Structure and isomerization in 4,4′-biimidazoles: a comparison of crystal structures and theoretical calculations of 2,2′-dimethyl-4,4′-biimidazole and 2,2′-dimethyl-4,4′-biimidazolium bis-trifluoroactate

Zhang, Weidong; Landee, Christopher P.; Willett, Roger D.; Turnbull, Mark M.

doi:10.1016/s0040-4020(03)00987-6

Cited by 10 publications

(3 citation statements)

References 19 publications

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“…In the CT salts with TCNQ radical anion, such a feature of the H-bond directionality of 4,4′-H 2 Bim regulated the orientation of TCNQ molecules and significantly affected the transport properties to give highly conductive CT salts . Furthermore, our synthetic studies on chemical modifications of 4,4′-H 2 Bim systems such as introduction of alkyl substituents, insertion of a π-electronic system, and oligomerization have demonstrated an increase in the variation of H-bond directionalities and network structures in their crystal structures.…”

Section: Introductionmentioning

confidence: 88%

Hydrogen-Bond Architectures of Protonated 4,4′-Biimidazolium Derivatives and Oligo(imidazolium)s in Charge-Transfer Salts with Tetracyanoquinodimethane

Murata

Yakiyama

Yamamoto

et al. 2008

Crystal Growth & Design

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Charge-transfer salts of protonated cations of 2,2′-disubstituted-4,4′-biimidazoles and oligo(imidazole)s with tetracyanoquinodimethane (TCNQ) were investigated to demonstrate the high potential of these systems for the regulation of molecular arrangement and electronic structure of charge-transfer salts. 4,4′-Biimidazole derivatives afforded six kinds of mixed-valent TCNQ salts exhibiting semiconducting behaviors. Structural analyses revealed that the protonated 4,4′-biimidazolium derivatives formed multidirectional and multidimensional hydrogen bonds with TCNQ, and constructed two kinds of self-assembled architectures: onedimensional chainlike motifs involving TCNQ molecules and two-dimensional sheet structures composed of the alternation of segregated columns of 4,4′-biimidazolium and TCNQ. Furthermore, the hydrogen-bonding patterns regulated the electronic structures in TCNQ columns by strong cation-anion interaction, causing the nonuniform charge-distribution and semiconducting behaviors.

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Section: Introductionmentioning

confidence: 88%

Hydrogen-Bond Architectures of Protonated 4,4′-Biimidazolium Derivatives and Oligo(imidazolium)s in Charge-Transfer Salts with Tetracyanoquinodimethane

Murata

Yakiyama

Yamamoto

et al. 2008

Crystal Growth & Design

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“…In this context, we have recently designed and synthesized 4,4′-biimidazole (4,4′-H 2 Bim, Scheme ), a topological isomer of 2,2′-H 2 Bim, and its derivatives. ,− 4,4′-H 2 Bim constructed various well-defined assembled structures based on the multidirectional H-bonds intrinsically different from those of 2,2′-H 2 Bim (Scheme ). We have also revealed that the H-bond directionality of 4,4′-H 2 Bim is changed by the cis / trans -conformations, and 4,4′-H 2 Bim constructed various network structures.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Architectures and Hydrogen-Bond Directionalities of 4,4′-Biimidazole Metal Complexes Depending on Coordination Geometries

