Structurally Diverse Dendritic Libraries:  A Highly Efficient Functionalization Approach Using Click Chemistry

• Published in: Macromolecules 2005-05, Vol.38 (9), p.3663-3678
• Main Authors: Malkoch, Michael, Schleicher, Kristin, Drockenmuller, Eric, Hawker, Craig J, Russell, Thomas P, Wu, Peng, Fokin, Valery V
• Format: Article
• Language: English
• Subjects: Applied sciences; architecture; building-blocks; copper(i)-catalyzed azide-alkyne; cycloaddition; dendrons; ether) dendrimers; Exact sciences and technology; macromolecules; Organic polymers; physical-properties; Physicochemistry of polymers; polymers; Polymers with particular structures; Preparation, kinetics, thermodynamics, mechanism and catalysts; terminal groups
• ISSN: 0024-9297; 1520-5835; 1520-5835
• DOI: 10.1021/ma047657f

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.