492-98-8

Usage

Uses

Used in the Preparation of Photoluminescent Complexes:
2,2'-BIIMIDAZOLE is used as a key component in the preparation of complexes that exhibit photoluminescence and optical properties. Its unique structure allows for the formation of complexes with specific characteristics, making it a valuable compound in the development of materials for optoelectronic applications.
Used in the Semiconductor Industry:
In the semiconductor industry, 2,2'-BIIMIDAZOLE is used in the preparation of bismuth biimidazoles, which are considered as potential semi-conductors. These materials can be utilized in the development of electronic devices and components, taking advantage of their semi-conducting properties.
Overall, 2,2'-BIIMIDAZOLE is a versatile compound with applications in various industries, including optoelectronics and semiconductors, due to its unique chemical structure and properties.

Upstream product

• 599-01-9 3,3,3-trichloro-2-hydroxy-propionic acid 
• 131543-46-9 Glyoxal 
• 631-61-8 ammonium acetate 
• 496-45-7 glyoxal sulfate 
• 3039-13-2 dibromoacetaldehyde 
• 93241-62-4 1,2-dihydroxyethylenediamine dihydrochloride 
• 106536-97-4 Bis-N-(2,2-dimethoxyethylacetamidine) dihydrochloride 
• 107-21-1 ethylene glycol 

Downstream Products

• 37570-85-7 1-Methyl-2,2'-biimidazol 
• 471-46-5 Oxalamide 
• 37570-94-8 1,1'-dimethyl-2,2'-biimidazole 
• 37572-50-2 1,1'-diethyl-2,2'-biimidazolyl 
• 75-05-8 acetonitrile 
• 114074-88-3 {Cu(2,2'-biimidazole)(triphenylphosphine)2}BF₄ 
• 132530-30-4 {RuH(CO)(C₃H₃N₂C₃H₃N₂)(P(C₆H₅)3)2}⁽¹⁺⁾*ClO₄^(1-)={RuH(CO)(C₃H₃N₂C₃H₃N₂)(P(C₆H₅)3)2}ClO₄ 
• 107478-99-9 [Mn(CO)2(P(OC₆H₅)3)2((C₃N₂H₃)(C₃N₂H₂))] 
• 89823-99-4 [(η5-C5H5)Ru(2,2'-biimidazole)(PPh3)]ClO4 
• 308144-56-1 [ReOCl₂(OPPh₃)(biimH₂)]Cl 

Relevant academic research and scientific papers

A comprehensive study on the dye adsorption behavior of polyoxometalate-complex nano-hybrids containing classic β-octamolybdate and biimidazole units

Six new hybrids based on β-[Mo8O26]4? polyoxometalates, [Ni(H2biim)3]2[β-Mo8O26]?8DMF(1); (DMA)2[M(H2biim)2(H2O)2][β-Mo8O26]?4DMF (M = Ni (2), Co (3)), DMA = dimethyl-ammonium, H2biim=2,20-biimidazole); [M(H2biim)(DMF)3]2[β-Mo8O26]?2DMF (M = Zn (4), Cu (5)); [(DMA)2 [Cu(DMF)4][β-Mo8O26]?2DMF]n (6), have been successfully synthesized and characterized. Compounds 2–5 show favorable capacity to adsorb methylene blue (MB) at room temperature, and they can selectively capture MB molecules from binary-mixture solutions of MB/MO (MO = Methyl Orange), or MB/RhB (RhB = Rhodamine B). Compound 3 can uptake up to 521.7 mg g?1 MB cationic dyes rapidly, which perform the maximum adsorption in an hour among the reported materials as far as we know. The compounds are stable and still work very efficiently after three cycles. For compound 3, the preliminary adsorption mechanism studies indicated that the adsorption is an ion exchange process and the adsorption behavior of polyoxometalate-complex can be benefited from additional exchangeable protons in the complex cations.

Multiplex Proton-Transfer and Electron-Transfer Natures Based on the 2,2'-Bi-1H-imidazole System. I. Acid Dissociation Constants and Redox Properties in Solution

