Structurally diverse dendritic libraries

A highly efficient functionalization approach using click chemistry

Michael Malkoch, Kristin Schleicher, Eric Drockenmuller, Craig J. Hawker, Thomas P. Russell, Peng Wu, Valery V. Fokin

Research output: Contribution to journalArticle

350 Citations (Scopus)

Abstract

The high fidelity and efficiency of Click chemistry are exploited in the synthesis of a library of chain end functionalized dendritic macromolecules. In this example, the selectivity of the Cu-catalyzed [3 + 2π] cycloaddition reaction of azides with terminal acetylenes, coupled with mild reaction conditions, permits unprecedented functional group tolerance during the derivatization of dendrimeric and hyperbranched scaffolds. The resulting dendritic libraries are structurally diverse, encompassing a variety of backbones/surface functional groups, and are prepared in almost quantitative yields under very mild conditions. The robust and simple nature of this procedure, combined with its applicability to many aspects of polymer synthesis and materials chemistry, demonstrates an evolving synergy between advanced organic chemistry and functional materials.

Original languageEnglish (US)
Pages (from-to)3663-3678
Number of pages16
JournalMacromolecules
Volume38
Issue number9
DOIs
StatePublished - May 3 2005
Externally publishedYes

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Functional groups
Functional materials
Alkynes
Azides
Cycloaddition
Acetylene
Macromolecules
Scaffolds
Polymers
Organic Chemistry

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Malkoch, M., Schleicher, K., Drockenmuller, E., Hawker, C. J., Russell, T. P., Wu, P., & Fokin, V. V. (2005). Structurally diverse dendritic libraries: A highly efficient functionalization approach using click chemistry. Macromolecules, 38(9), 3663-3678. https://doi.org/10.1021/ma047657f

Structurally diverse dendritic libraries : A highly efficient functionalization approach using click chemistry. / Malkoch, Michael; Schleicher, Kristin; Drockenmuller, Eric; Hawker, Craig J.; Russell, Thomas P.; Wu, Peng; Fokin, Valery V.

In: Macromolecules, Vol. 38, No. 9, 03.05.2005, p. 3663-3678.

Research output: Contribution to journalArticle

Malkoch, M, Schleicher, K, Drockenmuller, E, Hawker, CJ, Russell, TP, Wu, P & Fokin, VV 2005, 'Structurally diverse dendritic libraries: A highly efficient functionalization approach using click chemistry', Macromolecules, vol. 38, no. 9, pp. 3663-3678. https://doi.org/10.1021/ma047657f
Malkoch M, Schleicher K, Drockenmuller E, Hawker CJ, Russell TP, Wu P et al. Structurally diverse dendritic libraries: A highly efficient functionalization approach using click chemistry. Macromolecules. 2005 May 3;38(9):3663-3678. https://doi.org/10.1021/ma047657f
Malkoch, Michael ; Schleicher, Kristin ; Drockenmuller, Eric ; Hawker, Craig J. ; Russell, Thomas P. ; Wu, Peng ; Fokin, Valery V. / Structurally diverse dendritic libraries : A highly efficient functionalization approach using click chemistry. In: Macromolecules. 2005 ; Vol. 38, No. 9. pp. 3663-3678.
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