Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2004-09, Vol.42 (17), p.4392-4403
• Main Authors: Díaz, David D., Punna, Sreenivas, Holzer, Philipp, McPherson, Andrew K., Sharpless, K. Barry, Fokin, Valery V., Finn, M. G.
• Format: Article
• Language: English
• Subjects: adhesives; alkynes; Applied sciences; azides; click chemistry; copper; cycloaddition; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; transition metal chemistry
• ISSN: 0887-624X; 1099-0518
• DOI: 10.1002/pola.20330

The copper(I)‐catalyzed cycloaddition reaction between azides and alkynes has been employed to make metal‐adhesive materials. Copper and brass surfaces supply the necessary catalytic Cu ions, and thus the polymerization process occurs selectively on these metals in the absence of added catalysts. Alternatively, copper compounds can be added to monomer mixtures and then introduced to reducing metal surfaces such as zinc to initiate polymerization. The resulting materials were found to possess comparable or superior adhesive strength to standard commercial glues, and structure‐activity correlations have identified several important properties of the monomers. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4392–4403, 2004 A sticky situation is observed when polyvalent azides and alkynes are assembled into crosslinked polymer networks by copper‐catalyzed 1,3‐dipolar cycloaddition. The condensation polymerization is efficiently promoted by Cu ions either leached from the metal surface or added to the monomer mixture, and strong interactions with metal surfaces are provided by the multiple triazole binding elements produced.