Hydrogen Bonding Control of Molecular Self-Assembly: Aggregation Behavior of Acylaminopyridine–Carboxylic Acid Derivatives in Solution and the Solid State

In this paper we report the design, synthesis and investigation of a family of acylaminopyridine–carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs.