Novel jellyfish-shaped resorcin[4]arene macrocyclic cocrystal via collaboration of macrocyclic chemistry and co-crystal engineering: Insight into structural, noncovalent interactions and computational chemistry

• Published in: Journal of molecular structure Vol. 1298; p. 137034
• Main Authors: Khan, Arshad, Bushnak, Ibraheem, Jiang, Zhouyu, Usman, Rabia, Choudhari, Prafulla B., Feng, Chao, Al-Kaysi, Rabih O., Rahman, Faiz-Ur
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-02-2024
• Subjects: Cocrystal; DFT; FTIR; Resorcinarenes; SCXRD; Stilbene; DFT; SCXRD; Cocrystal; FTIR; Resorcinarenes; Stilbene
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.137034

•A novel jellyfish shaped organic cocrystal RMC was synthesized by a slow evaporation method.•The cocrystal was characterized by single crystal X-ray diffraction and, XRD and infrared spectroscopy.•Hydrogen bonding (C–H⋯O and C–H⋯N) interactions play a crucial role in stabilizing various supramolecular architectures of the title complexes in the solid state.•In complex RMC, the acetone is involved in the formation of a linear acetone−R4 architecture stabilized by hydrogen bonds and CH⋯π interactions.•DFT and Hirshfeld analysis used to study the role of different interactions.
The collaboration of macrocyclic chemistry and co-crystal engineering has witnessed rapid development in recent years for the creation of functional solid-state. Here, we report the construction of novel jellyfish-like co-crystal derived from macrocyclic resorcin[4]arenes (R4A) serving as a bell and (Z)-3-(pyridine-4-yl)-2-(4-(pyridine-4-yl)phenyl)acrylonitrile (PPPA) molecules acting as a tentacle through the precise engineering of supramolecular interactions. The co-crystal structure was comprehensively investigated using single crystal X-ray diffraction (SXRD), X-ray powder diffraction (XRD), Infrared spectroscopy (IR) and molecular modeling. The packing pattern of the co-crystal structure shows the inclusion-of acetone solvent that connects the neighboring R4A cavitands into high order linear structure stabilized by multiple C–H⋯O, hydrogen bonds and C–H⋯π interactions. Interestingly, jellyfish like architecture is obtained by the interaction of PPPA with R4A molecules through collaborative C–H⋯O, CH⋯N and OH⋯N Hydrogen bonds. Additionally, the HOMO-LUMO, molecular electrostatic potential (MESP), Interaction region indicator (IRI) analysis, and Localized orbital locator (LOL) were collectively employed to provide comprehensive insights into the electronic structure and reactivity of the studied compound. Hirshfeld surface analysis in combination with 2D fingerprints plots were carried out to get insight into the role of various non-covalent routs in the formation cocrystal packing. This strategy will guide any future synthetic endeavors aimed at engineering supramolecular interactions on demand using macrocycle chemistry and co-crystal engineering for the development of promising novel functional materials.