Hydrogen-bonded networks of 2,2′-substituted 4,4′-biimidazoles: New ligands for the assembled metal complexes

Murata, Tsuyoshi; Yoshie, Naoko; Nakasuji, Kazuhiro

doi:10.1016/j.poly.2005.03.147

Cited by 13 publications

(5 citation statements)

References 24 publications

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“…2,2'-Biimidazole was purc h a s e d f r o m S a n t a C r u z B i o t e c h n o l o g y, I n c . 2-( P y r i d i n e -2-y l ) -i m i d a z o [1,2-a ] p y r i d i n e 37) , 1-(pyridine-2-yl)imidazo[1,5-a]pyridine 38) , 3-(pyridine-2-yl)-imidazo[1,5-a]pyridine 39) , 4,4'-biimidazole 40), 41) , 1,1'-dimethyl-2,2'-biimidazole 42) , and [IrCp (H2O)3] [SO4] 43) were synthesized according to the respective literature procedures . Complexes 1a-b, 3, 4, 6, 10, and 12 were synthesized according to the literature 34) .…”

Section: Methodsmentioning

confidence: 99%

Iridium Catalysts with Diazole-containing Ligands for Hydrogen Generation by Formic Acid Dehydrogenation

Manaka

Onishi

Iguchi

et al. 2017

J. Jpn. Petrol. Inst.

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Section: Methodsmentioning

confidence: 99%

Iridium Catalysts with Diazole-containing Ligands for Hydrogen Generation by Formic Acid Dehydrogenation

Manaka

Onishi

Iguchi

et al. 2017

J. Jpn. Petrol. Inst.

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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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“…Using our protocol, biimidazole ligand 17 was synthesized in three steps. The literature method to synthesize 17 involved a linear five-step reaction using the same starting material, 2-ethylimidazole …”

mentioning

confidence: 99%

“…The literature method to synthesize 17 involved a linear five-step reaction using the same starting material, 2-ethylimidazole. 50 …”

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confidence: 99%

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Dehydrogenative Syntheses of Biazoles via a “Pre-Join” Approach

Wang

Dong

et al. 2023

JACS Au

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The structural motif of biazoles is the predominant substructure of many natural products, pharmaceuticals, and organic materials. Considerable efforts have focused on synthesizing these compounds; however, a limited number of processes have been reported for the efficient formation of biazoles. Herein, we report a "pre-join" approach for the dehydrogenative synthesis of biazoles, which are challenging to prepare using conventional methods. A bench-stable and easily synthesized pyrazine-based group is critical for this transformation. This strategy enables the homocoupling of biazoles and the heterocoupling of two different azoles. Due to the broad substrate scope, this strategy exhibits potential for use in other fields, such as medicine, materials, and natural product chemistry.

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Hydrogen-bonded networks of 2,2′-substituted 4,4′-biimidazoles: New ligands for the assembled metal complexes

Cited by 13 publications

References 24 publications

Iridium Catalysts with Diazole-containing Ligands for Hydrogen Generation by Formic Acid Dehydrogenation

Iridium Catalysts with Diazole-containing Ligands for Hydrogen Generation by Formic Acid Dehydrogenation

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

Dehydrogenative Syntheses of Biazoles via a “Pre-Join” Approach

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