Morphological Control of Guanidinium‐Oxyanion Supramolecular Polymers

Morphology plays a central role in determining the bulk properties of supramolecular materials. We report here a series of small molecule‐derived supramolecular polymers based on charge‐assisted hydrogen bonding interactions of a bis(guanidine) with varying ratios of difunctional carboxylic and sulfonic acids. Multiple orthogonal characterization methods indicate that the materials' properties exist on a spectrum from amorphous pressure‐sensitive adhesives to semicrystalline thermoplastics, and behavior is largely dependent on the amount of rigid, crystallizable bis(sulfonic acid) present. Furthermore, we show that adhesive behavior can be tuned based on the size of the dicarboxylic acid and that the materials can be reprocessed multiple times with minimal changes in their mechanical properties.