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One-pot mechanosynthesis of halogen bonded cocrystals from o-vanillin imines and perfluorinated compounds

Classic mechanochemical synthesis of o-hydroxy imine cocrystals with perfluorinated aromatic halogen bond donors was described previously and it comprises a stepwise procedure of the synthesis of imine from an aldehyde and amine followed by cocrystallization [1]. Herein we report imines derived from o-vanillin (ov) and two amines, benzylamine (bam) and 1-adamantylamine (adm) having a hydroxyl and a methoxyl group which can act as halogen bond acceptor sites. The main perspective of this work was to obtain cocrystals of the prepared imines with perfluorinated compounds: 1, 2-, 1, 3- and 1, 4- diiodotetrafluorobenzene (12tfib, 13tfib and 14tfib) as well as 1, 3, 5-triiodotrifluorobenzene (135tfib) as halogen bond donors. Using ov, bam or adm and the donors in various stoichiometric ratios we have prepared cocrystals by one-pot mechanosynthesis simultaneously forming covalent and supramolecular (halogen) bonds [2]. All reactants and products were characterized by means of PXRD. The mechanochemical experiments were accompanied by crystallization. [1] M. Zbačnik, M. Vitković, V. Vulić, I. Nogalo, D. Cinčić, Cryst. Growth Des. 16 (2016) 6381. [2] D. Cinčić, T. Friščić, CrystEngComm 16 (2014) 10169.

cocrystals, crystallization, halogen bonding, mechanochemistry, one-pot synthesis

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