Formation of Interesting Organic Supramolecular Structures in the Solid-State Self-Assembly of Triphenol Adducts

Abstract

Utilization of the interplay of dimensionality (1D, 2D, 3D), orientation of functional groups of the building blocks, influence of rigid/flexible linking groups, and weak interactions provides an interesting route for the creation of novel supramolecular architectures in the crystal lattice. Molecular complexes of triphenol 1 with aza compounds such as pyrazine (pyz), 1,10-phenanthroline (phen), 4,4′-bipyridyl (bpy), trans-1,2-bis(4-pyridyl)ethylene (bpy-ethe), and 1,2-bis(4-pyridyl)ethane (bpy-etha) have been investigated using X-ray diffraction techniques. The rigid 3D triphenol 1 self-assembles to form a distorted ladder, which organizes into columns via O-H‚‚‚O hydrogen bonds. Self-assembly of complexes 1‚pyz and 1‚bpy-ethe result in ladder-type structures with pyz and bpy-ethe molecules forming the rungs of the ladder. The molecular components in complex 1‚phen aggregate into 1D hydrogenbonded chains. A 4-fold self-clathration was observed in the crystal lattice of 1‚bpy. Owing to the expanded lattice of the complex 1‚bpy-etha, one of the reactant molecules of bpy-etha fills the spaces as guest molecules. The nature of the aza groups helps to enhance the overall volume of the crystal lattice thus leading to the formation of various supramolecular assemblies.

Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide

“…Further, it is noted that syn and anti forms of a closely related molecule, 4-[2-(pyridin-4-yl)ethyl]pyridine, are found within the same crystal structure, i.e. in its 1:1 co-crystal with bis(2-hydroxyphenyl)-4-hydroxyphenylmethane [54]. Finally, it is noted that 2 was isolated from a failed co-crystallisation experiment.…”

Multicomponent Crystal Systems of Known Antimalarial Drug Molecules

“…However, using ab initio calculations, Vishweshwar and co‐workers found that the acid–amide heterosynthon (b) is more favourable than the acid–acid homosynthon. Others, such as the amide homosynthon (c) and the acid–pyridine (d) heterosynthon are also widely studied in crystal engineering …”

Supramolecular Organic Frameworks of Brominated Bisphenol Derivatives with Organoamines

“…At the same time, notwithstanding their weak bonding and angular spreading pattern, H-bonds have been approved as directional and predictive intermolecular cohesive forces in molecular packing . Among others, H-bonds as main driving forces in supramolecular assemblies of organic modules featuring functional carboxyl, pyridyl, or a mixture of the two have been comprehensively explored. ,,,,,,, It should also be noted that phenol–amine interplay has been confirmed to be a type of stable and robust driving forces for the exploitation of new solid materials, and the well-defined O–H···N bonds furnished in molecular compounds have been found productive for the generation of a wide variety of supramolecular aggregates . During the course of our investigations in crystal engineering of phenol–amine salts and adducts, we recently discovered that halogenations of bis(4–hydroxyphenyl)sulfone (BPS) would boost the abilities of the functional phenols to form H-bonds in directing molecular assembly and recognition .…”