1080-74-6

Basic information

• Product Name: 3-(DICYANOMETHYLIDENE)INDAN-1-ONE
• Synonyms: 3-(DICYANOMETHYLIDENE)INDAN-1-ONE;3-(DICYANOMETHYLIDENE)INDIAN-1-ONE;3-(Dicyanomethylene)indian-1-one;Dicyanomethyleneindianone;3-(Dicyanomethlidene)indan-1-one;3-(DICYANOMETHYLIDENE)INDAN-1-ONE 98+%;(1-Oxoindan-3-ylidene)malononitrile;(2,3-Dihydro-3-oxo-1H-indene-1-ylidene)malononitrile
• CAS NO: 1080-74-6
• Molecular Formula: C₁₂H₆N₂O
• Molecular Weight: 194.19
• Mol File: 1080-74-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 228 °C
• Boiling Point: 398.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.351±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-(DICYANOMETHYLIDENE)INDAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(DICYANOMETHYLIDENE)INDAN-1-ONE(1080-74-6)
• EPA Substance Registry System: 3-(DICYANOMETHYLIDENE)INDAN-1-ONE(1080-74-6)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1080-74-6(Hazardous Substances Data)

Usage

Description

3-(Dicyanomethylidene)indan-1-one (2HIC) is electron deficient thus electron withdrawing. It is used as a building block to prepare non-fullerene acceptors (NFAs) such as ITIC, IHIC, IEIC, IXIC for highly efficient organic photovoltaic devices.

Uses

3-(Dicyanomethylidene)indan-1-one is used in the preperation of polymer solar cells.

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 109-77-3 malononitrile 

Downstream Products

• 133149-38-9 3-amino-1-phenylfluorenone-2,4-dicarbonitrile 
• 136000-79-8 (1-Dicyanomethyl-3-oxo-indan-1-yl)-phosphonic acid dimethyl ester 
• 131573-58-5 8-dicyanovinylindeno(2,1-d)thiazole-2-acetonitrile 
• 133149-40-3 3-Amino-1-(4-chloro-phenyl)-9-oxo-9H-fluorene-2,4-dicarbonitrile 
• 109347-57-1 2-{2-[1-(3,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-3-oxo-indan-1-ylidene}-malononitrile 
• 133149-39-0 3-Amino-1-(4-methoxy-phenyl)-9-oxo-9H-fluorene-2,4-dicarbonitrile 
• 1402920-69-7 C₃₃H₂₆N₆O₂S 

Relevant articles and documents

Some Reactions with Indane-1,3-dione: A Facile Synthesis of Pentacycline Heterocyclic Analogues

Indane-1,3-dione 1 reacts with salicylaldehyde 5 and malononitrile 3 to afford 6-amino-7-imino-7H-indeno-[2′,1′:5,6]-pyrano-[3,4-c]-chromene 6, which could be transformed into the corresponding 7-oxo derivative 7. 2-(3-Oxoindan-1-ylidene)-malononitrile 10 couples with the diazonium salts 8, 14, and 15 to afford after cyclization the indeno-[2,1-c]-pyridazine 13 and the indeno-[2′,1′:3,4]-pyridazino-[1,6-a]-quinazoline derivatives 20 and 21, respectively.

Synthesis of novel push-pull chromophores based on N-ethylcarbazole for vacuum deposition processed organic photovoltaics

Two novel p-type materials, Cz(Et)ThOM and Cz(Et)OM - respectively with and without a thiophene π-spacing unit - have been synthesized for vacuum-deposited organic photovoltaics (OPVs). The power conversion efficiencies of planar heterojunction OPVs of the former are clearly higher than that of the latter. Further improvement of the device with Cz(Et)ThOM was obtained by employing bulk heterojunction structure and post-annealing. The structural analysis of thin films by synchrotron X-ray diffraction and atomic force microscopy shows that this improvement is due to Cz(Et)ThOM becoming highly ordered during annealing.

Naphthyl derivatives functionalised with electron acceptor units - Synthesis, electronic characterisation and DFT calculations

A series of unsymmetrical dyes containing a naphthyl unit connected to an electron acceptor moiety was designed and synthesised. By modifying the electron acceptor unit, a shift of the LUMO energy level as well as its distribution through the molecule were achieved. These dyes were fully characterised by optical, computational and electrochemical techniques. In addition, crystal structures reveal different packing depending upon the nature of the acceptor. Their potential use as electron acceptor materials for organic photovoltaics (OPVs) was also investigated by photoluminescence studies of blends with the common OPV polymers P3HT and PCDTBT. A series of unsymmetrical dyes was synthesised and characterised. Their optical and electrochemical properties were tuned by modifying the electron acceptor unit. Copyright

Non-fullerene electron acceptor material and organic photovoltaic cell

The invention provides a non-fullerene electron acceptor material represented by formula (I), and an organic photovoltaic cell having an active layer comprising the non-fullerene electron acceptor material. When the non-fullerene electron acceptor materia

A-D-A-D-A type organic micromolecular solar cell donor materials, and preparation method and application thereof

The invention provides organic micromolecular donor materials adopting 2,1,3-benzoselenadiazole and 3-(dicyanomethylidene)indan-1-one as electron acceptor units and triphenylamine as an electron donorunit, a preparation method thereof, and an application