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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.
Highlights
Crystal engineering, traced since 1955 and accelerated in the 1980’s by the independent efforts of Desiraju and other chemists, was further expanded as a fruitful research field encompassing various domains of chemistry, biology, pharmaceuticals and materials science [1,2,3,4,5]
The prototypal organic networks of carboxylic acid systems are usually formed through the well-known R22(8) eight-member carboxylic acid hydrogen bond dimers, which are considered as the concepts of supramolecular synthons [15]
Within the H4TPPA molecule, there are two types of strong hydrogen bond motifs: R22(8) eight-member dimeric carboxylic homosynthon and one water inserted ten-member heterosynthon (Figure 1a)
Summary
Crystal engineering, traced since 1955 and accelerated in the 1980’s by the independent efforts of Desiraju and other chemists, was further expanded as a fruitful research field encompassing various domains of chemistry, biology, pharmaceuticals and materials science [1,2,3,4,5]. Expected of co-crystals, the supramolecular isomerism, which comprises different structural networks derived from identical chemical compositions, is attracting considerable investigative attentions. It is difficult and a great challenge to accurately predict or control the final supramolecular isomeric structures, owing to the subtle perturbation existence of thermodynamic and kinetic factors in the self-assembly process, such as different formation energy, building units’ variation or intermolecular interactions. We report two multitopic carboxylic acid-based isomers, where the solvent water molecules of solvation are incorporated, acting as the spacer characters to tune the homosynthon to heterosynthon, while being led to form the achiral layer at ambient or chiral tube at high temperature, respectively. After autoclave cooling to room temperature at a rate of 5 ◦C·h−1, colorless block crystals were isolated
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