1217-45-4

Basic information

• Product Name: 9,10-DICYANOANTHRACENE
• Synonyms: 9,10-Dicyanoanthracen;RARECHEM AQ BD AN07;9,10-DICYANOANTHRACENE;9,10-ANTHRACENEDICARBONITRILE;ANTHRACENE-9,10-DICARBONITRILE;DCA;DCAsensitizer;9,10-ANTHRACENEDICARBONITRILE 99%
• CAS NO: 1217-45-4
• Molecular Formula: C₁₆H₈N₂
• Molecular Weight: 228.25
• Product Categories: Aromatic Nitriles;Anthracenes
• Mol File: 1217-45-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 340 °C(lit.)
• Boiling Point: 360.06°C (rough estimate)
• Flash Point: 247.8 °C
• Appearance: yellow to golden yellow needles or powder
• Density: 1.2027 (rough estimate)
• Vapor Pressure: 1.16E-09mmHg at 25°C
• Refractive Index: 1.5635 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1646384
• CAS DataBase Reference: 9,10-DICYANOANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DICYANOANTHRACENE(1217-45-4)
• EPA Substance Registry System: 9,10-DICYANOANTHRACENE(1217-45-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-24/25
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1217-45-4(Hazardous Substances Data)

Usage

Description

9,10-Dicyanoanthracene, also known as 9,10-Anthracenedicarbonitrile (DCA, ADC), is an anthracene derivative characterized by the presence of cyano groups at positions 9 and 10. It is a yellow to golden yellow crystalline solid or powder, known for its photochemical properties and participation in various chemical reactions.

Uses

Used in Photochemistry Research:
9,10-Dicyanoanthracene is used as a photosensitizer for investigating the photoisomerization of trans-stilbene (TS) in sodium dodecyl sulfate (SDS)/benzyl alcohol (BA)/H2O systems. Its photochemical properties make it a valuable compound for studying the behavior of other molecules under light exposure.
Used in Chemical Reactions:
9,10-Dicyanoanthracene participates in the generation of nucleophilic α-hydroxymethyl radicals from α-silyl ethers by irradiation. This application highlights its role in facilitating specific chemical transformations, which can be useful in the synthesis of various organic compounds.
Used in Material Science:
The binding energy of 9,10-anthracenedicarbonitrile adsorbed onto graphene is -1.23eV, indicating its potential use in the development of novel materials with enhanced electronic properties. This characteristic can be exploited in the design of advanced materials for various applications, such as energy storage or electronic devices.

Purification Methods

Recrystallise the dinitrile twice from pyridine [Mattes & Farid J Am Chem Soc 108 7356 1986]. [Beilstein 9 IV 3667.]

InChI:InChI=1/C16H8N2/c17-9-15-11-5-1-2-6-12(11)16(10-18)14-8-4-3-7-13(14)15/h1-8H

Upstream product

• 58964-22-0 Anthracene-9,10-dicarbonitrile; compound with 1,2,3,4,5-pentamethyl-benzene 
• 17263-12-6 Anthracene-9,10-dicarbonitrile; compound with 1,2,3,4,5,6-hexamethyl-benzene 
• 17263-09-1 Anthracene-9,10-dicarbonitrile; compound with phenanthrene 
• 151-50-8 potassium cyanide 
• 642-31-9 9-anthracene aldehyde 
• 523-27-3 9,10-Dibromoanthracene 
• 544-92-3 copper(I) cyanide 
• 1104003-75-9 (E,E,Ss,Ss)-N,N'-(anthracene-9,10-diylbis(methan-1-yl-1-ylidene))bis(2-methylpropane-2-sulfinamide) 
• 7044-91-9 9,10-diformylanthracene 
• 58964-23-1 Anthracene-9,10-dicarbonitrile; compound with 1,2,4,5-tetramethyl-benzene 
• 51908-08-8 Anthracene-9,10-dicarbonitrile; compound with 2-methyl-naphthalene 

