Merck
CN
All Photos(2)

Documents

410497

Sigma-Aldrich

4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran

Dye content 98 %

Sign Into View Organizational & Contract Pricing
All Photos(2)
Synonym(s):
DCM
Empirical Formula (Hill Notation):
C19H17N3O
CAS Number:
51325-91-8
Molecular Weight:
303.36
EC Number:
257-137-6
MDL number:
MFCD00051341
PubChem Substance ID:
24865530
NACRES:
NA.23

form

solid

composition

Dye content, 98%

mp

215-220 °C (lit.)

λmax

468 nm

OLED Device Performance

ITO/Alq3:DCM/Alq3/Mg:Ag

  • Color: red
  • Max. EQE: 1.3 %

ITO/TPD/Alq3:DCM (10%)/Alq3/Mg:Ag
  • Color: red
  • Max. Luminance: 150 Cd/m2

SMILES string

CN(C)c1ccc(\C=C\C2=CC(\C=C(C)O2)=C(\C#N)C#N)cc1

InChI

1S/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+

InChI key

YLYPIBBGWLKELC-RMKNXTFCSA-N

Related Categories

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.

Application

DCM can be used as a laser dye to enhance the emission of distributed feedback (DFB) device by FÖrster 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.

Features and Benefits

Voltage-tunable multicolor emission with enhanced luminance (~1000 cd/m2) was observed using varying amounts of DCM dye in a polymer light-emitting diode (PLED).

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

109.4 °F - closed cup

Flash Point(C)

43 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Tunable two-color luminescence and host-guest energy transfer of fluorescent chromophores encapsulated in metal-organic frameworks.
Yan D, et al.
Scientific reports, 4(3), 4337-4337 (2014)
Yang Zhao et al.
Physical chemistry chemical physics : PCCP, 11(48), 11538-11545 (2009-12-22)
The equilibrium geometries, electronic structures, one-photon absorption (OPA) and two-photon absorption (TPA) properties of starburst 4-(dicyanomethylene)-2-methyl-6-[p-(dimethylamino)styryl]-4H-pyran (DCM) derivatives have been studied by using density functional theory (DFT) and Zerner's intermediate neglect of differential overlap (ZINDO) program. Results showed that increasing
Arnab Halder et al.
Langmuir : the ACS journal of surfaces and colloids, 20(3), 653-657 (2005-03-19)
Solvation dynamics of 4-(dicyanomethylidene)-2-[p-(dimethylamino)styryl]-6-methyl-4H-pyran (DCM) is studied in a polypeptide-surfactant aggregate consisting of gelatin and sodium dodecyl sulfate (SDS) in potassium dihydrogen phosphate (KP) buffer. The average solvation time (tauS) in gelatin-SDS aggregate at 45 degrees C is found to
Aaron J Van Tassle et al.
The journal of physical chemistry. B, 110(38), 18989-18995 (2006-09-22)
Time resolved visible pump, infrared probe transient absorption measurements of the solutes 4-dicyanomethylene-2-methyl-6-(p-(dimethylamino)styryl)-4H-pyran (DCM) and its isotopomer DCM-d6 are employed to probe the dynamics of charge transfer state formation in dimethyl sulfoxide (DMSO) and acetonitrile (MeCN). We observe a two
Marco Leonetti et al.
Optics letters, 34(24), 3764-3766 (2009-12-18)
We present a detailed study of the gain length in an active medium obtained by doping of DNA strands with 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran dye molecules. The superior thermal stability of the composite and its low quenching permit one to obtain an optical
View All Related Papers

Articles

Fluorescence Quenching Microscopy: Imaging Two-Dimensional Materials

Developed in the last several years, fluorescence quenching microscopy (FQM) has enabled rapid, inexpensive, and high-fidelity visualization of two-dimensional (2D) materials such as graphene-based sheets and MoS2.

Graphene in Biotechnology

Graphene is the building block for carbon nanomaterials with different dimensionalities.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service