34745-92-1

Upstream product

• 1552-41-6 diethyl [(4-cyanophenyl)methyl]phosphonate 
• 104-88-1 4-chlorobenzaldehyde 
• 1615-02-7 p-chlorocinnamic acid 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 1073-67-2 4-vinylbenzyl chloride 
• 3058-39-7 4-iodobenzonitrile 
• 222400-79-5 diethyl (4-cyanobenzyl)phosphonate 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 126747-14-6 4-cyanophenylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 
• 180466-98-2 (4-cyanobenzyl)phosphonic acid dimethyl ester 
• 3435-51-6 4-ethenylbenzonitrile 

Downstream Products

• 1609430-94-5 4-((1S,2S)-2-(4-chlorophenyl)-1,2-dihydroxyethyl)benzonitrile 
• 619-65-8 4-cyanobenzoic Acid 
• 74-11-3 para-chlorobenzoic acid 

Relevant academic research and scientific papers

Efficient deep blue emission by 4-styrylbenzonitrile derivatives in solid state: Synthesis, aggregation induced emission characteristics and crystal structures

Organic fluorescent molecules with π-conjugated system have shown great importance in numerous applications including bioimaging and optoelectronics. Planar aggregation-induced emissive (AIE) organic compounds with efficient solid-state luminescence are rarely developed and urgently needed in various applications. In this work, highly planar 4-styrylbenzonitrile derivatives have been synthesized. Most of these compounds show strong AIE properties with hundred-fold fluorescent enhancement. Moreover, these molecules are deep blue emissive in solid state, exhibiting good to excellent fluorescence quantum efficiency. The single crystal analysis shows that adjacent molecules could form special J-type aggregation. The intramolecular rotations are efficiently restricted by various noncovalent interactions. These molecular arrangements could be essential for the observed strong emission in aggregated and solid state. This work has paved a new path to efficient AIE-active organic emitters with highly planar conformations from 4-styrylbenzonitrile structure.

Stilbene solid fluorescent material

The invention discloses a stilbene solid fluorescent material, and belongs to the field of functional materials. The stilbene compound provided by the invention has a simple molecular skeleton structure, and the synthesis method is simple and convenient. The fluorescent material has weak fluorescence in a solution state. By testing the fluorescence emission intensity of the fluorescent material in a tetrahydrofuran and water mixed solvent with the water content of 0-99%, the fluorescent material is found to have obvious aggregation-induced emission property. The fluorescent material can emit bright blue fluorescence in a solid powder state, has very high absolute fluorescence quantum yield, and has a potential application in the photoelectric field.

Palladium-catalyzed decarboxylative coupling of α,β-unsaturated carboxylic acids with aryl tosylates

We report a general method for selective cross-coupling of α,β-unsaturated carboxylic acids with aryl tosylates enabled by versatile Pd(II) complexes. This method features the general cross-coupling of ubiquitous α,β-unsaturated carboxylic acids by decarboxylation. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Pd(II) catalysts, scalability and wide substrate scope. The reaction proceeds with high trans selectivity to furnish valuable (E)-1,2-diarylethenes.

Hydrogen Peroxide Promoted Mizoroki-Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes

Mizoroki-Heck reactions, which are well-known for aryldiazonium salts and which have recently been described for arylhydrazines, have now been extended to phenyldiazenes. In situ generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium-silver(I) system.

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6nm diameters in Pd(0) oxidation state well-dispersed with 30wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80 °C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Highly efficient and magnetically recyclable graphene-supported Pd/Fe3O4 nanoparticle catalysts for Suzuki and Heck cross-coupling reactions

Herein, we report a facile and efficient one-step method for the synthesis of highly active, Pd/Fe3O4 nanoparticles supported on graphene nanosheets (Pd/Fe3O4/G) that exhibit excellent catalytic activity for Suzuki and Heck coupling reactions and that can be magnetically separated from the reaction mixture and recycled multiple times without loss of catalytic activity. The synthesis approach is based on the Microwave (MW)-assisted reduction of palladium and ferric nitrates in the presence of graphene oxide (GO) nanosheets using hydrazine hydrate as the reducing agent. The results provide a fundamental understanding of the system variables by comparing the catalytic activity and recyclability of four different catalysts with different properties. The most active and recyclable catalyst contains 7.6 wt% Pd nanoparticles with 4-6 nm diameters in Pd(0) oxidation state well-dispersed with 30 wt% Fe3O4 nanoparticles with 12-16 nm diameters on highly reduced GO containing a C/O ratio of 8.1. These combined properties produce remarkable catalytic activity for Suzuki cross coupling reactions under MW reaction conditions with an extremely high turnover number (TON) of 9250 and turn over frequency (TOF) of 111,000 h-1 at 80°C. The magnetic properties imparted by the Fe3O4 component of the catalyst enables the catalyst to be easily isolated and recycled, thus greatly simplifying the ability to purify the reaction products and increasing the economic value of the catalyst. The utility of these magnetic catalysts towards Suzuki and Heck cross coupling reactions with a variety of functionalized substrates was also demonstrated.

