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

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 cocrystal 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-HMIDLINE HORIZONTAL ELLIPSISO, hydrogen bonds and C-HMIDLINE HORIZONTAL ELLIPSIS pi interactions. Interestingly, jellyfish like architecture is obtained by the interaction of PPPA with R4A molecules through collaborative C-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSISN and O-HMIDLINE HORIZONTAL ELLIPSISN 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.

Automated summary

In recent years, the collaboration of macrocyclic chemistry and co-crystal engineering has rapidly advanced for the creation of functional solid-state materials. In this study, a novel jellyfish-like co-crystal structure was constructed by precise engineering of supramolecular interactions, guiding future endeavors in the design of supramolecular interactions and development of promising novel functional materials.