Tuning of a Hydrogen-Bonded Organic Framework by Liquid-Assisted Mechanosynthesis between Trans-Aconitic Acid and Isonicotinamide

Abstract

Cocrystallization of trans-aconitic acid (TACA) and isonicotinamide (INA) using liquid assisted mechanochemical grinding results in a unique supramolecular hydrogen-bonded organic framework (HOF) system encapsulating various organic solvents (liquid guest) with the formation of channel inclusion compounds. Dimension and shape of the framework is dependent on the solvent used during liquid assisted grinding (LAG). Although crystal structure of the cocrystal (TACA) ⋅ (INA)2 ⋅ (H2O)@(INA)0.5 has been determined by Single Crystal X-ray diffraction (SCXRD), crystal structures of 3 cocrystal HOFs were determined by microcrystal electron diffraction (MicroED) and synchrotron X-ray diffraction due to lack of suitable single crystal. PXRD analysis confirms isostructurality of various host-guest systems; whereas guest incorporation as well as stability of the HOFs were further confirmed using thermogravimetric analysis. This study demonstrates that the framework of HOFs can be tuned by varying solvent molecules used during LAG.