The use of strain-promoted azide-alkyne cycloaddition (SPAAC) chemistry has attracted significant attention due to its mild reaction conditions, orthogonality, and rapid reactivity. This synthetic strategy has been extensively used in bioconjugation chemistry, and in the development of some biomaterials. Despite their utility, the use of strained cyclooctynes has found few applications in polymer and materials chemistry. Recently, we reported the synthesis of a diamine derivative of dibenzocyclooctyne (DIBO-NH<sub>2</sub>) and its Schiff-base polymerization with a dialdehyde co-monomer, which resulted in a DIBO-containing conjugated polyimine. This novel structure was found to exhibit a high degree of reactivity toward various azide derivatives, and can serve as a precursor for the preparation of numerous triazole derivatives. We have elaborated this material to the preparation of polymers bearing pillar[5]arenes and a variety of other side-chains, and have investigated these polymers as building blocks for supramolecular gels and as carbon nanotube dispersing agents that enable formation of novel reactive nanocomposites. In addition, we have used dibenzocyclooctynes as components of non-conjugated polymers, and have developed entirely new polymer structures using SPAAC chemistry. The synthesis of these structures is extremely simple, only requiring evaporation of solvent at ambient temperature over the course of several minutes in order to produce high molecular weight polymeric species.

Strain-promoted cycloadditions for the synthesis and functionalization of polymers and nanocomposites

2019 Spring National Meeting

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