37570-94-8

Basic information

• Product Name: 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL
• Synonyms: 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL;1-methyl-2-(1-methylimidazol-2-yl)imidazole
• CAS NO: 37570-94-8
• Molecular Formula: C₈H₁₀N₄
• Molecular Weight: 162.1918
• Mol File: 37570-94-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 366.688 °C at 760 mmHg
• Flash Point: 175.567 °C
• Appearance: /
• Density: 1.215 g/cm³
• CAS DataBase Reference: 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL(37570-94-8)
• EPA Substance Registry System: 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL(37570-94-8)

Safety Data

• Hazardous Substances Data: 37570-94-8(Hazardous Substances Data)

Usage

General Description

1,1'-dimethyl-1H,1'H-[2,2']biimidazolyl is a chemical compound with a molecular formula C12H14N4. It is a symmetric bidentate ligand commonly used in coordination chemistry and catalysis. 1,1'-DIMETHYL-1H,1'H-[2,2']BIIMIDAZOLYL contains two imidazole rings connected by a methylene bridge, and the methyl groups are attached to the nitrogen atoms of the imidazole rings. The 1,1'-dimethyl-1H,1'H-[2,2']biimidazolyl ligand has been extensively studied for its ability to form stable complexes with various metal ions, making it useful in the synthesis of metal-organic frameworks and coordination polymers. Its unique structure and versatile coordination properties make it a valuable tool in the field of inorganic chemistry and materials science.

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 694-59-7 pyridine N-oxide 
• 37067-95-1 2-iodo-1-methyl-1H-imidazole 
• 492-98-8 2,2'-biimidazole 
• 80-48-8 methyl p-toluene sulfonate 
• 88346-01-4 1,1'-dimethyl-3,3'-methylenediimidazolium diiodide 
• 74-88-4 methyl iodide 
• 273-53-0 benzoxazole 
• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 

Relevant articles and documents

Facile C-N bond cleavage promoted by cuprous oxide: Formation of C-C-coupled biimidazole from its methylene-bridged congener

The methylenebis(N-alkylimidazolium) halides are converted to dialkylbiimidazoles by cuprous oxide with concurrent C-N bond cleavage and C-C bond formation. This unusual C-N bond cleavage is proposed to involve a Cu(I)-NHC (N-heterocyclic carbene) complex. The reaction is unique, as it involves C-H bond activation, C-N bond cleavage, and C-C bond formation.

Incrementing Stokes Shifts through the Formation of 2,2′-Biimidazoldiium Salts

The formation of biimidazoldiium structures by the introduction of methyl substituents on the N atoms at the 3 and 3′ positions of 2,2′-biimidazoles led to increments in the Stokes shift of these structures. Based on time-dependent density functional theory (TDDFT) calculations, the imidazolium rings become distorted and the N atoms of the imidazolium rings underwent structural changes through sp2 to sp3 rehybridization in the excited states.

Effect of ancillary ligands on the properties of diphenylphosphoryl-substituted cationic Ir(iii) complexes

A new class of diphenylphosphoryl-substituted cationic cyclometalated Ir(iii) complexes [Ir(POFdFppy)2(N^N)]+PF6- (dFppy = 2-(2,4-difluorophenyl)pyridine) (POF1-POF6) with different N^N ancillary ligands have been synthesized and characterized. The influences of N^N ancillary ligands on the photophysical and electrochemical properties of the Ir(iii) complexes have been investigated systematically. The results demonstrate that the photoluminescence quantum yields (ΦPL) of the complexes are dependent on the N^N ancillary ligands. POF1-POF3 equipped with phenanthroline or bipyridine ancillary ligands exhibit intense emission bands at 465-497 nm and high ΦPL in the range of 56-61% in CH2Cl2. The biimidazole-type complexes POF4-POF6 exhibit an obvious substituent effect on the photophysical and electrochemical properties. Although the emission spectra of POF4 and POF5 show similar fine structures, the ΦPL of POF5 bearing two methyl groups at the biimidazole moiety is remarkably lower (5%) than that of POF4 (45%, unmodified biimidazole). POF6 bearing two phenyl groups at the biimidazole moiety exhibits a red-shift and a weak emission band, and an extremely low ΦPL (3%). However, the photoluminescence quantum yields of POF5 and POF6 (35% and 41% in EC film, 40% and 65% in neat film, respectively) in the film increase effectively in comparison to those in solution. Cyclic voltammetry shows further that the structure of the ancillary ligand affects the redox properties. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed to provide insights into the electronic structures of POF1-POF6. POF1 bearing a 1,10-phenanthroline moiety demonstrates the highest oxygen sensitivity.