The 2,2'-bi-1H-imidazole (H2BIM) derivatives were studied from the point of the interplay of proton-transfer (PT) and electron (charge)-transfer (CT) interactions.Seven new states among the speculated 25 independent species were identified based on the study of their redox and acid dissociation properties.Isoelectronic substitution of four sulfur atoms of the dication state of tetrathiafulvalene (TTF2+) by four imino groups was found to increase the stability of the dication state 2,2'-bi-1H-imidazolium (H4BIM2+) with aromatic 6?-6? character.The high PT character of H3BIM+ (2-(2-1H-imidazolyl)-1H-imidazolium) and H4BIM2+ compared with that of corresponding hydroquinone system was clearly observed.The onsite Coulomb repulsion energy for electron-transfer (U1CT) was evaluated for various ?-electron acceptor and donor systems.It was found that the U1CT values decrease linearly with increasing the length of a molecule, which can divide the molecular systems into two-classifications, i.e. electron and dications.The onsite Coulomb repulsion energy for two-step proton-transfer processess (U1PT) was newly defined and evaluated for the H2BIM, H4BIM2+, hydroquinone (H2Q), and bis(4-hydroxyphenyl) disulfide (HPDS) systems.The U1PT values become constant above a certain molecular length (rc).Below rc the U1PT values increase linearly with decreasing the distance r regardless of Wuerster and Weitz structures, approximately.The H2BIM (H4BIM2+) system has large U1PT values in comparison with H2Q and HPDS systems.

Bridged Derivatives of 2,2'-Biimidazole

The reaction of 2,2'-biimidazole with 1,n-dihaloalkanes or o-xylylene dibromide leads to a series of N,N'-bridged derivatives.When these substances are treated with a second equivalent of 1,n-dihaloalkane, a series of bis-annelated biimidazolium salts is obtained.The conformations of these species are discussed with regard to their electronic absorption spectra and their 300-MHz 1H NMR spectra.The barriers for conformational inversion are found to be lower than for the corresponding bis-annelated 2,2'-bipyridinium salts.The redox properties of these salts are measured in CH3CN and DMSO, and their reductions are found to become increasingly more difficult and less reversible as the system becomes less planar.These results are explained primarily based on the greater N,N'-distance in 2,2'-biimidazole as compared with 2,2'-bipyridine.

Studies of ruthenium(ii)-2,2′-bisimidazole complexes on binding to G-quadruplex DNA and inducing apoptosis in HeLa cells

Three ruthenium(ii) complexes [Ru(bpy)2(biim)]2+ (1), [Ru(phen)2(biim)]2+ (2) and [Ru(p-mopip) 2-(biim)]2+ (3) (where bpy is 2,2′-bipyridine, phen is 1,10-phenanthroline, biim is 2,2′-bisimidazole and p-mopip is 2-(4-methoxyphenyl)-imidazo-[4,5f]phenanthroline), have been synthesized and characterized. The interactions of human telomeric DNA oligomers 5′-G 3(T2AG3)3-3′ (HTG21) with ruthenium(ii) complexes were investigated via UV-vis, fluorescence resonance energy transfer (FRET) melting assay, polymerase chain reaction (PCR) stop assay, and circular dichroism (CD) measurements. The results indicated that the three ruthenium(ii) complexes could stabilize the formation of human telomeric G-quadruplex DNA, and complex 2 was found to be the most efficient. In vitro cytotoxicity assay by MTT also showed that complex 2 was superior to complexes 1 and 3 in inhibiting the growth of cancer cells. Telomeric repeat amplification protocol (TRAP) showed that complexes 2 and 3 led to an inhibition of the telomerase activity, and complex 2 was the significantly better inhibitor. Flow cytometric analysis and evaluation of mitochondrial membrane potential demonstrated that complex 2 inhibited the growth of HeLa cells through induction of apoptotic cell death, as evidenced by the depletion of mitochondrial membrane potential in HeLa cells.

Tetracarboxyl-functionalized ionic liquid: Synthesis and catalytic properties

Novel tetracarboxyl-functionalized 2,2′-biimidazolium-based ionic liquids (ILs) with different anions were synthesized in two steps from readily available and sustainable starting materials including ammonium acetate, glyoxal, and halogenated propionic acid. The functionalized IL exhibited higher catalytic activity towards the cycloaddition of CO2 to terminal epoxides. With propylene oxide as a substrate, the optimum yield of propylene carbonate reached 82.7% at an initial CO2 pressure of 2.0MPa for 4h at 140°C. Moreover, the functionalized IL catalyst displayed a high stability and can be reused for at least five cycles without obvious loss of catalytic activity. The results provide a simple and economical way to synthesize multi-functionalized imidazolium-based ILs with versatile potential applications.

Synthesis and Properties of 4,4',5,5'-Tetranitro-1H,1'H-2,2'-Biimidazole Salts: Semicarbazidium, 3-Amino-1,2,4-Triazolium, and 5-Aminotetrazolium Derivatives

