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Relevant academic research and scientific papers

Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides

Four benzimidazolium hydroxide compounds, in which the C2-position is attached to a phenyl group possessing hydrogen, bromine, methyl groups, or phenyl groups at the ortho positions, are prepared and investigated for stability in a quantitative alkaline stability test. The differences between the stability of the various protecting groups in caustic solutions are rationalized on the basis of their crystal structures and DFT calculations. The highest stability was observed for the m-terphenyl-protected benzimidazolium, showing a half-life in 3 m NaOD/CD3OD/D2O at 80 °C of 3240 h. A high-molecular-weight polymer analogue of this model compound is prepared that exhibits excellent mechanical properties, high ionic conductivity and ion-exchange capacity, as well as remarkable hydroxide stability in alkaline solutions: only 5 % degradation after 168 h in 2 m KOH at 80 °C. This is the most stable hydroxide-conducting benzimidazolium polymer to date.

Anion-conductive membranes based on 2-mesityl-benzimidazolium functionalised poly(2,6-dimethyl-1,4-phenylene oxide) and their use in alkaline water electrolysis

For development of anion exchange membrane (AEM) water electrolysis systems, a series of polymers was synthesised by reacting 2-mesityl-benzimidazole (BIM) and brominated poly-(2,6-dimethyl-1,4-phenylene oxide) (Br-PPO) in a Menshutkin reaction, and perme

Methyl group: A potential building block for edge-to-face interlocking of benzimidazole scaffolds in developing blue light emitting molecular aggregates

Biologically active benzimidazoles are well-known for their therapeutic applications; however, the molecular systems enable their impact in various optical applications. We report a catalyst-free synthesis of methyl-substituted benzimidazole compounds. The benzimidazole derivatives, 2-(p-tolyl)-1H-benzo[d]imidazole (4-Me) and 2-mesityl-1H-benzo[d]imidazole (246-Trime) were synthesized in an oxygenated-aqueous medium through the reaction of ortho-phenylenediamine and methyl-substituted benzaldehydes at 75 °C. The photophysical properties of the benzimidazole scaffolds were investigated in the aqueous medium. 4-Me and 246-Trime derivatives in their aggregated form in solid state displayed a red shift of absorbance and fluorescence intensity relative to their molecular form in the aqueous medium. Spectroscopic, structural and morphological characteristics of the benzimidazole compounds reveal that effective supramolecular interactions are operative to decelerate the intramolecular movements of 4-Me and 246-Trime leading to J-type molecular aggregates. The supramolecular interactions and energy framework analysis of the compounds suggest that strong and short C–H···π interactions with very strong and short intermolecular N···H hydrogen bonding play important role for the development of molecular aggregates and attribute the contribution of dispersive energy to a large extent for the stabilization of 4-Me and 246-Trime molecular aggregates. The para positional effect of the methyl group in the benzimidazole derivatives marks a notable impact on the additional stability of the blue light-emitting molecular aggregates of nano-dimension.

POLYCYCLIC COMPOUND AND AN ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE POLYCYCLIC COMPOUND OR THE COMPOSITION

Specific polycyclic compounds, a material for an organic electroluminescence device comprising said specific polycyclic compound, an organic electroluminescence device comprising said specific polycyclic compound, an electronic equipment comprising said organic electroluminescence device, a process for preparing said polycyclic compounds, and the use of said polycyclic compounds in an organic electroluminescence. (Formula I) (I)

Aerobic {Mo72V30} nanocluster-catalysed heterogeneous one-pot tandem synthesis of benzimidazoles

A novel heterogeneous one-pot protocol is developed for tandem aerobic synthesis of benzimidazoles through dehydrogenative coupling of primary benzylic alcohols and aromatic diamines co-catalysed by Keplerate-type {Mo72V30} polyoxometalate and N-hydroxyphthalimide (NHPI). The catalytic system also works well for the synthesis of benzimidazoles using benzaldehydes, as commonly used starting materials, in the absence of NHPI. The high activity of the solid nanocluster provides standard conditions avoiding current limitations of oxidation methods including high catalyst loadings. The spectral results and leaching experiments revealed that the nanocapsule preserved its structural integrity after being reused in consecutive runs.

A Tandem Aerobic Photocatalytic Synthesis of Benzimidazoles by Cobalt Ascorbic Acid Complex Coated on TiO2 Nanoparticles Under Visible Light

Abstract: In this study, we developed methods for the one pot environmentally benign synthesis of benzimidazoles by cobalt ascorbic acid complex coated on TiO2 nanoparticles via aerobic photooxidative cyclization reactions. Easy work-up procedure, reusability of the catalyst and scalable to the multi-mole scale, which is valuable for an industrial process make these catalytic systems highly attractive. Also, the combination of photocatalytic and catalytic reactions presented here may help to develop a new strategy towards the development of photocatalysis-based organic synthesis. Graphical Abstract: [Figure not available: see fulltext.].

Mild, one-pot preparation of 2-substituted benzimidazoles from organic halides

Alkyl halides are feasibly transformed into benzimidazoles by a domino reaction under solvent-free conditions. The organic halides react with o-phenylenediamines in stoichiometric amounts in the presence of pyridine-N-oxide to produce the desired substituted benzimidazoles. This domino synthesis does not require catalysts. The synthesis occurs in dry medium and the environmental impact is minimal. The method provides products without intermediate separation. A mechanism of benzimidazole synthesis is also proposed.

POLY(PHENYLENE) AND M-TERPHENYL AS PROTECTING GROUPS FOR BENZIMIDAZOLIUM HYDROXIDES

The present disclosure provides alkaline-stable m-terphenyl benzimidazolium hydroxide compounds, in which the C2-position is attached to a phenyl group having various substituents at the ortho positions. Polymers incorporating m-terphenylene repeating groups derived from these alkaline-stable benzimidazolium hydroxide compounds are also presented, along with their inclusion in ionic membranes and in electrochemical devices.

IBX works efficiently under solvent free conditions in ball milling

IBX (2-iodoxybenzoic acid), discovered in 1893, is an oxidant in synthetic chemistry whose extensive use is impeded by its explosiveness at high temperature and poor solubility in common organic solvents except DMSO. Since the discovery of Dess-Martin Periodinane in 1983, several modified IBX systems have been reported. However, under ball milling conditions, IBX works efficiently with various organic functionalities at ambient temperature under solvent free conditions. Also, the waste IBA (2-iodosobenzoic acid) produced from the reactions was in situ oxidized to IBX in the following step using oxone and thus reused for multiple cycles by conserving its efficiency (only ～6% loss after 15 cycles). This work describes an overview of a highly economical synthetic methodology which overcomes the problems of using IBX, efficiently in gram scale and in a non-explosive way. This journal is the Partner Organisations 2014.

The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation

Benzimidazoles and quinoxalines are important N-heteroaromatics with many applications in pharmaceutical and chemical industry. Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols (benzimidazoles) or diols (quinoxalines) is reported. The reactions proceed through acceptorless dehydrogenative condensation steps. Water and two equivalents of hydrogen are liberated in the course of the reactions. An Ir complex stabilized by the tridentate P^N^P ligand N2,N 6-bis(di-isopropylphosphino)pyridine-2,6-diamine revealed the highest catalytic activity for both reactions. Aromatic diamines were reacted with alcohols and diols to form benzimidazoles or quinoxalines, respectively (see scheme). In the course of the reactions, water and two equivalents of hydrogen gas were eliminated/liberated. An Ir complex stabilized by a tridentate PNP ligand was found to be an efficient catalyst in these reactions.