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

Research output: Contribution to journalArticlepeer-review

85 Citations (Scopus)


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
Issue number14
Publication statusPublished - 2010 Jul 27
Externally publishedYes

ASJC Scopus subject areas

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


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