51325-91-8

Basic information

• Product Name: 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN
• Synonyms: (2-(p-(dimethylamino)styryl)-6-methyl-4h-pyran-4-ylidene)malononitrile;initrile;lidene]-;propanedinitrile,(2-(2-(4-(dimethylamino)phenyl)ethenyl)-6-methyl-4h-pyran-4;propanedinitrile,[2-[2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-4h-pyran-4-y;DCM;4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN;4-(DICYANOMETHYLENE)-2-METHYL-6-(P-DIMETHYLAMINOSTYRYL)-4H-PYRAN
• CAS NO: 51325-91-8
• Molecular Formula: C₁₉H₁₇N₃O
• Molecular Weight: 303.36
• EINECS: 257-137-6
• Product Categories: electronic;Electroluminescence;Functional Materials;oled materials
• Mol File: 51325-91-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 215-220 °C(lit.)
• Boiling Point: 444.29°C (rough estimate)
• Flash Point: 110 °F
• Appearance: Dark red/Powder or Crystalline Needles
• Density: 1.239
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5900 (estimate)
• Storage Temp.: Flammables area
• PKA: 5.46±0.24(Predicted)
• Merck: 14,2838
• CAS DataBase Reference: 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN(51325-91-8)
• EPA Substance Registry System: 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN(51325-91-8)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20-36/37/38-20/21/22-10
• Safety Statements: 16-26-36-7/9-36/37
• RIDADR: UN 3175 4.1/PG 2
• WGK Germany: 3
• RTECS: OO3746100
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 51325-91-8(Hazardous Substances Data)

Usage

Chemical Properties

red/brown crystals

Uses

DCM can be used as a laser dye to enhance the emission of distributed feedback (DFB) device by F?rster resonance energy transfer (FRET). It may be used as a capping layer that allows the conversion of blue to red colored emission in organic light emitting diodes (OLED). DCM may also find potential applications in the enhancement of energy transfer of different devices like metal organic frameworks (MOFs), dye sensitized solar cells (DSSCs) and polarity sensors.

General Description

4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM) is a red laser dye that consists of dicyanomethylene as an electron acceptor and dimethylaniline group as an electron donor. It has a π-conjugated 4H-pyran-4-ylidiene which bridges both the acceptor/donor groups. It can be used as a dopant and also in organic solid state lasers.

InChI:InChI=1/C19H17N3O/c1-14-10-16(17(12-20)13-21)11-19(23-14)9-6-15-4-7-18(8-5-15)22(2)3/h4-11H,1-3H3/b9-6+

Upstream product

• 28286-88-6 4-dicyanomethylene-2,6-dimethyl-4H-pyran 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 124-40-3 dimethyl amine 

Relevant articles and documents

A luminescence molecular switch via modulation of PET and ICT processes in DCM system

A novel versatile dicyanomethylene-4H-pyran (DCM) based derivative bearing ferrocenyl group (DCM-N-Fc) is designed as modulator to construct “off-on” logic operation. The optical properties of DCM-N-Fc are characterized by absorption and steady-state fluorescence technique, showing that the fluorescence from DCM chromophore via intramolecular charge transfer (ICT) is strongly quenched by photoinduced electron transfer (PET) process from ferrocene moiety. In contrast with the references (DCM-N and DCM-Fc), the fluorescence of DCM-N-Fc can be triggered by oxidizing ferrocenyl unit either chemically or electrochemically, exhibiting a characteristic emission modulation at around 610 nm with an electrofluorochromic behavior. Furthermore, the free energy and the fluorescence lifetime in the PET path verify the thermodynamic feasibility. Cyclic voltammetry, absorption spectroscopy, time-resolved fluorescence as well as DFT calculation have been used to elaborate the manipulation via both PET and ICT processes.

A fluorescent compound and its use on medicine

The invention relates to a fluorescent compound with A beta plaque affinity and a composition which contains the derivative, namely the fluorescent compound. The fluorescent compound is as shown in a general formula (I), wherein a substituent group in the general formula (I) is as shown in the specification. The invention also relates to a preparation method of the fluorescent compound and an application of the fluorescent compound in a method for developing A beta plaques.