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

Abstract

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

Crosslinking of viral nanoparticles with “clickable” fluorescent crosslinkers at the interface

“…Of all the reactions that can be ranked under click chemistry, Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction is undoubtedly the premier example of all [4,5]. This reaction has been extensively used in materials development [6][7][8][9], polymer synthesis [10,11], dendrimer synthesis [12][13][14][15][16] and drug discovery [17][18][19]. CuAAC reaction serves as a great tool for bioconjugation applications [20][21][22][23][24][25][26][27][28][29], mainly due to (i) facile synthesis and easy incorporation of alkyne and azide moieties into biomolecular frameworks, (ii) compatibility to other functionalities yielding highly specific products, (iii) compatibility to water which is crucial for biomolecular systems, (iv) mild reaction conditions which will help maintaining the properties of biomolecules, and (v) stability of the resulting triazole ring to the hydrolytic cleavage, oxidation and reduction [2,3,9].…”

Synthesis and characterization of novel polytriazoleimides by CuAAC step-growth polymerization

“…[26][27][28] However, 1,2,3-triazole compounds have a good affinity for metallic surfaces and are far more stable than 1,2,4-triazole compounds to attack by other chemical entities. 29,30 We therefore believe that polyimide materials with new molecular structures based on 1,2,3-triazole may have advantageous properties for high-performance metal coatings and adhesives.…”

Synthesis and Characteristic of Novel Soluble Triazoleimide Oligomers with Terminated Arylacetylene

“…Sharpless, Fokin, and Finn combined di-, tri-, and tetravalent azides and alkynes to produce crosslinked polymers as adhesives, which could bind metal surfaces together. 15 The triazole's electronic properties have made it popular among fluorgenic probes. Fahrni and Wang both demonstrated a dye that exhibited no fluorescene until click chemistry was performed to yield a triazole moiety.…”