1254-43-9

Basic information

• Product Name: Anthracene, 9,10-bis(2-phenylethenyl)-
• CAS NO: 1254-43-9
• Molecular Formula: C30H22
• Molecular Weight: 382.505
• Mol File: 1254-43-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Anthracene, 9,10-bis(2-phenylethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Anthracene, 9,10-bis(2-phenylethenyl)-(1254-43-9)
• EPA Substance Registry System: Anthracene, 9,10-bis(2-phenylethenyl)-(1254-43-9)

Safety Data

• Hazardous Substances Data: 1254-43-9(Hazardous Substances Data)

Upstream product

• 120-12-7 anthracene 
• 34373-96-1 9,10-dibromomethylanthracene 
• 100-52-7 benzaldehyde 
• 60974-92-7 tetraethyl (anthracene-9,10-diylbis(methylene))bis(phosphonate) 
• 100-42-5 styrene 
• 523-27-3 9,10-Dibromoanthracene 
• 536-74-3 phenylacetylene 
• 121676-74-2 9-<Δ¹-Cyclohexenyl-ethinyl>-10-phenylethinyl-9,10-dihydroxy-9,10-dihydro-anthracen 
• 71-41-0 pentan-1-ol 
• 859331-73-0 9-(α,β-dichloro-styryl)-10-phenylethynyl-anthracene 
• 119571-31-2 9-(Δ¹-Cyclohexenyl-ethinyl)-10-phenylethinyl-anthracen 

Relevant articles and documents

Light-Harvesting Organic Nanocrystals Capable of Photon Upconversion

Harvesting and converting low energy photons into higher ones through upconversion have great potential in solar energy conversion. A light-harvesting nanocrystal assembled from 9,10-distyrylanthracene and palladium(II) meso-tetraphenyltetrabenzoporphyrin as the acceptor and the sensitizer, respectively effects red-to-green upconversion under incoherent excitation of low power density. An upconversion quantum yield of 0.29±0.02 % is obtained upon excitation with 640 nm laser of 120 mW cm?2. The well-organized packing of acceptor molecules with aggregation-induced emission in the nanocrystals dramatically reduces the nonradiative decay of the excited acceptor, benefits the triplet–triplet annihilation (TTA) upconversion and guides the consequent upconverted emission. This work provides a straightforward strategy to develop light-harvesting nanocrystals based on TTA upconversion, which is attractive for energy conversion and photonic applications.

Why triple bonds protect acenes from oxidation and decomposition

An experimental and computational study on the impact of functional groups on the oxidation stability of higher acenes is presented. We synthesized anthracenes, tetracenes, and pentacenes with various substituents at the periphery, identified their photooxygenation products, and measured the kinetics. Furthermore, the products obtained from thermolysis and the kinetics of the thermolysis are investigated. Density functional theory is applied in order to predict reaction energies, frontier molecular orbital interactions, and radical stabilization energies. The combined results allow us to describe the mechanisms of the oxidations and the subsequent thermolysis. We found that the alkynyl group not only enhances the oxidation stability of acenes but also protects the resulting endoperoxides from thermal decomposition. Additionally, such substituents increase the regioselectivity of the photooxygenation of tetracenes and pentacenes. For the first time, we oxidized alkynylpentacenes by using chemically generated singlet oxygen (1O2) without irradiation and identified a 6,13-endoperoxide as the sole regioisomer. The bimolecular rate constant of this oxidation amounts to only 1 × 10 5 s-1 M-1. This unexpectedly slow reaction is a result of a physical deactivation of 1O2. In contrast to unsubstituted or aryl-substituted acenes, photooxygenation of alkynyl-substituted acenes proceeds most likely by a concerted mechanism, while the thermolysis is well explained by the formation of radical intermediates. Our results should be important for the future design of oxidation stable acene-based semiconductors.