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)