Construction of Hydrogen-bonded Crystalline Frameworks Using Tetrakis(carboxyphenyl)dimethyldihydropyrene Derivative

Abstract

A new building block molecule, 4,5,9,10-tetrakis(4-carboxyphenyl)dimethyldihydropyrene derivative CP-DHP was synthesized and applied for construction of hydrogen-bonded organic frameworks (HOFs). Although methyl groups standing on the center of the [14]annulene ring prevent π/π stacking between the rings, we revealed that layered assemble structures of H-bonded two-dimensional sheets were formed under the optimized crystallization condition. Additionally, we found that the stacking manner altered depending on aromatic template molecules. We synthesized and crystallized 4,5,9,10-tetrakis(4-carboxyphenyl)dimethyldihydropyrene derivative CP-DHP to construct hydrogen-bonded organic frameworks (HOFs). Although methyl groups standing on the center of the [14]annulene ring prevent π/π stacking between the rings, layered assemble structures of H-bonded two-dimensional sheets were formed under the optimized crystallization condition. The stacking manner altered depending on aromatic template molecules.