28286-88-6

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Chemical Properties

White Powder

InChI:InChI=1/C10H8N2O/c1-7-3-9(4-8(2)13-7)10(5-11)6-12/h3-4H,1-2H3

Upstream product

• 109-77-3 malononitrile 
• 1004-36-0 2,6-dimethylpyrone 
• 4341-85-9 malonitrile 
• 520-45-6 Dehydracetic acid 
• 1004-37-1 2,6-dimethyl-pyran-4-thione 
• 108-24-7 acetic anhydride 

Downstream Products

• 70503-12-7 2-(2-Methyl-6-{(E)-3-[3-methyl-3H-benzooxazol-(2Z)-ylidene]-propenyl}-pyran-4-ylidene)-malononitrile 
• 70503-13-8 2-(2-Methyl-6-{(E)-3-[3-methyl-3H-benzothiazol-(2Z)-ylidene]-propenyl}-pyran-4-ylidene)-malononitrile 
• 70503-10-5 4-dicyanomethylene 2-<3-(1-ethyl-1H-quinolin-2-ylidene)-1-propenyl>-6-methyl-4H-pyran 
• 119438-04-9 DCM-OH 
• 119438-03-8 DCM-H 
• 119455-97-9 DCM-crown 
• 51325-91-8 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 863406-57-9 4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine-N-(3-[N,N-dimethylamino]-propane) 
• 403830-93-3 4-dicyanomethylene-2,6-dimethyl-1,4-dihydropyridine-N-ethane-2-ol 
• 791074-93-6 E,E-4-dicyanomethylene-2,6-bis-p-N,N'-n-butyl-N,N'-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)-aminostyrylpyran 
• 1128210-84-3 (E)-2-(2-(4-((2-hydroxyethyl)(methyl)amino)styryl)-6-methyl-4H-pyran-4-ylidene)malononitrile 

Relevant academic research and scientific papers

Design, synthesis and properties of a reactive chromophoric/fluorometric probe for hydrogen peroxide detection

As the most important starting material and degradation product of peroxide explosives, H2O2 is considered as a signature compound for peroxide-based explosives. A new probe, (2-(2,6-bis((E)-2-(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)vinyl)-4H-pyran-4-ylidene)malononitrile) (AVPM), for both chromophoric/fluorometric detection of H2O2 was designed and synthesized. AVPM emitted a long wavelength emission from its intramolecular charge transfer (ICT) and hence its absorption was expanded to the visible region. The response rate and sensitivity of AVPM for H2O2 detection were tremendously improved (91% of the fluorescence was quenched within 2 min for H2O2) by adding triethylamine (TEA) into the probe solution. And the solution color changed from yellow to blue. A detection limit down to 17.58 nM is remarkably achieved. These features lead to a new chromophoric/fluorometric probe for H2O2 detection and make it an ideal candidate for chemical detection and analysis in public safety and environmental monitoring.

Emission color tuning with polymer molecular weight for dyes of 4-dicyanomethylene-2-methyl-6-{4-[(2-hydroxyethyl)(methyl)amino]styryl}-4H-pyran

A series of novel polylactide (PLA) polymers were synthesized initiated by 4-dicyanomethylene-2-methyl-6-{4-[(2-hydroxyethyl)(methyl)amino]styryl} -4H-pyran (DCM) with Sn(Oct)2 as catalyst. The color and emission of the polymer can be tuned just with polymer molecular weight. A series of novel polylactide (PLA) polymers were synthesized initiated by 4-dicyanomethylene-2- methyl-6-(4-((2-hydroxyethyl)(methyl)amino)styryl)-4H-pyran (DCM) and the color and emission of the polymer can be tuned just with polymer molecular weight. Copyright

Tuning optical absorption in pyran derivatives for DSSC

Four nobel metal free dyes for application as photosensitizers in DSSC have been synthesized and their chemical-physical properties characterized by UV-vis absorption spectroscopy, cyclic voltammetry and DFT theoretical computations. The dyes are based on a pyran core, functionalized with different electron acceptor groups, symmetrically linked to carbazole electron donor mojeties. The four dyes have different optical absorption properties, affording a range of colors ranging from orange to blue, covering most of the visible spectral region. All the dyes feature high molar extinction coefficient, up to a value of 1.0 × 105 L mol-1 cm-1. The dyes were used as photosensitizers in DSSC and the photovoltaic characterization of these devices was performed under simulated solar radiation. The cell performance is higher for chromophores featuring higher LUMO energies as a consequence of a better electron injection in TiO2 oxide. A maximum power conversion efficiency of 1.9% has been achieved.

A Novel Bat-Shaped Dicyanomethylene-4H-pyran-Functionalized Naphthalimide for Highly Efficient Solution-Processed Multilevel Memory Devices

Small-molecule-based multilevel memory devices have attracted increasing attention because of their advantages, such as super-high storage density, fast reading speed, light weight, low energy consumption, and shock resistance. However, the fabrication of small-molecule-based devices always requires expensive vacuum-deposition techniques or high temperatures for spin-coating. Herein, through rational tailoring of a previous molecule, DPCNCANA (4,4′-(6,6′-bis(2-octyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-9H,9′H-[3,3′-bicarbazole]-9,9′-diyl)dibenzonitrile), a novel bat-shaped A-D-A-type (A-D-A=acceptor–donor–acceptor) symmetric framework has been successfully synthesized and can be dissolved in common solvents at room temperature. Additionally, it has a low-energy bandgap and dense intramolecular stacking in the film state. The solution-processed memory devices exhibited high-performance nonvolatile multilevel data-storage properties with low switching threshold voltages of about ?1.3 and ?2.7 V, which is beneficial for low power consumption. Our result should prompt the study of highly efficient solution-processed multilevel memory devices in the field of organic electronics.