Downstream Products

• 86-73-7 fluorene radical cation 
• 91-20-3 Naphthalene 
• 92-52-4 biphenyl 
• 84-65-1 9,10-phenanthrenequinone 
• 65-85-0 benzoic acid 
• 1210-12-4 9-cyanoanthracene 
• 1467-01-2 9-cyano-10-methylanthracene 
• 14789-44-7 10-amino-9-anthracenecarbonitrile 
• 23353-77-7 10-Diethylaminomethyl-anthracene-9-carbonitrile 
• 613-33-2 4,4'-dimethylbiphenyl radical cation 
• 612-75-9 3,3'-dimethylbiphenyl radical cation 
• 2531-84-2 2-methyl phenanthrene radical cation 
• 56888-48-3 5-benzylbenzene-1,2,4-tricarbonitrile 
• 123621-31-8 cis/trans-9-benzyl-9,10-dicyano-9,10-dihydroanthracene 

Relevant articles and documents

Solvent Effects on Photoinduced Electron-Transfer Reactions

Dependence of the fluorescence-quenching rate constant kq, effective quenching distance rq, and free radical yield ΦR on the free enthalphy change ΔGf of full electron transfer has been studied in dichloromethane by using anthracenecarbonitrile as electron-accepting fluorescers and amino- and methoxybenzenes as electron-donating quenchers.On the basis of the present data in dichloromethane and the previous data in acetonitrile, the solvent effects on the electron-transfer fluorescence-quenching mechanism and on the back electron-transfer reaction within the geminate radical ion pairs are elucidated.

A pcu-type metal-organic framework with spindle [Zn7(OH) 8]6+ cluster as secondary building units

The in situ solvothermal reaction of 9,10-dicyanoanthracene and ZnCl 2/NaN3 gave the complex, {[Zn7(OH) 8(DTA)3]·H2O}n (1) (DTA 2- = 9,10-ditetrazolateanthracene), which presents a pcu-type topological framework formed by DTA2- bridging unprecedented heptanuclear spindle [Zn7(OH)8]6+ clusters as SBUs, and exhibits strong luminescent emission with long lifetime. The Royal Society of Chemistry.

Surprising differences in the reactivity of cyanoaromatic radical anions generated by photoinduced electron transfer

-

Steric Effects in Photoinduced Electron-Transfer Reactions

Quantum yields for formation of separated radical ions are determined for the electron-transfer reactions of singlet excited cyanoanthracene acceptors with sterically hindered alkylbenzene donors, in acetonitrile.These yields are up to 4 times larger than those for unhindered alkylbenzene donors.The yields are controlled by the competition between separation and return electron transfer in the initially formed radical-ion pairs.From studies of the dependence of the steric effect on the driving force for return electron transfer, it is concluded that the main effect of the steric hindrance is to decrease the magnitude of the electronic coupling matrix element for electron transfer, thus decreasing the return electron transfer rate and increasing the separation yield.The sterically hindered donors can be divided into two groups depending upon whether the substituents on the benzene ring have hydrogens that are capable of hyperconjugative stabilization of the positive charge in the radical cation.The electron transfer reorganization parameters are measurably different for the donors that have these substituents compared to those that lack such hydrogen atoms.

A Versatile One-Pot Access to Cyanoarenes from ortho- and para-Quinones: Paving the Way for Cyanated Functional Materials

A generally applicable direct synthesis of cyanoarenes from quinones is presented. Particular emphasis is placed on the preparation of precursors and target molecules relevant for organic materials, including halogenated cyanoarenes and larger cyanated acenes. The reaction and work-up protocols are adjusted for the challenges presented by the different substrates and products. Screening results of the initial reaction optimization are given to further facilitate adaptation to other synthetic problems. The universality of the reaction is finally highlighted by successful substitution of para-quinones by an ortho-quinone as the starting material.