAFT process) and then reduced to thiols and utilized as a handle for functionalization of the resulting polymer chain ends (via a thiol-based click reaction). Both reactions occur under mild conditions and offer excellent control over the properties of the final product, and the thiol addition shows all the benefits of a click reaction, without requiring the use of a catalyst. This simple chemistry opens up the route to the production of a wide range of functional materials, and the concept is illustrated by the formation of nanoparticle-based gels, fluorescent-tagged particles, and protein-nanoparticle conjugates.

Original languageEnglish
Pages (from-to)1889-1895
Number of pages7
JournalJournal of the American Chemical Society
Issue number5
Publication statusPublished - 11 Feb 2009
Externally publishedYes

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