Design, synthesis and characterization of ferrocene based V-shaped chromophores with modified nonlinear effect

In order to prepare D-π-A-π-D analogs have the ability to use in optical applications, 4H-pyran fragment conjugated with two styryl groups and their combination play π-spacer role between donor and acceptor groups. Malononitrile and 1, 3-indandione play as acceptor groups and ferrocene nuclei was chosen as donor group. 1H and 13C NMR, FT-IR and mass spectroscopy and CHN analysis were used to confirm the structure of synthesized compounds. Electrochemical, photochemical and photophysical properties of these compounds were studied. The third order nonlinear refractive index, n2, and nonlinear absorption coefficient, β, of synthesized chromophores were assessed by the open and closed aperture Z-scan measurements, respectively. The quantum chemistry study was performed on synthesized compounds with the DFT approach. The theoretical and experimental results show that these compounds can be considered as candidates to be used in optical applications.

Novel pyran based dyes for application in dye sensitized solar cells

A class of novel pyran based chromophores has been synthesized and characterized for what concerns their optical and electrochemical properties. The electronic structures were investigated in details by means of DFT theoretical computations. The molecular structures of the chromophores are based on a pyran core, functionalized with different electron acceptor groups, symmetrically linked to phenothiazine electron donor moieties. The dyes have different optical absorption properties, affording a set of colors ranging from orange to blue, covering most of the visible spectral region and they are characterized by high molar extinction coefficient, up to a value of 6.4·104 cm-1 M-1. The dyes were used as photosensitizers in DSSC and the photovoltaic characterization of these devices was performed under simulated solar radiation. A maximum efficiency of 2.82% has been achieved. The most promising device underwent an accelerated ageing test, performed at 85 °C for 50 days: no variation of the main electrical parameters of the DSSC was observed during the test, indicating an excellent stability for devices based on this class of photosensitizers.

Two-photon pumped emission of polymeric thin film doped with dicyanopyranone derivative

Two-photon pumped up-conversion emission of polymeric thin film doped with an organic fluorophore dye (1) is described. It is found that 1 exhibits strong two-photon pumped up-conversion emission in polymeric thin film, and the mechanism shows that the up-conversion emission results from efficient two-photon absorption.

A red-emitting fluorescent probe with large Stokes shift for real-time tracking of cysteine over glutathione and homocysteine in living cells

Fluorescent probes with high quality for highly selective detection of cysteine (Cys) are still urgently in demand because of the indispensable roles Cys plays in the biological systems. Herein, a red-emitting fluorescent probe CP was developed for the highly selective detection of Cys over glutathione (GSH) and homocysteine (Hcy) by incorporating acryloyl group as the recognition unit into the 2-(2-(4-hydroxystyryl)-6-methyl-4H-pyran-4-ylidene) malononitrile (P-OH) fluorophore which is characterized by red emission, noteworthy Stokes shift, and appreciable photostability. Basically, CP demonstrated appreciable sensing performance toward Cys including short response time of 4 min, high sensitivity with approximately 147-fold emission enhancement, low detection limit of 41.696 nM, and good selectivity both in the solution and living cells, indicating its promising potential of visualizing Cys in biological systems.

Near-infrared luminous triphenylamine derivative fluorescent molecule as well as preparation method and application thereof

The invention provides a near-infrared luminous triphenylamine derivative fluorescent molecule as well as a preparation method and application thereof. The structural formula of the triphenylamine derivative fluorescent molecule is shown as a formula I which is described in the specification. The near-infrared fluorescent molecule has relatively large Stokes displacement and near-infrared fluorescence emission signals; and besides, the preparation method of the molecule is simple and high in designability, can effectively guide the design and synthesis of near-infrared fluorescent functional molecule, and has important application prospects in the field of disease diagnosis and treatment. In the formula I, X is as shown in the specification.

4-cyano-7, 8-dihydroisoquinoline derivative as well as preparation method and application thereof

The invention relates to the technical field of organic synthesis, in particular to a 4-cyano-7, 8-dihydroisoquinoline derivative as well as a preparation method and application thereof. According to the invention, symmetric and asymmetric dicyanomethylene-4H-pyran derivatives and secondary amine are used as raw materials, and a series of 4-cyano-7, 8-dihydroisoquinoline derivatives are prepared through ring opening and continuous ring closing reactions; and the reaction has the advantages of easily available raw materials, mild reaction conditions, wide substrate range, high yield and the like, is simple to operate, and avoids the defects of tedious steps, harsh reaction conditions, use of toxic and expensive metal catalysts and the like in conventional isoquinoline compound construction. The preparation method provides new possibilities for design and synthesis of isoquinoline molecules and application of the isoquinoline molecules in solid-state fluorescent materials.