156713-49-4

Basic information

• Product Name: Anthracene, 1-(2-phenylethenyl)-, (Z)-
• CAS NO: 156713-49-4
• Molecular Formula: C22H16
• Molecular Weight: 280.369
• Mol File: 156713-49-4.mol

Chemical Properties

• CAS DataBase Reference: Anthracene, 1-(2-phenylethenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Anthracene, 1-(2-phenylethenyl)-, (Z)-(156713-49-4)
• EPA Substance Registry System: Anthracene, 1-(2-phenylethenyl)-, (Z)-(156713-49-4)

Safety Data

• Hazardous Substances Data: 156713-49-4(Hazardous Substances Data)

Upstream product

• 24463-14-7 1-(bromomethyl)anthracene 
• 100-52-7 benzaldehyde 
• 164263-16-5 4a,4b-dihydrobenzochrysene 
• 1140-79-0 anthracene-1-carbaldehyde 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 114020-31-4 trans-1-styrylanthracene 
• 214-17-5 Benzo[b]chrysene 

Relevant articles and documents

Photoisomerization and Photocyclization Reactions of 1-Styrylanthracene

On triplet sensitization, 1-styrylanthracene (1SA) undergoes adiabatic cis->trans one-way isomerization (3c*->3t*) similarly to 2-anthrylethylenes.However, upon direct irradiation, cis-1SA in the singlet excited state mostly undergoes cyclization to a dihydrophenanthrene-type product (DHP), 4a,4b-dihydrobenzochrysene, competing with an inefficient intersystem crossing to 3c* followed by one-way isomerization.The produced DHP, in deaerated benzene, is reverted to cis-1SA by a thermal (Ea = 14.9 kcal mol-1) or a photochemical pathway; however, under an oxygenated atmosphere DHP gives benzochrysene.A failure in the production of a cyclized product upon the excitation of trans-1SA shows that the isomerization really takes place in a one-way fashion.

Temperature effects on the photoreactivity and rotamerism of (Z)-1-styrylanthracene in non-polar and polar solvents

The photochemical and photophysical behaviour of (Z)-1-styrylanthracene (cis-1-StAn) has been investigated as a function of temperature and solvent polarity. In non-polar solvents above 260 K, cis-1-StAn mostly undergoes photocyclization to benzo[b]chrysene through an activated singlet pathway (18 kJ mol-1). The cis → trans photoisomerization occurs with very low quantum yield through an adiabatic mixed (singlet and triplet) mechanism above room temperature or through an adiabatic triplet mechanism below 260 K. Above room temperature, a second cyclization photoproduct was observed, formed from a different conformational isomer. The presence of conformational equilibria of cis-1-StAn in the ground and excited singlet states is also supported by the dependence of its spectral properties on temperature and by calculations. In polar solvents, the cis-→ trans photoisomerization, which occurs mainly through a diabatic singlet mechanism, is competitive with cyclization in the relaxation of the lowest excited singlet state.