Symmetry of Pyridine Derivatives Controlled Two-Dimensional Nanostructural Diversity by Co-Assembly with Aromatic Carboxylic Acids

The self-assembly behaviors of aromatic carboxylic acids are commonly investigated at the liquid/solid interfaces because of their rigid skeletons and both hydrogen-bond donors and receptors. However, self-assemblies of aromatic carboxylic acids with low symmetry and interactions between carboxylic acid and pyridine derivatives are worth exploring. In this work, the self-assembled structural transitions of a kind of low-symmetric aromatic carboxylic acid (H4QDA) are regulated by the coadsorption of two pyridine derivatives (DPE and T4PT) with different symmetry, which are investigated by scanning tunneling microscopy under ambient conditions. For the H4QDA/DPE system, the grid structure appears. For the H4QDA/T4PT system, the coassembled morphologies display an obvious concentration dependence. With the increase of solution concentration of T4PT, three coassembled patterns (network structure, chiral linear structure, and brick-like structure) are observed. Corresponding structural models suggest that the O–H···N hydrogen bonds have great contributions to stabilizing these coassembled structures. Our studies will help to explore the complexity, diversity, and functionality of multiple component systems and are conducive to further understanding the underlying mechanisms in the assembly process.