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 journalArticle

70 Citations (Scopus)

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

Fingerprint

Dendrimers
Anhydrides
Esterification
Alkenes
Sulfhydryl Compounds
Hydroxyl Radical
Olefins
Hydrogels
Interchanges
Macromolecules
Chemical properties
Polyethylene glycols
Physical properties
Monomers
Fabrication

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

Accelerated growth of dendrimers via thiol-ene and esterification reactions. / Montañez, Maria I.; Campos, Luis M.; Antoni, Per; Hed, Yvonne; Walter, Marie V.; Krull, Brandon T.; Khan, Anzar; Hult, Anders; Hawker, Craig J.; Malkoch, Michael.

In: Macromolecules, Vol. 43, No. 14, 27.07.2010, p. 6004-6013.

Research output: Contribution to journalArticle

Montañez, MI, Campos, LM, Antoni, P, Hed, Y, Walter, MV, Krull, BT, Khan, A, Hult, A, Hawker, CJ & Malkoch, M 2010, 'Accelerated growth of dendrimers via thiol-ene and esterification reactions', Macromolecules, vol. 43, no. 14, pp. 6004-6013. https://doi.org/10.1021/ma1009935
Montañez MI, Campos LM, Antoni P, Hed Y, Walter MV, Krull BT et al. Accelerated growth of dendrimers via thiol-ene and esterification reactions. Macromolecules. 2010 Jul 27;43(14):6004-6013. https://doi.org/10.1021/ma1009935
Montañez, Maria I. ; Campos, Luis M. ; Antoni, Per ; Hed, Yvonne ; Walter, Marie V. ; Krull, Brandon T. ; Khan, Anzar ; Hult, Anders ; Hawker, Craig J. ; Malkoch, Michael. / Accelerated growth of dendrimers via thiol-ene and esterification reactions. In: Macromolecules. 2010 ; Vol. 43, No. 14. pp. 6004-6013.
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