54842-61-4

Upstream product

• 4546-04-7 tetraethyl 1,4-xylylenediphosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 106-42-3 para-xylene 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 1519-47-7 [p-phenylenebis(methylene)]bis[triphenylphosphonium] dichloride 
• 40817-03-6 p-xylenebis(triphenylphosphonium) dibromide 
• 52577-04-5 p-xylylene-α,α'-bis(phosphonic acid dimethyl ester) 
• 637-69-4 4-Methoxystyrene 
• 106-37-6 1.4-dibromobenzene 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 64984-68-5 (E,E)-1,4-bis(β-bromovinyl)benzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 696-62-8 para-iodoanisole 
• 6781-43-7 1,4-bis(1-hydroxyethyl)benzene 

Downstream Products

• 65614-67-7 4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(ethene-2,1-diyl)diphenol 
• 131941-36-1 1,4-bis ((4-methoxyphenyl)ethynyl)benzene 

Relevant academic research and scientific papers

A facile tandem double-dehydrative-double-Heck olefination strategy for pot-economic synthesis of (E)-distyrylbenzenes as multi-target-directed ligands against Alzheimer's disease employing C. elegans model

A concise, one pot and regioselective access to (E)-distyrylbenzenes (DSBs) from arylhalide and secondary phenylenediethanol, a stable precursor for in situ generation of divinylbenzene (DVB) to avoid its polymerization, is described for construction of double C–C bond formation via tandem double-dehydrative-double-Heck (D-D-D-H) reaction using Palladium and ionic liquid [hmim]Br as a cooperative catalyst. It is noteworthy that this pot-economy approach also provides direct synthesis of hydroxylated distyrylbenzenes without requirement of protection-deprotection strategy. Importantly, the synthesized DSBs are tested for their protective activity against β amyloid reduction, acetylcholine esterase inhibition, lipid lowering and reactive oxygen species (ROS) reduction properties in transgenic Caenorhabditis elegans model wherein 1,3-bis((E)-4-(trifluoromethyl)styryl)benzene (5c) is found to be active across all above factors thus presenting lead molecule within multi-target-directed ligands (MTDLs) approach. Molecular docking studies were also performed to understand the interactions of potent DSBs with receptors.

Phenylenevinylene oligomers by Mizoroki-Heck cross coupling reaction. Structural and optoelectronic characterization

In order to study the effect of the molecular structure on the optical properties of totally trans-trans phenylenevinylene oligomers (OPVs), sixteen 1,4-distyrylbenzene derivatives (1a-i and 2a-g) functionalized with different electron-donating (ED) and electron-withdrawing (EW) groups were synthesized by the Mizoroki-Heck cross coupling reaction in moderate to good yields (40–95%). The implemented methodology, with a small modification previously reported by our group, allows obtaining the desired vinyl configuration as well as one novel OPV compound (1h). After structural characterization by several techniques (e.g. FTIR, 1H, 13C and Solid-State NMR), particular emphasis was placed upon the investigation of their optical properties by UV–vis and fluorescence spectroscopies. The results showed that, with only one exception, the ED and EW groups at the ends of OPV systems lead to a bathochromic shift. This effect is intensified with the introduction of methoxy groups on the central ring. Consistent with these, the HOMO-LUMO gaps (ΔE) decreases as the strength of ED and EW substituents increases. The ED and EW substituents also lead to a decrease in the Φf values. This contribution in the area of organic electronics can be used as a reference to better select the most appropriate technological application for each OPV and this can be extrapolated to their respective structurally analogous segmented polymer.

Ruthenium-Sulfonamide-Catalyzed Direct Dehydrative Condensation of Benzylic C-H Bonds with Aromatic Aldehydes

The first catalytic dehydrative condensation of the benzylic C-H bonds of toluene and p-xylene with aromatic aldehydes is reported herein. This protocol provides highly atom-economical access to stilbene and p-distyrylbenzene derivatives, whereby water is the sole byproduct. The reaction is based on the deprotonation-functionalization of benzylic C-H bonds through η6-complexation of the arenes, which is realized for the first time using a catalytic amount of a transition metal activator. The key to the success of this method is the use of a sulfonamide anion as a catalyst component, which appears to facilitate not only the deprotonation of the benzylic C-H bonds but also the formation of a C-C bonds via an electrophilic tosylimine intermediate.

