Accelerated growth of dendrimers via thiol-ene and esterification reactions

Maria I. Montañez, Luis M. Campos, Per Antoni, Yvonne Hed, Marie V. Walter, Brandon T. Krull, Anzar Khan, Anders Hult, Craig J. Hawker, Michael Malkoch

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Abstract

By taking advantage of the orthogonal nature of thiol-ene coupling and anhydride based esterification reactions, a facile and chemoselective strategy to dendritic macromolecules has been developed. The ability to interchange growth steps based on thiol-ene and anhydride chemistry allows the synthesis of fifth-generation dendrimers in only five steps and under benign reaction conditions. In addition, the presented coupling chemistries eliminate the traditional need for protection/deprotection steps and afford dendrimers in high yield and purity. The modularity of this strategy coupled with the latent reactivity of the alkene/hydroxyl chain ends was demonstrated by using different cores (alkene and hydroxyl functional), various AB2 and CD 2 monomers and a range of chain end groups. As a result, three dendritic libraries were prepared which exhibited tunability of both the chemical functionality and physical properties including the fabrication of PEG hydrogels.

Original languageEnglish
Pages (from-to)6004-6013
Number of pages10
JournalMacromolecules
Volume43
Issue number14
DOIs
Publication statusPublished - 2010 Jul 27
Externally publishedYes

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ASJC Scopus subject areas

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

Cite this

Montañez, M. I., Campos, L. M., Antoni, P., Hed, Y., Walter, M. V., Krull, B. T., ... Malkoch, M. (2010). Accelerated growth of dendrimers via thiol-ene and esterification reactions. Macromolecules, 43(14), 6004-6013. https://doi.org/10.1021/ma1009935