39778-14-8

Usage

Chemical class

Benzimidazolium salts

Common use

Organic synthesis and development of new materials

Preparation method

Reaction of 1-methyl-3-phenylbenzimidazolium chloride with sodium iodide

Role

Effective catalyst for various reactions

Applications

Synthesis of other benzimidazolium salts, functionalization of carbon-carbon double bonds

Potential uses

Pharmaceutical industry, intermediate in organic chemical reactions

Importance

Versatile compound in the field of organic chemistry

Upstream product

• 2622-60-8 1-phenyl-1H-benzoimidazole 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 
• 51-17-2 benzoimidazole 
• 591-50-4 iodobenzene 
• 534-85-0 N-phenyl-1,2-benzenediamine 

Downstream Products

• 1309866-49-6 bis(N-methyl-N'-phenylbenzimidazol-2-ylidene)diiodonickel(II) 

Relevant academic research and scientific papers

Efficient NIR electrochemiluminescent dyes based on ruthenium(ii) complexes containing an N-heterocyclic carbene ligand

Three new ruthenium(ii) complexes containing an N-heterocyclic carbene (NHC) ligand (RuNHC) have been successfully synthesized and proved to be efficient near-infrared (NIR) ECL (electrogenerated chemiluminescence) luminophores. In addition to the advanta

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.

Neutral Cyclometalated Iridium(III) Complexes Bearing Substituted N-Heterocyclic Carbene (NHC) Ligands for High-Performance Yellow OLED Application

The synthesis, crystal structure, and photophysics of a series of neutral cyclometalated iridium(III) complexes bearing substituted N-heterocyclic carbene (NHC) ancillary ligands ((CN)2Ir(R-NHC), where CN and NHC refer to the cyclometalating ligand benzo[h]quinoline and 1-phenylbenzimidazole, respectively) are reported. The NHC ligands were substituted with electron-withdrawing or -donating groups on C4′ of the phenyl ring (R = NO2 (Ir1), CN (Ir2), H (Ir3), OCH3 (Ir4), N(CH3)2 (Ir5)) or C5 of the benzimidazole ring (R = NO2 (Ir6), N(CH3)2 (Ir7)). The configuration of Ir1 was confirmed by a single-crystal X-ray diffraction analysis. The ground- and excited-state properties of Ir1-Ir7 were investigated by both spectroscopic methods and time-dependent density functional theory (TDDFT) calculations. All complexes possessed moderately strong structureless absorption bands at ca. 440 nm that originated from the CN ligand based 1π,π*/1CT (charge transfer)/1d,d transitions and very weak spin-forbidden 3MLCT (metal-to-ligand charge transfer)/3LLCT (ligand-to-ligand charge transfer) transitions beyond 500 nm. Electron-withdrawing substituents caused a slight blue shift of the 1π,π*/1CT/1d,d band, while electron-donating substituents induced a red shift of this band in comparison to the unsubstituted complex Ir3. Except for the weakly emissive nitro-substituted complexes Ir1 and Ir6 that had much shorter lifetimes (≤160 ns), the other complexes are highly emissive in organic solutions with microsecond lifetimes at ca. 540-550 nm at room temperature, with the emitting states being predominantly assigned to 3π,π*/3MLCT states. Although the effect of the substituents on the emission energy was insignificant, the effects on the emission quantum yields and lifetimes were drastic. All complexes also exhibited broad triplet excited-state absorption at 460-700 nm with similar spectral features, indicating the similar parentage of the lowest triplet excited states. The highly emissive Ir2 was used as a dopant for organic light-emitting diode (OLED) fabrication. The device displayed a yellow emission with a maximum current efficiency (ηc) of 71.29 cd A-1, a maximum luminance (Lmax) of 32747 cd m-2, and a maximum external quantum efficiency (EQE) of 20.6%. These results suggest the potential of utilizing this type of neutral Ir(III) complex as an efficient yellow phosphorescent emitter.

Twist it! the acid-dependent isomerization of homoleptic carbenic iridium(III) complexes

The first successful meridional to facial isomerization of homoleptic carbenic iridium(iii) complexes is presented. The Br?nsted-acid-mediated procedure allows the conversion of large amounts of material and additionally provides an in situ purification b

Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device

An organometallic complex that has high emission efficiency and high heat resistance and emits blue light is provided as a novel substance. In a light-emitting element including a light-emitting layer between a pair of electrodes, the light-emitting layer

Osmium(II)-bis(dihydrogen) complexes containing C aryl, C NHC-chelate ligands: Preparation, bonding situation, and acidity

The hexahydride complex OsH6(PiPr3)2 (1) reacts with the BF4-salts of 1-phenyl-3-methyl-1-H-benzimidazolium, 1-phenyl-3-methyl-1-H-5,6-dimethyl-benzimidazolium, and 1-phenyl-3-methyl-1-H-imidazolium t

N -heterocyclic carbenes: Versatile second cyclometalated ligands for neutral iridium(III) heteroleptic complexes

With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)s

Enlarging the π system of phosphorescent (C^C*) cyclometalated platinum(II) NHC complexes

Cyclometalated (C^C*) platinum(II) N-heterocyclic carbene (NHC) complexes are emerging as a new class of phosphorescent emitters for the application in organic light-emitting devices (OLEDs). We present the synthesis of six new complexes of this class to

Exploring a unique reactivity of N-heterocyclic carbenes (NHC) in rhodium(III)-catalyzed intermolecular C-H activation/annulation

Disclosed herein is the unique conjugative role of N-heterocyclic carbene (NHC) ligands as a directing group in aromatic C-H activation, coupled with a facile NHC-alkenyl annulative reductive elimination which guided the RhIII-catalyzed intermo