Within this master thesis the imines were prepared through condensation of o-vanillin (ov) and amines (3- and 4-aminoacetophenone and 2-aminonaphtalene, 3aa, 4aa and 2an, respectively). The possibility of cocrystallization of the imines and six halogen bond donors: 1,2- and 1,4-diiodotetrafluorobenzene (1,2-tfib and 1,4-tfib), 1,4-dibromotetrafluorobenzene (1,4-tfbb), iodopentafluorobenzene (ipb), N-bromosuccinimide (NBS) and N-bromophtalimide (NBF), was investigated by means of mechanochemical synthesis and crystalization from solution. The crystals were described by powder X-ray diffraction and differential scanning calorimetry. The crystal and molecular structures of three prepared cocrystals with perfluorinated halogen bond donors and two polymorphs of an imine bromination and cyclization product were explored by single crystal X-ray diffraction. In all cocrystals, the donor molecules are ditopic and connected to the imine molecules via IO halogen bonds. In the cocrystal (ov3aa)2(1,4-tfib) the acceptors of halogen bonds are the carbonyl groups of ov3aa molecules and in (ov2an)2(1,4-tfib) the 1,4-tfib molecules are bifurcatedly connected to hydroxy and methoxy groups of the ov2an molecule. In (ov4aa)(1,2-tfib) the 1,2-tfib molecules are connected bifurcatedly to hydroxy and methoxy groups of one ov4aa molecule and monofurcatedly to the carbonyl group of the other imine molecule. synthesis.