3652-98-0

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 186354-20-1 C₆H₄BrMgNO₂ 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 29627-62-1 N,N’-dimethyl-N,N’-di(p-toluenesulfonyl)-o-phenylenediamine 

Downstream Products

• 100672-50-2 4-nitro-benzoic acid-(N-methyl-2-methylamino-anilide) 
• 555-16-8 4-nitrobenzaldehdye 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 47045-83-0 1,3-dimethyl-2-(4-nitro-phenyl)-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.

Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines

A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.

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.