4-[4-(1<i>H</i>-Imidazol-4-yl)phenyl]-1<i>H</i>-imidazole

Wang, Qian; Zhao, Xiao‐Li

doi:10.1107/s1600536812032485

Cited by 2 publications

(3 citation statements)

References 6 publications

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“…Theoretical analysis of the intermolecular interactions pattern was performed within the Bader’s Quantum Theory of Atoms in Molecules (QTAIM) , supplemented with reduced density gradient (RDG) technique. Within the QTAIM approach, the electron density distribution ρ( r ) is treated as a scalar field and examined by analysis of the accompanying gradient ∇ρ( r ) vector field.…”

Section: Methodsmentioning

confidence: 99%

“…If flat, DPI4B can be a promising alternative to the above compound. To study this effect apart from newly synthesized DPI4B (proportion of homocyclic and heterocyclic rings 3:2), three related compounds 2-phenyl-1 H -imidazole (2PI) (proportion 1:1), 4-phenyl-1 H -imidazole (4PI) (proportion 1:1), and 1,4-di(1 H -imidazol-4-yl)benzene (DI4B) (proportion 1:2) (Figure ) were selected. Both 2PI and 4PI were identified as moieties, which can be easily found in DPI4B as molecular fragments.…”

Section: Introductionmentioning

confidence: 99%

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Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component

Latosińska

Maurin

et al. 2015

Crystal Growth & Design

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The crystal structure of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene (DPI4B) is determined by X-ray diffraction with a final R-factor of 6.42% at room temperature. It crystallizes with a space group P2 1 /c, Z = 4, a = 5.01790(10), b = 28.8971(6), and c = 12.9362(3) Å; β = 98.757(2)°. Two 4-phenyl-1H-imidazole (4PI) fragments are related by inversion symmetry and each makes a dihedral angle of 0°with the benzene rings. Despite the presence of a total number of five homo-and heterocyclic rings in the DPI4B molecule, similarly to 2-phenyl-1H-imidazole (2PI) but in contrast to 1,4-di(1H-imidazol-4-yl)benzene (DI4B) and 4-phenyl-1H-imidazole (4PI), it is almost planar. Each plane containing a terminal phenyl ring makes a small dihedral angle of about 3°with the central benzene ring plane. The average twisting angle of the whole molecule is equal to 7°. The ordering of compounds studied according to the decreasing twisting angle is 4PI > DI4B > DPI4B > 2PI and is the same as that according to hydrogen bond length/strength. In DPI4B bereft of N−H···N bonds, four weak C−H···N bonds of C···N = 3.362 Å and ∠(C, H, N) = 158°; C···N = 3.437 Å and ∠(C, H, N) = 123°; C···N = 3.392 Å and ∠(C, H, N) = 128°and C···N = 3.914 Å and ∠(C, H, N) = 156°, force crystalline packing with almost perpendicular adjacent molecules. Strong π···π stacking allows dense packing of planar array of molecules, with a small interlayer distance of 3.413 Å. The analysis of intermolecular interactions pattern supported by quantum theory of atoms in molecules (QTAIM), reduced density gradient (RDS), and Hirshfeld surfaces approach reveals subtle and diverse types of interactions difficult to describe within standard techniques. QTAIM/Hirshfeld clearly indicate the role of interplay between C−H···N hydrogen bonds, N···π and π···π stacking, and a shift from strong (N−H···N) to very weak (C−H···N) attractive interactions supplemented by π···π displaced pure type stacking upon aromatic ring count. QTAIM/RDS reveal mixed attractive/repulsion interactions forcing flatness of the molecule. Electrostatic potential indicates the complementarity of the regions bonded through the C−H···N in the neighboring molecules, which permits easy overcome of any repulsive interactions in DPI4B that may destroy the flatness of the molecule.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component

Latosińska

Maurin

et al. 2015

Crystal Growth & Design

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“…According to earlier structural studies on several similar bisimidazoles exemplified in Chart , coplanar and straight (symmetric) connection is often accompanied by symmetric locations of NH hydrogen atoms, so that the electric polarities of the two imidazolyl units cancel one another out. The molecular structures are symmetric and nonpolar for 1 H ,1′ H -2,2′-biimidazole (Bim), 1 H ,1′ H -2,2′-bibenzimidazole (BBI), several 1 H ,1′ H -4,4′-biimidazole derivatives (R2-44Bim; R = H, Me, Et), − and two p -phenylene-bridged derivatives ( s -44Im2P and s -BI2P , ), whereas the o -phenylene- or methylene-bridged imidazoles Im2P and 44Im2C retain their polarity as a result of twisting of the two imidazolyl rings. The bridging spacers selected in the present study were o -phenylene (BI2P ( 1 ), TMBI2P ( 2 ), and BI2X ( 3 )), thien-2,5-diyl (BI2T ( 4 ) and TMBI2T ( 5 )), and 1 H -imidazole-4,5-diyl units (BI2Im ( 6 ), TMBI2Im ( 7 ), BI2MIm ( 8 ), and TMBI2MIm ( 9 )), which are expected to be bent, so as to eliminate inversion symmetry.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-Bonded Architectures and Field-Induced Polarization Switching in Bridged Bis(benzimidazole) Crystals

Horiuchi

Ishibashi

Inada³

et al. 2018

Crystal Growth & Design

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The imidazole ring is chemically stable and forms an excellent building block for compounds that show externally switchable polarization in their crystalline states. We examined the structural properties of nine bridged bis-(benzimidazole)s, of which seven were new compounds, in an attempt to identify substances with highly polarizable dielectric properties arising from the multistability of their polar supramolecular architectures. Selected bridging ophenylene, thien-2,5-diyl, or 1H-imidazole-4,5-diyl units improved the thermal robustness as expected. Solution evaporation or vacuum sublimation of the bridged bis-(benzimidazole)s afforded single crystals, with or without solvent molecules, in which the molecules were hydrogen bonded to form either extended ribbons or cyclic oligomeric structures. 2,2′-(1,2-Phenylene)bis-1H-benzimidazole (BI2P) formed ladder-like ribbons that exist as low-or high-dipole configurations depending on the parallel or antiparallel orientation of the NH hydrogen atoms between the two benzimidazole rings. These two configurations were nearly degenerate in stability, permitting them to be electrically switched, as evidenced by their double (P−E) hysteresis curves. The switching process was ascribed to an order−disorder-type paraelectric-to-ferroelectric phase transition rather than to an antiferroelectric-toferroelectric phase transition. BI2P is also unique as a paraelectric crystal in which the ferroelectric state is field induced but is unexpectedly inaccessible by exclusively thermal stimulation.

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4-[4-(1H-Imidazol-4-yl)phenyl]-1H-imidazole

Cited by 2 publications

References 6 publications

Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component

Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component

Hydrogen-Bonded Architectures and Field-Induced Polarization Switching in Bridged Bis(benzimidazole) Crystals

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