Supramolecular Organogels Prepared from Pillar[5]arene-Functionalized Conjugated Polymers

Supramolecular polymeric networks are capable of producing gels that exhibit stimulus responsive, self-healing properties and are useful in a variety of applications. In this work, a pillar[5]arene derivative bearing a single azide functionality was prepared and coupled via strain-promoted azide–alkyne cycloaddition chemistry to a conjugated polyimine consisting of dibenzocyclooctyne units in its backbone. The resulting polypillar[5]arene structure was found to form inclusion complexes with cyanoalkanes and produced organogels when mixed with cyanoalkyl-functionalized polymers. The resulting gels could be hydrolyzed by exposure to acid and could subsequently be regenerated by dehydration. In addition, these organogels exhibited self-healing behavior if severed and reconnected.