24789-99-9

Usage

Uses

Used in Electronics Industry:
[4-(diethylamino)phenyl]ethylenetricarbonitrile is used as an electron transporting material for organic light-emitting diodes (OLEDs) due to its high electron mobility and efficiency in converting light into electricity.
Used in Photovoltaic Applications:
In the renewable energy sector, [4-(diethylamino)phenyl]ethylenetricarbonitrile is studied for its potential applications in organic photovoltaic devices, as it exhibits high electron mobility and efficiency in converting light into electricity, which can contribute to the development of more efficient solar panels.

InChI:InChI=1/C15H14N4/c1-3-19(4-2)14-7-5-12(6-8-14)15(11-18)13(9-16)10-17/h5-8H,3-4H2,1-2H3

Upstream product

• 19452-37-0 N,N-Diethylaniline hydroiodide 
• 205651-05-4 ethyl pentacyanocyclopropanecarboxylate 
• 670-54-2 ethenetetracarbonitrile 
• 91-66-7 N,N-diethylaniline 
• 139952-06-0 Hexacyanocyclopropane 
• 89745-73-3 tricyanovinyl bromide 
• 33342-62-0 chloroethene tricarbonitrile 
• 3189-44-4 2,2,1-tricyano-1-hydroxy-ethylene, tetramethyl-ammonium salt 

Downstream Products

• 1326216-12-9 2-(dimethylamino[(4-diethylaminophenyl)methylene])malononitrile 
• 1326216-11-8 2-[(4-diethylaminophenyl)(morpholin-4-yl)methylene]malononitrile 

Relevant academic research and scientific papers

TRICANOVINYLATION OF PHENOXAZINE AND PHENOTHIAZINE

In the reaction of tricynoethylene (TCE) with phenoxazine in DMF at 100 deg C, in addition to the principal reaction product - viz., 3-(tricynovinyl)phenoxazine - 3-dicyanomethylene-3H-phenoxazine and 3-phenoxazinyl-3-(3H-phenoxazinylene)-cyanomethane are formed in small amounts.The latter two compounds were also obtained from phenoxazine and dibromomalononitrile.Phenothiazine reacts similarly with tetracyanoethylene.A reaction scheme is proposed, and in this scheme the formation of side products is explained by significant electron transfer in the tetracyanoethylene-heterocycle system.For the first time, 1,6 cleavage of HCN was detected, in which (in contrast to the known 1,6 cleavage of HCN from carbon atoms) the hydrogen is split out from the nitrogen atom.

Fourier-transform infrared and optical absorption spectra of 4-tricyanovinyl-N,N-diethylaniline thin films

Thin films of 4-tricyanovinyl-N,N-diethylaniline (TCVA) were prepared for the first time using thermal evaporation technique. The molecular structure and electronic transitions of TCVA films were investigated by Fourier-transform infrared (FTIR) and ultraviolet-visible (UV-vis) spectra. The observed vibrational wavenumbers in FTIR spectra were analysed and assigned to different normal modes of the molecule. UV-vis electronic absorption spectral measurements of TCVA films were analysed to obtain the electronic transitions and optical band gap (Eg). Other important optical parameters such as molar extinction coefficient (εmolar), the oscillator strength (f), and the electric dipole strength (q2) were also reported.

Eco-friendly and recyclable media for rapid synthesis of tricyanovinylated aromatics using biocatalyst and deep eutectic solvent

An efficient and clean synthesis of aromatic tricyanovinyl compounds from nucleophilic reagent and tetracyanoethylene has been achieved using biocatalyst and deep eutectic solvent (DES). Reaction using biocatalyst and DES requires lesser reaction time than conventional method. The advantages of the present method are ambient reaction temperature, easy isolation of the product, higher yield, recyclability of the catalyst, and reactions without use of hazardous, volatile organic solvent. The DES as well as biocatalyst were recycled efficiently without any additional treatment. Synthesized compounds were also studied for UV-vis absorption and show solvatochromism.

