Squaramides are a family of compounds based on a cyclobutenedione ring with two directly bonded amino groups. This molecular configuration confers them versatile non-covalent interaction possibilities by means of hydrogen bonds, dipolar interactions and π-π stacking. Accordingly, squaramide derivatives have been increasingly used in supramolecular chemistry to develop molecular receptors and sensors, catalysts, and more recently supramolecular polymers and gels. Our research focuses on the study of the self-assembly patterns of squaramide units and its capacity to generate pathway complexity and supramolecular polymorphism. On the one hand, we developed a new macrocycle self-assembling via hydrogen bonds into two different polymorphs depending on the Z,E conformation of the squaramide units. On the other hand, we prepared a family of amphiphilic aryl-squaramides that aggregate in water via uncommon dipolar π-π interactions, while no hydrogen bonds are formed. These latter compounds have been applied for the preparation of thixotropic hydrogels for the controlled release of zwitterions. We believe that the versatility of squaramides to form supramolecular aggregates through different interactions makes them interesting compounds for the development of novel supramolecular materials.

Squaramides as versatile binding units for the development of supramolecular polymers

ACS Fall 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.