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

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

Uses

1. Used in Laser Applications:
DCM is used as a laser dye to enhance the emission of distributed feedback (DFB) devices through F?rster resonance energy transfer (FRET). Its application in this context is due to its ability to improve the efficiency and performance of laser systems.
2. Used in Organic Light Emitting Diodes (OLED):
DCM serves as a capping layer in OLEDs, enabling the conversion of blue to red-colored emission. This application takes advantage of DCM's red laser dye properties to achieve desired color outputs in display technologies.
3. Used in Energy Transfer Enhancement:
DCM may find potential applications in enhancing the energy transfer of various devices, such as metal-organic frameworks (MOFs), dye-sensitized solar cells (DSSCs), and polarity sensors. Its use in these applications is due to its ability to improve the efficiency of energy transfer processes in these technologies.
4. Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, DCM's unique chemical structure and properties may also make it a candidate for pharmaceutical research, particularly in the development of new drugs or drug delivery systems. Further investigation would be required to explore this potential application.

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 
• 1122-91-4 4-bromo-benzaldehyde 
• 124-40-3 dimethyl amine 
• 100-10-7 4-dimethylamino-benzaldehyde 

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.

Transition metal-catalyzed C–N cross-coupling reaction of bromine-substituted pyranilidene derivatives: synthesis, characterization, and optical properties study of pyran-based chromophores

Abstract: In this work, the C–N cross-coupling reaction between bromine-substituted pyranilidene derivatives, and a variety of secondary amines was studied in the presence of transition metal catalysts. The CuI/l-proline, Pd(OAC)2/PPh3, and MnCl2.6H2O/l-proline were chosen as catalyst/ligand systems. The copper-catalyzed Ullmann amination reaction in the presence of l-proline as auxiliary ligand shows the best yield. The structure of pyran-based chromophores was confirmed using FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. Additionally, the linear optical properties of final compounds were investigated using UV–Vis and fluorescent spectroscopy. The large stokes shifts for final compounds show the capability of using these compounds in optical applications. Graphic abstract: [Figure not available: see fulltext.].

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.

Ion-Responsive Fluorescent Compounds, 2. Cation-Steered Intramolecular Charge Transfer in a Crowned Merocyanine

The dimethylamine group of DCM (4-dicyanomethylene-2-methyl-6--4H-pyran), a well-known merocyanine often used as a laser dye, has been replaced by a macrocycle (monoaza-15-crown-5) which acts also as an electron donating substituent.The resulting fluoroionophore (DCM-crown) has almost identical photophysical properties as DCM, but upon complexation by alkaline-earth-metal-cations, it undergoes drastic changes in absorption spectrum (hypsochromic shift and hypochromic effect) and fluorescence quantum yield (quenching), whereas the emission spectrum is only slightly blue-shifted and the fluorescence lifetime is almost unchanged.These effects which strongly depend on the charge density of the cation can be interpreted in terms of cation-steered reduction of the efficiency of tranfer from a nonemissive locally excited state to an emissive relaxed intramolecular charge-transfer state (RICT).