This thesis provides an overview of the key findings in a thesis. It discusses the synthesis of squaramates and squaramides with varying alkyl chain lengths, primarily for foldamer formation. However, intermolecular interactions in the crystal structures led to open molecular structures. Unique crystal packing was observed in different cases. The crystal structures revealed catemers with N–H ···O hydrogen bonding and π-stacking. Some cases also exhibited H ···H bonding. The relationship between crystal structure and mechanical properties was explored using nanoindentation, showing exceptional properties for specific squaramates and squaramides due to crystal packing. Anion binding capabilities of phenyl alkyl squaramides were investigated through spectroscopic methods. Macrocyclic squaramides were synthesized using lysine but didn't yield desired results in anion encapsulation.