10273-66-2

Basic information

• Product Name: 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl)bis(methylbenzene)
• Synonyms: 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl)bis(methylbenzene)
• CAS NO: 10273-66-2
• Molecular Weight: 370.491
• Mol File: 10273-66-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl)bis(methylbenzene)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl)bis(methylbenzene)(10273-66-2)
• EPA Substance Registry System: 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl)bis(methylbenzene)(10273-66-2)

Safety Data

• Hazardous Substances Data: 10273-66-2(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 51560-21-5 1,4-diiodo-2,5-dimethoxybenzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 150-78-7 1,4-dimethoxybezene 
• 3752-97-4 1,4-bis(chloromethyl)-2,5-dimethoxybenzene 
• 3762-25-2 diethyl 4-methylbenzylphosphonate 
• 7310-97-6 2,5-dimethoxyterephthalaldehyde 
• 10273-64-0 1,4-bis(triphenylphosphoniomethyl)-2,5-dimethoxybenzene dichloride 

Relevant articles and documents

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.

Solid state behaviour of vinyl quinones

2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 angstrom stacking axis are also photoreactive.