Photophysical properties of arylcarbonitrile derivatives: Synthesis, absorption and emission spectra, and quantum chemical studies

A new series of aromatic cyanovinyl compounds were synthesized via one-pot reactions of tri- or tetracyanoethylenes with nucleophilic reagents. The ground-state geometries and UV-vis absorption spectra of the compounds were computationally analyzed by means of density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations, respectively. None of the compounds were fluorescent in solution, but some showed intense emission in the solid state. The first excited singlet states (S1) potential energy surfaces (PESs) were explored using complete active space SCF (CASSCF) calculations for the compounds in order to elucidate nonradiative decay mechanism that takes into account the involvement of conical intersections (CI).

An improved method for tricyanovinilation of aromatic amines under ultrasound irradiation

A synthetic method for tricyanovinylation under ultrasound irradiation has been developed for preparation of tricyanovinyl aromatic amines. The method is reliable and can be applied to the synthesis of a variety of tricyanovinyl compounds, with high yields, purity and with short reaction times.

Non-linear optically active molecules, their synthesis, and use

In one aspect, the present invention provides a hyperpolarizable organic chromophore. The chromophore is a nonlinear optically active compound that includes a π-donor conjugated to a π-acceptor through a π-electron conjugated bridge. In other aspects of the invention, donor structures and acceptor structures are provided. In another aspect of the invention, a chromophore-containing polymer is provided. In one embodiment, the chromophore is physically incorporated into the polymer to provide a composite. In another embodiment, the chromophore is covalently bonded to the polymer, either as a side chain polymer or through crosslinking into the polymer. In other aspects, the present invention also provides a method for making the chromophore, a method for making the chromophore-containing polymer, and methods for using the chromophore and chromophore-containing polymer.

Reaction of ethyl pentacyanocyclopropanecarboxylate with amines

Reaction of ethyl pentacyanocyclopropanecarboxylate with aliphatic amines yields the corresponding pentacyano-2-propen-1-ides, and in reaction with aromatic amines depending on the structure of the original amine arise N,N-dialkyl-4-(tricyanovinyl)anilines and bis(N,N-dialkylaminophenyl)malononitriles or ethyl 2-arylamino-1,2-dicyanoethene-1-carboxylates.

Reaction of polycyanocyclopropanes with amine hydroiodides

Reactions of ethyl 1,2,2,3,3-pentacyanocyclopropanecarboxylate, l,3-dioxoindan-2-spirocyclopropane-2′,2′,3′,3′- tetracarbonitrile, 2,4,6-trioxoperhydropyrimidine-5-spirocyclopropane-2′,2′,3′, 3′-tetracarbonitrile, and 4,4-dimethyl-2,6-dioxocyclohexanespirocyclopropane-2′,2′,3′, 3′-tetracarbonitrile with amine hydroiodides yield, depending on the structure of the initial cyclopropane, 1-ethoxycarbonyl-1,2,3,3-tetracyanopropenides, ethyl 3-arylamino-2,3-dicyanoacrylates, N,N-dialkyl-4-(tricyanovinyl)anilines, (4-dimethylaminophenyl)(1,3-dioxoindan-2-yl)malononitrile, (l,3-dioxoindan-2-yl)(4-tolylamino)malononitrile, 5-[aryl(dicyano)methyl]perhydropyrimidine-2,4,6-triones, and 2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4Hchromene-3,4,4-tricarbonitrile.

Hexacyanocyclopropane. II. Reaction of Hexacyanocyclopropane with Aliphatic and Aromatic Amine Hydroiodides

Reaction of hexacyanocyclopropane with aliphatic amine hydroiodides gives corresponding pentacyano-2-propen-1-ides and cyanogen iodide, whereas with aromatic amine hydroiodides unsubstituted and ring-substituted N-(tricyanovinyl)anilines or N,N-dialkyl-4-(tricyanovinyl)anilines, malononitrile, and iodine are formed.

Hexacyanocyclopropane. III. Reaction of Hexacyanocyclopropane with Aromatic Amines

Reaction of hexacyanocyclopropane with aromatic amines yields N- and C-tricyanovinylanilines. A mechanism of this reaction is proposed on the basis of stoichiometric ratios in the reactions of hexacyanocyclopropane and tetracyanoethylene oxide with aromatic amines.