1217-45-4

Usage

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

• 36856-11-8 C₁₆H₁₄N₄ 
• 546-67-8 lead(IV) tetraacetate 
• 17263-10-4 Anthracene-9,10-dicarbonitrile; compound with naphthalene 
• 51908-08-8 Anthracene-9,10-dicarbonitrile; compound with 2-methyl-naphthalene 
• 58964-23-1 Anthracene-9,10-dicarbonitrile; compound with 1,2,4,5-tetramethyl-benzene 
• 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 

Downstream Products

• 103510-72-1 10,10-dibenzyl-9-(4-chloro-benzyl)-9,10-dihydro-anthracene-9-carbonitrile 
• 103166-33-2 10,10-dibenzyl-9,10-dihydro-anthracene-9-carbonitrile 
• 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 

Relevant academic research and scientific papers

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.

Salt Effect for Accelerating Charge Separation from 9,10-Dicyanoanthracene-Stilbene Exciplex in Dichloromethane

On radiation of 9,10-dicyanoanthracene (DCA) in the presence of cis-(CS) and trans-stilbene (TS) in dichloromethane, addition of tetrabutylammonium tetrafluoroborate efficiently accelerated production of the radical cations from CS and TS along with DCA radical anions.

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.

Facile synthesis of cyanoarenes from quinones by reductive aromatization of cyanohydrin intermediates

A novel synthesis of cyanoarenes from quinones by using PCl3 as the reagent for reductive aromatization of cyanohydrin intermediates is reported. In situ IR spectroscopic measurements were conducted to monitor the reactions and to develop a convenient one-pot protocol. 1,4-Dicyanobenzene and 9,10-dicyanoanthracene were prepared by the new procedure.

Quantum amplified isomerization: A new concept for polymeric optical materials

The preparation and evaluation of a new class of photoresponsive polymers are described on the basis of a process called quantum amplified isomerization (QAI). The QAI process utilizes photoinitiated, cation radical isomerization chemistry in a polymeric medium. Two classes of materials are described: one where the QAI reactant is molecularly doped in the polymer matrix and another where the reactant is part of a functionalized polymer. Quantum yield experiments demonstrate that the isomerization reaction can proceed by a chain process with modest efficiencies. Photochemical conversion experiments show that high extents of conversion of the QAI reactants are possible. The rate and extent of conversion are strongly correlated to the glass transition temperature of the polymer. For molecularly doped polymers, hypotheses to explain the high conversions based on diffusion or phase separation of the reactants were tested and excluded. Models are discussed to rationalize experimental factors that affect the quantum yields and the photochemical conversions.

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.

Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials

We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.

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.

Preparation of (1R,1′R)-1,1′-(anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine): a chiral diamine with low basicity

A new chiral diamine with low basicity was synthesized in enantiopure form. (1R,1′R)-1,1′-(Anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine) was obtained by means of several stereochemically controlled reactions. The structures of the title compound and several intermediates were studied.

An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid

Aryl and arylvinyl nitriles have been prepared in good yields from the corresponding bromides with potassium hexacyanoferrate (II) using palladium-catalyzed reactions in ionic liquid under microwave irradiation. Georg Thieme Verlag Stuttgart.