Figure 2. Aggregation modes of the both molecules in their solid phases with the noncovalent interactions.
The molecule AB1 demonstrates stacking columns along the c-axis where the molecules adopt a slipped antiparallel face-to-face (H type) packing style [Cg2Cg1; Cg1: N1-N2-C2/C4, Cg2:C6/C11, symmetry code:1/2-x,-1/2+y,1/2-z for 3.68, 1/2-x,1/2+y,1/2-z for 3.74 ] which have shifting along the long and short molecular axis (roll distance (dr): 1.53 ; pitch distance (dp):0.22) and an interplanar distance of 3.68 and 3.74 with the slipping angle of 19.5˚ (Figure 2 ). The molecule AB2 packs in antiparallel displaced stacking modes ( J type) [Cg2Cg2; Cg2:C6/C11, symmetry code:2-x,1-y,1-z] in its crystals structure and the molecule is replaced mostly along the long molecular axis with an interplanar distance of 5.002 (Figure 2) with the slipping angle of 45.5 ˚. When the interplanar distance is 4.10 between the adjacent rings of the AB2 [ Cg2Cg2; Cg2:C6/C11, symmetry code:1-x,1-y,1-z], its aggregation mode behaves nearly antiparallel H type stacking mode with the small slipping angle of 20.4˚. These two stacking modes of the AB2 demonstrate the charge pathways in its solid phase. Therefore, the attaching of these substitution groups leads to striking changes in molecular aggregation. Small perpendicular distance with the J type and antiparallel H type stacking modes is desired property for the high charge transfer rate[2, 57, 58]. In addition, the rigidity of the molecules in solid state increases the charge transport which arise from restricted intra-intermolecular rotation process (RIR). The RIR process is created by the noncovalent interaction observed in the both molecules. According to SCXRD results, It is predicted that this series of pyrzazole derivatives can be good candidate for ambipolar semiconducting materials when they are used as a device in real world since they have favourable strong stacking modes (J and H type)