Two Unexpected Temperature-Induced Supermolecular Isomers from Multi-Topic Carboxylic Acid: Hydrogen Bonding Layer or Helix Tube

Abstract

Under ambient conditions or 160 °C, two supramolecular isomers, namely [(H4PTTA)(H2O)2(DMF)] and [(H4PTTA)(H2O)3]··Guest (1-L and 1-H, H4PTTA = N-phenyl-N′-phenyl bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxdiimide tetra-carboxylic acid, Guest = DMF and H2O), were obtained through the reaction of H4PTTA in a mixture of H2O and dimethylformamide. The single crystal structures reveal the temperature-dependent supramolecular isomerism derived from the torsion of semi-rigid of H4PTTA. The 1-L prepared at room temperature is a hydrogen bond based achiral layer, while the hydrothermal synthesized 1-H is isomer resulted in an H-bond-based chiral tubes-packed supramolecular framework.

Synthesis, Crystal Growth, Structural Characterization, Supramolecular Chemistry, and Theoretical Calculations of Methylenium Salts of Benzenesulfonates

“…The various synthetic strategies such as electrostatic interactions, hydrogen bonding, halogen bonding and π‐interactions have generally been utilized in the production of these purely organic supramolecular structures [6–8] . Hydrogen bonds play crucial function in crystal engineering because of their selectivity and directionality in controlling molecular aggregation, which defines the properties of materials [9–14] . The investigation of interactions between various functional groups (e. g. supramolecular synthons capable of developing strong hydrogen bonds), is essential for the expected design of solid‐state assemblies [15–17] .…”

“…[6][7][8] Hydrogen bonds play crucial function in crystal engineering because of their selectivity and directionality in controlling molecular aggregation, which defines the properties of materials. [9][10][11][12][13][14] The investigation of interactions between various functional groups (e. g. supramolecular synthons capable of developing strong hydro-gen bonds), is essential for the expected design of solid-state assemblies. [15][16][17] In this scenario, conventional XÀ HÀ X (X=N, O, F, Cl) hydrogen bonds established between two neutral groups, have played a dominant role in the past decades.…”