1361119-48-3

Basic information

• Product Name: 9,10-bis(4-formylphenylethynyl)anthracene
• Synonyms: 9,10-bis(4-formylphenylethynyl)anthracene
• CAS NO: 1361119-48-3
• Molecular Weight: 434.494
• Mol File: 1361119-48-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 9,10-bis(4-formylphenylethynyl)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-bis(4-formylphenylethynyl)anthracene(1361119-48-3)
• EPA Substance Registry System: 9,10-bis(4-formylphenylethynyl)anthracene(1361119-48-3)

Safety Data

• Hazardous Substances Data: 1361119-48-3(Hazardous Substances Data)

Upstream product

• 18750-95-3 9,10-bis(trimethylsilyl)ethynylanthracene 
• 120-12-7 anthracene 
• 18512-55-5 9,10-diethynylanthracene 
• 1122-91-4 4-bromo-benzaldehyde 
• 523-27-3 9,10-Dibromoanthracene 
• 63697-96-1 4-Ethynylbenzaldehyde 

Downstream Products

• 1361119-51-8 9,10-bis(4-formylphenylethynyl)-9,10-dihydro-9,10-epidioxidoanthracene 

Relevant articles and documents

The relationship between molecular structure and electronic properties in dicyanovinyl substituted acceptor-donor-acceptor chromophores

In this contribution we describe a combined experimental and theoretical study of the relation between the molecular structure and the electronic properties of conjugated donor-acceptor type chromophores for light-harvesting applications. A series of model systems was synthesized where a central anthracene (electron donor) is connected to dicyanovinyl units (electron acceptor) through a π-conjugated spacer. The study of the redox and optical properties of these chromophores and of reference compounds without dicyanovinyl units allows us correlate the electronic properties to the presence of the electron withdrawing groups and the molecular conformation. Comparison with calculated electronic structure shows that the construction of chromophores that consist of electron donating and accepting units does not always follow the simple rules that are generally used in the design of such molecules. The results show a subtle relation between the charge transfer character and the geometry of the molecules. In some cases this leads to significant contribution of charge transfer excitation to the absorption spectra of some chromophores while such contributions are completely absent in others.

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.