[Figure not available: see fulltext.] Ionic derivatives of 4,4',5,5'-tetranitro-1H,1'H-2,2'-biimidazole have recently been identified as interesting low-sensitivity explosive compounds that combine low vulnerability to mechanical stimuli with high performance. In this work, the synthesis of bis-semicarbazidium), bis(3-amino-1H-1,2,4-triazol-4-ium), and bis(5-amino-4H-tetrazol-1-ium) 4,4',5,5'-tetranitro-2,2'-biimidazol-1-ides is described, and some of their experimental and calculated explosive properties are presented. 4,4',5,5'-Tetranitro-1H,1'H-2,2'-biimidazole was synthesized by nitration of 2,2'-biimidazole with nitric acid in polyphosphoric acid and produced the salts in good yields and purity by reaction with semicarbazide hydrochloride in water, 3-amino-1,2,4-triazole in methanol, and 5-aminotetrazole in diethyl ether. The obtained salts were characterized by NMR and infrared spectroscopy, elemental analysis, thermal analysis, and small-scale safety testing impact and friction sensitivity). The measured densities and standard enthalpy of formation, as well as calculated performance characteristics are reported. The compounds are thermally stable up to 180–210°C and insensitive to mechanical stimuli and have slightly better performance than trinitrotoluene with regard to calculated detonation parameters.

Fully C/N-Polynitro-Functionalized 2,2'-Biimidazole Derivatives as Nitrogen- and Oxygen-Rich Energetic Salts

Through the use of a fully C/N-functionalized imidazole-based anion, it was possible to prepare nitrogen- and oxygen-rich energetic salts. When N,N-dinitramino imidazole was paired with nitrogen-rich bases, versatile ionic derivatives were prepared and fully characterized by IR, and 1H, and 13C NMR spectroscopy and elemental analysis. Both experimental and theoretical evaluations show promising properties for these energetic compounds, such as high density, positive heats of formation, good oxygen balance, and acceptable stabilities. The energetic salts exhibit promising energetic performance comparable to the benchmark explosive RDX (1,3,5-trinitrotriazacyclohexane). The combination of a fully C/N-functionalized biimidazole-based anion with nitrogen-rich cations gives rise to a series of nitrogen- and oxygen-rich energetic salts. Some of them show excellent detonation properties with acceptable thermal stabilities and sensitivities, which are comparable to the benchmark explosive RDX (1,3,5-trinitrotriazacyclohexane).

An ionic liquid-coordinated palladium complex: A highly efficient and recyclable catalyst for the Heck reaction

The monoquaternary product of 2,2′-biimidazole with iodobutane is an ionic liquid that acts as both the solvent and ligand for catalytic reactions. A new palladium complex was prepared by adding PdCl2 to this ionic liquid to form a catalytic solution that is effective for Heck reactions with good recyclability.

Energetic derivatives of 4, 4',5, 5'-Tetranitro-2, 2'-bisimidazole (TNBI)

4, 4',5, 5'-Tetranitro-2, 2'-bisimidazole (TNBI) was synthesized by nitration of bisimidazole (BI) and recrystallized from acetone to form a crystalline acetone adduct. Its ammonium salt (1) was obtained by the reaction with gaseous ammonia. In order to explore new explosives or propellants several energetic nitrogen-rich 2:1 salts such as the hydroxylammonium (3), guanidinium (4), aminoguanidinium (5), diaminoguanidinium (6) and triaminoguanidinium 7 4, 4',5, 5'-tetranitro-2, 2'-bisimidazolate were prepared by facile metathesis reactions. In addition, methylated 1, 1'-dimethyl-4, 4',5, 5'-tetranitro-2, 2'-bisimidazole (Me2TNBI, 8) was synthesized by the reaction of 2 and dimethyl sulfate. Metal salts of TNBI can also be easily synthesized by using the corresponding metal bases. This was proven by the synthesis of pyrotechnically relevant dipotassium 4, 4',5, 5'-tetranitro-2, 2'-bisimidazolate (2), which is a brilliant burning component e.g. in near-infrared flares. All compounds were characterized by single crystal X-ray diffraction, NMR and vibrational spectroscopy, elemental analysis and DSC. The sensitivities were determined by BAM methods (drophammer and friction tester). The heats of formation were calculated using CBS-4M electronic enthalpies and the atomization method. With these values and mostly the X-ray densities different detonation parameters were computed by the EXPLO5 computer code. Due to the great thermal stability and calculated energetic properties, especially guanidinium salt 4 could be served as a HNS replacement. Copyright

C6N10O4: Thermally Stable Nitrogen-Rich Inner Bis(diazonium) Zwitterions

Two nitrogen-rich inner bis(diazonium) salts, the 4,4′-dinitro-5,5′-diazo-2,2′-bisimidazole (2) and the 4,4′-dinitro-5,5′-diazo-3,3′-bispyrazole (4) zwitterions, are described. Compound 2 was synthesized unexpectedly from the nitration of 4,4′-dinitro-5,5′-diamino-1H,1′H-2,2′-bisimidazole (1) in a mixture of trifluoroacetic anhydride and 100% nitric acid. Both 2 and 4 show good thermal stability, especially 2 has a decomposition temperature of 199 °C, which is the highest one in any of the reported hydrogen-free nitrogen-rich diazonium salts.