1080-74-6

Usage

Uses

Used in Polymer Solar Cell Industry:
3-(Dicyanomethylidene)indan-1-one is used as a building block for the preparation of non-fullerene acceptors (NFAs) such as ITIC, IHIC, IEIC, and IXIC. These NFAs are essential components in the development of highly efficient organic photovoltaic devices, which are crucial for the advancement of solar energy technology. The electron-deficient nature of 2HIC allows for improved charge transport and enhanced performance in polymer solar cells, making it a valuable asset in the renewable energy sector.

Upstream product

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

Downstream Products

• 137929-18-1 2-{2-[1-[2-(4-Diethylamino-phenylazo)-4-trifluoromethyl-thiazol-5-yl]-1-piperidin-1-yl-meth-(E)-ylidene]-3-oxo-indan-1-ylidene}-malononitrile 
• 131557-62-5 2-(4-methoxyphenyl)-8-dicyanovinylindeno(2,1-d)thiazole 
• 133149-38-9 3-amino-1-phenylfluorenone-2,4-dicarbonitrile 
• 109347-62-8 2-(2-{(Z)-4-[Bis-(2-hydroxy-ethyl)-amino]-phenylimino}-3-oxo-indan-1-ylidene)-malononitrile 
• 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 
• 109347-64-0 N-{2-[1-Dicyanomethylene-3-oxo-indan-(2Z)-ylideneamino]-5-diethylamino-phenyl}-acetamide 
• 109347-65-1 N-{2-[1-Dicyanomethylene-3-oxo-indan-(2Z)-ylideneamino]-5-dipropylamino-phenyl}-acetamide 
• 131919-19-2 2-{2-[1-(4-Diethylamino-phenyl)-meth-(Z)-ylidene]-3-oxo-indan-1-ylidene}-malononitrile 

Relevant academic research and scientific papers

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, optical and electrochemical properties of new thieno[2,3-b]indole-based dyes

Three new push-pull dyes consisting of a thieno[2,3-b]indole ring system as an electron donor, thiophene spacer as a π-bridge, and electron-withdrawing moieties such as 2-methylene malonitrile, 2-methylene-1Hindene- 1,3(2H)-dione, and 2-(2-methylene-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, have been synthesized and studied for their application in organic electronics devices. Investigation of their optical and electrochemical properties reveal that these compounds possess narrow band gaps (1.7-2 eV) and an effective absorption in the visible spectral range (440-740 nm). Therefore, these chromophores can be regarded as promising light-harvesting materials.

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.

Synthesis and chemosensing properties of indole based donor-π-acceptor dye material

In this work, we have designed and synthesized a new chemosensor for the detection of various metal ions. The chemosensor named 2-[2-(1 H-indole-2-ylmethylene)-3-oxo-indan-1-yliden]-malononitrile was synthesized using 3-formyl indole and 2-(3-oxo-indan-1-yliden)-malononitrile. This chemosensor has been investigated the properties which are able to detect and recognize the detection function of heavy metal ions. D-π-A system of dye chemosensor between electron withdrawing malononitrile and electron donating indole moieties provides the functions to interact with target metal ions. These recognizing sensing effects were studied using the absorption behaviors. Furthermore, cyclic voltammogram was used to determine HOMO/LUMO energy levels from their redox onset points. Measured energy levels of HOMO/LUMO were compared with computational calculation and discussed in details. Finally, the interaction type of metal ions binding was determined by Job's plot measurements.

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

A triphenylamine-containing donor-acceptor molecule for stable, reversible, ultrahigh density data storage

A triphenylamine-containing donor-acceptor molecule was designed and synthesized. Its thin film showed excellent bistable electronic switching behavior with a high ON/OFF current ratio. With this molecule, stable, reliable, and reversible ultrahigh densit

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

Non-fullerene electron acceptor material and organic photovoltaic cell

Disclosed are a non-fullerene electron acceptor material represented by formula (I) and an organic photovoltaic cell having an active layer comprising the aforementioned non-fullerene electron acceptor material. When the non-fullerene electron acceptor ma

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

Efficient near infrared D-π-A sensitizers with lateral anchoring group for dye-sensitized solar cells

A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an η value of 3.7% in the NIR region reported in DSCs.