Iron-catalyzed cross-coupling reaction of aryl Grignard reagents with bis(2-bromovinyl)benzenes

Fe(acac)3 has been used as the catalyst in cross-coupling reactions of aryl Grignard reagents with 1, 4-bis(2-bromovinyl)benzenes affording bis(2-arylvinyl)benzenes. Effects of alkoxy substituents on both reactants and of the temperature on the

Polyfluorinated bis-styrylbenzene β-amyloid plaque binding ligands

β-Amyloid (Aβ) binding affinities and specificities for six bis-styrylbenzenes with multiple magnetically equivalent fluorine atoms in the form of a tetrafluorophenyl core or symmetrical trifluoromethyl and trifluoromethoxy groups were determined by means of fluorescence titrations with amyloid peptide Aβ1-40 and a novel in vitro fluorescence-based assay using APP/PS1 transgenic mouse brain sections. Bisstyrylbenzenes with a tetrafluorophenyl core had increased Aβ binding affinities compared to their monofluorophenyl or phenyl counterparts. Bis-styrylbenzenes with carboxylic acid functional groups had lower Aβ binding affinities than their neutral counterparts. Selected bis-styrylbenzenes were demonstrated to have good blood - brain barrier penetration capabilities. These data extend the SAR of bis-styrylbenzene Aβ binding and provide direction for the development of a noninvasive probe for early detection of Alzheimer's disease using 19F MRI.

Electronic and magnetic metal-metal interactions in dinuclear oxomolybdenum(V) complexes across bis-phenolate bridging ligands with different spacers between the phenolate termini: Ligand-centred vs. metal-centred redox activity

A series of dinuclear complexes has been prepared in which two {MoV(TpMe,Me)(O)Cl} fragments (abbreviated as Mo; TpMe,Me = tris(3,5-dimethylpyrazol-1-yl)hydroborate) are attached to either end of a bis-p-phenolate bridging ligand [(4,4′-OC6 H4)-X-(4,4′-C6H4O)]2-. The complexes are Mo2 (C=C)(X = CH=CH), Mo2(C=C)2 (X = CH=CH-CH=CH), Mo2(C=C)3 (X = CH=CH-CH=CH-CH=CH), Mo2(th) (X = 2,5-thiophenediyl), Mo2(th)2 (X = 2,5:2′,5′-bithiophenediyl), Mo2(th)3 (X = 2,5:2′,5′:2″,5″-terthiophenediyl), Mo2 (C≡C) (X = C≡C), Mo2(N=N) (X = N=N), Mo2(CO) [X = C(O)] and Mo2(C2ΦC2) [X = CH=CH(1,4-C6H4)CH=CH]. Electrochemical, UV/VIS/NIR spectroelectrochemical and magnetic measurements have been carried out in order to see how effectively the different spacer groups X mediate electronic and magnetic interactions between the two redox-active, paramagnetic, Mo centres. The electronic interactions were determined from the redox separation between the two successive one-electron oxidations which are formally Mo(VI)-Mo(V) couples; it was found that thienyl units in the bridging ligand are much more effective at maintaining electronic communication over long distances than p-phenylene or ethenyl spacers of comparable lengths. The azo (N=N) linkage afforded a much weaker electronic interaction than the ethenyl or ethynyl spacers. UV/VIS/NIR spectroelectrochemical studies showed that whereas the first oxidation is metal-centred to give Mo(VI)-Mo(V) species with characteristic intense phenolate→Mo(VI) LMCT transitions in the near-IR region, the spectra of the doubly oxidised complexes are characteristic of quinones: thus, the sequence of species formed on oxidation is [Mo(V)(μ-diolate)Mo(V)]0→[Mo(V)(μ-diolate)Mo(VI)] +→[Mo(V)(μ-quinone)Mo(V)]+2, with an internal charge redistribution associated with the second oxidation. Semi-empirical ZINDO calculations provide some support for this. Magnetic susceptibility measurements on Mo2(C=C), Mo2(th), Mo2(N=N) and Mo2(C≡C) show that all are weakly antiferromagnetically coupled, as expected on the basis of a spin-polarisation picture, with the order of strength of the magnetic interaction being the reverse of the order for electronic coupling, such that Mo2(th) affords the strongest electronic interaction but the weakest magnetic interaction.

Alkoxylated p-phenylenevinylene oligomers: Synthesis and spectroscopic and electrochemical properties

Twenty-one n-alkoxy substituted phenylenevinylene oligomers were synthesized, varying in size, number and position of the OR groups. IR,MS and solubility data are presented. NMR measurements provided the molecular structure as well as information about conformations and molecular dynamics. UV and of cyclic voltammetric data give correlations of chemical structure (number and position of OR substituents) with separate HOMO and LUMO energies.

Synthesis and Absorption/Emission Spectral Properties of Styrylstilbene and Distyrylanthracene Derivatives

A series of para-substituted styrylstilbenes I and 9,10-distyrylanthracenes II was synthesized by Wittig or Arbusov-Horner reaction as a key step.Subsequently, systematic investigations were carried out on their absorption and fluorescence spectra, and th