Transition-metal-free and chemoselective NaOtBu-O 2-mediated oxidative cleavage reactions of vic-1,2-diols to carboxylic acids and mechanistic insight into the reaction pathways

A method for efficient oxidative cleavage of vic-1,2-diols using a NaO tBu-O2 system resulted in the formation of carboxylic acids in high yields. The present protocol is an eco-friendly alternative to a conventional transition-metal-based method. This new strategy allows large-scale production with nonchromatographic purification while also suppressing competitive reaction pathway such as benzilic acid rearrangement.

Effects of substituent and solvent on the UV absorption energy of 4,4′-disubstituted stilbenes

Twenty five samples of 4,4′-disubstituted stilbene derivatives were synthesized, and their UV absorption max wavelengths were determined in over 10 kinds of solvents including cyclohexane, ether, chloroform, acetonitrile and ethanol, in which 242 experimental data were recorded. The effects of substituents and solvents on the energy of their UV absorption max wavelengths were discussed. The research results showed: the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was mainly affected by their intramolecular structure (substituent effect) in a given solvent, that is, the energy is dominated by both of excited-state substituent parameter σ CC ex and polar substituent constant σ p. While their energy was dominated by the substituent effect and solvent effect in different kinds of solvents. An equation quantifying the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was developed. In addition, it is found that the n-octanol/water partition coefficient (logP) is more effective than the solvatochromic dye (E T(30)) in scaling the solvent effect. The equation employed the parameter logP has a better correlation and more specific physical meaning. Further, the energies of UV absorption max wavelengths of some reported compounds were predicted by the obtained equation, which are in agreement with their experimental values.

Microwave-assisted synthesis of palladium nanoparticles supported on graphene: A highly active and recyclable catalyst for carbon-carbon cross-coupling reactions

We have developed an efficient method to generate highly active Pd nanoparticles supported on graphene (Pd/G) by microwave-assisted chemical reduction of the corresponding aqueous mixture of a palladium salt and dispersed graphite oxide (GO) sheets. The Pd/G demonstrated excellent catalytic activity for the carbon-carbon cross-coupling reactions (Suzuki, and Heck) with a broad range of utility under ligand-free ambient conditions in an environmentally friendly solvent system. It also offers a remarkable turnover frequency (108,000 h-1) observed in the microwave-assisted Suzuki cross-coupling reactions with easy removal from the reaction mixture, recyclability with no loss of activity, and significantly better performance than the well-known commercial Pd/C catalyst. The catalyst was fully characterized by a variety of spectroscopic techniques including X-ray diffraction (XRD), Raman, TGA, electron microscopy (SEM, TEM), and X-ray photoelectron spectroscopy (XPS). The remarkable reactivity of the Pd/G catalyst toward Suzuki cross-coupling reactions is attributed to the high degree of the dispersion and concentration of Pd(0) nanoparticles supported on graphene sheets with small particle size of 7-9 nm due to an efficient microwave-assisted reduction method.

Preparation of donor-acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

The syntheses and crystal structures of a series of fluoro-substituted halogeno (Cl, Br, I)-cyano-stilbenes containing donor and acceptor groups (D-π-A) are reported. These molecules show a tendency to form antiparallel chain-like structures and herringbone packing, crystallising predominantly in a centric space group. However, second harmonic generation measurements bear evidence for orientational disorder leading to partial polar order below the ordinary X-ray structure determination limit. Some co-crystals are isostructural with their components. The non-fluoro as well as the halogeno-fluoro substituted components of co-crystals seem to impose their crystal structure on the complementary fluoro- or cyano-fluoro substituted components. Co-crystallization enhanced the deviation from centrosymmetry.