Murata

Yakiyama

Nakasuji

2010

Crystal Growth & Design

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Assembled metal complexes of 4,4 0 -biimidazole (4,4 0 -H 2 Bim), a ligand exhibiting multidirectional hydrogenbonds, were investigated in Ag I , Cu II , and Ni II complexes. The most intriguing feature of this system is that the directionality of hydrogen-bonds varies depending on the cis/trans-conformations of the ligand and the coordination geometries of the metal atoms. The [Ag I 2 (4,4 0 -H 2 Bim) 3 ] complex included ligands of both cis-and trans-conformations, the latter of which linked two metal atoms to form a planar dinuclear complex. The triple N-H 3 3 3 X 3 3 3 H-N hydrogen-bonds across the counteranions (X) formed a one-dimensional hydrogen-bond chain. The [Cu II (4,4 0 -H 2 Bim) 2 ] complexes showed a square-planar coordination sphere by the chelating coordination of two 4,4 0 -H 2 Bim units having the cis-conformation. The complexes were linked by the double N-H 3 3 3 X 3 3 3 H-N hydrogen-bonds across counteranions or solvent molecules to form one-dimensional chains. The [Cu II (4,4 0 -HBim -) 2 ] including the monodeprotonated ligand had a square-planar coordination geometry similar to those of [Cu II (4,4 0 -H 2 Bim) 2 ] complexes. The deprotonated nitrogen atom acted as a proton acceptor having a tetrahedral geometry. This complex formed a three-dimensional network by the π-stacks and N-H 3 3 3 O-H 3 3 3 N hydrogen-bonds across crystalline water molecules. The [Ni II (4,4 0 -H 2 Bim) 3 ] complexes had an octahedral coordination sphere including three chelating 4,4 0 -H 2 Bim ligands of the cis-conformation. The N-H 3 3 3 X 3 3 3 H-N hydrogen-bonds across counteranions established two-or threedimensional networks.

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“…The syntheses of some 3d metal complexes with either neutral or deprotonated 2,2 H -biimidazole were reported for the ®rst time by Holmes et al (1961). Since then, the coordination chemistry and biochemical properties of 2,2 H -biimidazole have been investigated by several workers (Uso Â n & Gimeno, 1981;Liu & Su, 1996;Tadokoro & Nakasuji, 2000;Casas et al, 2003;Zhang et al, 2003;Mano et al, 2005). This is not only because 2,2 H -biimidazole (H 2 biim) is a ligand that can coordinate to transition metals in non-deprotonated (H 2 biim), monodeprotonated (Hbiim À ) and bis-diprotonated (biim 2À ) forms, but also because it is important as a biomimetic ligand, the imidazole ring of histidine having been frequently found in a variety of proteins and metalloenzymes (Cancela et al, 2001;Sang et al, 2002).…”

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confidence: 99%

Aqua(2,2′-bi-1H-imidazole)chlorocopper(II) chloro(iminodiacetato)copper(II) monohydrate

Gao

Wei

et al. 2004

Acta Crystallogr C Cryst Struct Commun

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In the title compound, [CuCl(C6H6)N4)(H2O)][Cu(C4H5NO4)Cl].H2O, the Cu(II) atom in the cation is coordinated by one Cl- ion, two N atoms of the 2,2'-biimidazole ligand and one aqua ligand. Within the anion, the Cu(II) atom is bonded to one Cl- ion, and one N and two O atoms of the iminodiacetate ligand. Neighbouring cations and anions are connected to each other by Cu...Cl semi-coordination bonds of 2.830 (12) and 3.071 (12) A, forming a Cu2Cl2 rectangular unit. The dinuclear units further link into a polymeric chain along the a axis through Cu...O(aqua) interactions of 2.725 (3) A. Including the long coordination bonds, the geometries around the Cu atoms in the cation and anion are square-pyramidal and distorted octahedral, respectively.

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Structure and isomerization in 4,4′-biimidazoles: a comparison of crystal structures and theoretical calculations of 2,2′-dimethyl-4,4′-biimidazole and 2,2′-dimethyl-4,4′-biimidazolium bis-trifluoroactate

Cited by 10 publications

References 19 publications

Hydrogen-Bond Architectures of Protonated 4,4′-Biimidazolium Derivatives and Oligo(imidazolium)s in Charge-Transfer Salts with Tetracyanoquinodimethane

Hydrogen-Bond Architectures of Protonated 4,4′-Biimidazolium Derivatives and Oligo(imidazolium)s in Charge-Transfer Salts with Tetracyanoquinodimethane

Supramolecular Architectures and Hydrogen-Bond Directionalities of 4,4′-Biimidazole Metal Complexes Depending on Coordination Geometries

Aqua(2,2′-bi-1H-imidazole)chlorocopper(II) chloro(iminodiacetato)copper(II) monohydrate

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