3652-96-8

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 74-88-4 methyl iodide 
• 29627-62-1 N,N’-dimethyl-N,N’-di(p-toluenesulfonyl)-o-phenylenediamine 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 

Downstream Products

• 100672-48-8 4-Chloro-N-methyl-N-(2-methylamino-phenyl)-benzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 46865-17-2 2-(4-chloro-phenyl)-1,3-dimethyl-benzoimidazolium 

Relevant academic research and scientific papers

Mechanistic study on the solution-phase n-doping of 1,3-dimethyl-2-aryl-2, 3-dihydro-1H-benzoimidazole derivatives

The discovery of air-stable n-dopants for organic semiconductor materials has been hindered by the necessity of high-energy HOMOs and the air sensitivity of compounds that satisfy this requirement. One strategy for circumventing this problem is to utilize stable precursor molecules that form the active doping complex in situ during the doping process or in a postdeposition thermal- or photo-activation step. Some of us have reported on the use of 1H-benzimidazole (DMBI) and benzimidazolium (DMBI-I) salts as solution- and vacuum-processable n-type dopant precursors, respectively. It was initially suggested that DMBI dopants function as single-electron radical donors wherein the active doping species, the imidazoline radical, is generated in a postdeposition thermal annealing step. Herein we report the results of extensive mechanistic studies on DMBI-doped fullerenes, the results of which suggest a more complicated doping mechanism is operative. Specifically, a reaction between the dopant and host that begins with either hydride or hydrogen atom transfer and which ultimately leads to the formation of host radical anions is responsible for the doping effect. The results of this research will be useful for identifying applications of current organic n-doping technology and will drive the design of next-generation n-type dopants that are air stable and capable of doping low-electron-affinity host materials in organic devices.

Reactivities of acridine compounds in hydride transfer reactions

Reactivities of acridine derivatives (10-benzylacridinium ion, 1a +, 10-methylacridinium ion, 1b+, and 10-methyl-9- phenylacridinium ion, 1c+) have been compared quantitatively for hydride transfer reactions with 1,3-dimethyl-2-substituted phenylbenzimidazoline compounds, 2Ha-h. Reactions were monitored spectrophotometrically in a solvent consisting of four parts of 2-propanol to one part of water by volume at 25 ± 0.1°C. Reduction potentials have been estimated for acridine derivatives by assuming that the equilibrium constants for the reductions of 1a+-c+ by 2Hb would be the same in aqueous solution and accepting -361 mV as the reduction potential of the 1-benzyl-3- carbamoylpyridinium ion. The resulting reduction potentials, E redo, are -47 mV for 1a+, -79 mV for 1b +, and -86 mV for 1c+. Each of acridine derivatives gives a linear Bronsted plot for hydride transfer reactions. The experimental slopes were compared with those obtained by Marcus theory. This comparison shows that the kinetic data are consistent with a one-step mechanism involving no high-energy intermediates. Copyright

Marcus theory of a parallel effect on α for hydride transfer reaction between NAD+ analogues

Rate and equilibrium constants for hydride transfer from a series of 1,3-dimethyl-2-substituted phenylbenzimidazolines to a pyridinium ion, a quinolinium ion, and a phenanthridinium ion have been evaluated. Each oxidizing agent gives a linear Bronsted plot with slope, α. The α values vary systematically with the spontaniety of the reactions. They are in reasonable agreement with the predictions of modified Marcus theory. Their trend is very accurately predicted, showing a parallel (Leffler-Hammond) effect. These results make a multistep mechanism, involving high energy intermediates, very unlikely.

The reaction of 1,3-disubstituted benzimidazolium salts with Grignard reagents and a novel synthetic method for aldehydes

Aliphatic and aromatic Grignard reagents have been found to add to the double bond of 1,3-disubstituted benzimidazolium salts.The resulting substituted benzimidazolines were hydrolyzed and the aldehydes converted directly to their 2,4-dinitrophenylhydrazone derivatives.The scope and limitation of this synthesis are discussed.

Synthesis and Autoxidation of 1,3-Dialkyl-2-arylbenzimidazolines

During the attempted studies of the elimination reactions of 1,3-dimethyl-(I, R = CH3)- and 1,3-diethyl-(I, R = C2H5)-2-arylbenzimidazolines, a novel rearrangement has been observed to take place resulting in substituted amides by autoxidative ring-opening.