89510-60-1

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 1253-47-0 triphenyl-(4-methoxycarbonylbenzyl)phosphonium chloride 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 14295-52-4 4-(diethyoxyphosphorylmethyl)benzoic acid methyl ester 
• 1076-96-6 methyl 4-vinylbenzoate 
• 80350-66-9 4-(bromobuta-1,3-dien-1-yl)benzene 
• 90766-67-9 1,1-dibromo-4-phenyl-1,3-butadiene 
• 619-44-3 methyl 4-iodobenzoate 
• 188802-38-2 ((1E,3E)-4-bromobuta-1,3-dienyl)benzene 

Downstream Products

• 654053-66-4 3-methyl-5-{4-[4-phenylbuta-1E,3E-dienyl]phenyl}penta-2E,4E-dienal 
• 52010-91-0 4-((1E,3E)-4-phenylbuta-1,3-dienyl)benzaldehyde 

Relevant academic research and scientific papers

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Bacteriorhodopsin Analogs from Diphenylpolyene Chromophores

Chromophore-modified bacteriorhodopsin (bR) analogs are prepared, to study the nature of chromophore-protein interaction as well as to develop new bR analogs that can find applications as photoactive element in molecular electronic devices. This article describes the preparation and characterization of hitherto unknown bR analogs based on diphenylpolyene chromophores. Diphenylpolyene compounds, namely, 4-[(E)-2-phenylvinyl]benzaldehyde (1), 3-methyl-5-{4-[(E)-2-phenylvinyl]phenyl}penta-2E,4E-dienal (2), 4-[4-phenylbuta-1E,3E-dienyl]benzaldehyde (3) and 3-methyl-5-{4-[4-phenylbuta-1E,3E-dienyl]phenyl}penta-2E,4E-dienal (4), have been synthesized, and their interaction with bacterioopsin (bOP) has been studied. Whereas aldehydes 2 and 4 interact with bOP and yield bR analogs bR-2 and bR-4, aldehydes 1 and 3 do not yield any pigment. Analogs bR-2 and bR-4 have been characterized for their opsin shift, competitive binding, photochemical properties and fluorescence spectral behavior.

Palladium-Catalyzed Syntheses of Aryl Polyenes

The palladium-catalyzed arylation reaction has been employed to prepare a variety of mono- and diaryl 1,3-dienes and 1,3,5-trienes.The yields were good when electron withdrawing substituents were present in the aryl groups but only poor to fair when electron-donating groups were involved.Monoaryl dienes and trienes reacted well with all types of aryl halides to give mixed diaryl derivatives. 2-Bromostyrene reacts with phenylhexatriene to form 1,8-diphenyloctatetraene and with hexatriene to form 1,10-diphenyldecapentaene, but both only in about 15percent yield.