161664-51-3

Upstream product

• 121-43-7 Trimethyl borate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 412044-48-5 (4-cyanophenyl)magnesium bromide 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 126747-14-6 4-cyanophenylboronic acid 
• 850623-36-8 potassium (4-cyanophenyl)trifluoroborate 
• 50670-55-8 4-(4-cyanophenyl)-benzaldehyde 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 
• 460748-08-7 4'-hydroxy-3'-methyl-[1,1'-biphenyl]-4-carbonitrile 
• 57125-50-5 4'-(dodecyloxy)-[1,1'-biphenyl]-4-carbonitrile 
• 171364-82-2 4-cyanophenylboronic acid pinacol ester 

Relevant academic research and scientific papers

Borylation using group IV metallocene under mild conditions

A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway.

Enthalpy-entropy compensation combined with cohesive free-energy densities for tuning the melting temperatures of cyanobiphenyl derivatives

This work illustrates how minor structural perturbations produced by methylation of 4′-(dodecyloxy)-4-cyanobiphenyl leads to enthalpy-entropy compensation for their melting processes, a trend which can be analyzed within the frame of a simple intermolecular cohesive model. The transformation of the melting thermodynamic parameters collected at variable temperatures into cohesive free-energy densities expressed at a common reference temperature results in a novel linear correlation, from which melting temperatures can be simply predicted from molecular volumes. In tune with temperature! The transformation of the melting thermodynamic parameters into cohesive free-energy densities (CFED) for 4′-(n-oxy)-i′-methyl-j-methyl-4-cyanobiphenyl (CnLi′,j) provides a novel linear correlation for predicting melting temperatures in a simple way. Copyright

Full-colour luminescent compounds based on anthracene and 2,2′-dipyridylamine

Starting from two simple units of anthracene and 2,2′-dipyridylamine, a series of new luminescent compounds 1-8 were designed and synthesized by a combined strategy of changing the connection mode between the two units, extending the conjugation size, and introducing an additional electron donor. Photophysical properties of 1-8 were investigated and discussed on the basis of solvatochromic behaviour, theoretical calculations, crystal structure, and optimized structures. Interestingly, the emission wavelengths of these compounds could be successfully tuned from violet to red both in solutions and the solid-state, and prominent positive solvatochromism was observed for the compounds with a D-π-A framework. Consider compound 7 as an example, it shows peaks at 526 nm and 627 nm in cyclohexane and DMSO, respectively. Meanwhile, the quantum yield was decreased from 0.80 in cyclohexane to 0.12 in DMSO. The introduction of bulky groups was demonstrated to be effective for suppressing the aggregation effect and thus improving the solid state emission quantum yield. These results indicate that the combined structure modulation strategy offers a powerful tool for tuning the emission behaviour. To demonstrate the possibility of practical applications, 2 was employed as the emitting material for the fabrication of deep-blue organic light-emitting diodes (OLEDs), which showed a maximum external quantum efficiency of 2.2%. The CIE coordinates of (0.15, 0.08) are indicative of excellent blue color purity.

Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base

We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding biaryl compounds in one flow.

Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4- ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids

A simple protocol for the Pd(OAc)2-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110°C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-onesand aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a largevariety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz,-OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenrichedα-aryl-substituted β-amino acids. We present a general approach for the synthesis of (2S)-isopropyl-5-aryl-2,3- dihydro-4(H)-pyrimidin-4-ones by Suzuki-Miyaura reaction of aryltrifluoroborate salts with(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones in the presence of a palladium catalyst and a base. The arylated compounds were transformed into enantioenriched α-aryl-substituted β-amino acids. Copyright

Effects of substitution and terminal groups for liquid-crystallinity enhanced luminescence of disubstituted polyacetylenes carrying chromophoric terphenyl pendants

Liquid-crystalline and light-emitting poly(2-alkyne)s containing terphenyl cores with hexamethyleneoxy spacers, and cyano or n-propoxy tails - [CH3C=C(CH2)6O-terphenyl-R] n -, where R=CN, CH3PA6CN, R=OCH2CH 2CH3, CH3PA6OPr, were synthesized. The effects of the substitution and terminal groups on the properties, especially the mesomorphic and optical properties of the polymers, were investigated. The disubstituted acetylene monomers (CH3A6CN, CH3A6OPr) were prepared through multistep reaction routes and were polymerized by WCl6-Ph4Sn in good yields (up to 82%). All the monomers and CH3PA6CN exhibited the enantiotropic SmA phase with a monolayer arrangement at elevated temperatures, whereas CH3PA6OPr formed a bilayer SmAd packing arrangement. Upon excitation at 330 nm, strong UV and blue emission peaks at 362 and 411 nm were observed in CH3PA6OPr and CH3PA6CN, respectively. The luminescent properties of CH3PA6CN and CH3PA6OPr have been improved by introducing the methyl substituted group, and the quantum yield of the polymer with cyano tail CH3PA6CN (Φ = 74%) was found to be higher than that of CH3PA6OPr (Φ = 60%). Compared to polyacetylene parents, both CH3PA6OPr and CH3PA6CN showed a narrower energy gap. This demonstrated that the electrical conductivities of polyacetylenes could be enhanced by attaching appropriate pendants to the conjugated polyene backbones.

Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen

Novel disubstituted propiolates bearing chromophoric terphenylene mesogenic groups, namely, 40-cyano- 4-terphenylyl-2-octynate M(CN) and 40-methoxyl-4-terphenylyl- 2-octynate M(OCH3) are synthesized, where the terphenyl groups are connected to the C≡C through ester linkage directly. Using transition-metal catalysts such as the classical MoCl 5- and WCl6-based metathesis catalysts, the polymerization of the M(CN) and M(OCH3) are carried out in a series of different solution, however, did not obtain any products. It suggests that the WCl 6- and MoCl5-based catalysts are poisoned by the polar groups, on the other hand, the bulk terphenyl groups and the long alkyl chain around the C≡C bond might inhibit the reaction. M(CN) displays monotropic nematicity, whereas M(OCH3) exhibits enantiotropic nematicity and smecticity (SmAd) with a bilayer arrangement when cooled and heated. Ultraviolet spectroscopy and photoluminescence measurements also show that the terphenyl groups endow disubstituted propiolates with strong UV light absorption and high photoluminescence. Akademiai Kiado, Budapest, Hungary 2009.