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410497

Sigma-Aldrich

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

Dye content 98 %

Synonym(s):

DCM

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250 MG
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1 G
€168.00

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250 MG
€51.40
1 G
€168.00

About This Item

Empirical Formula (Hill Notation):
C19H17N3O
CAS Number:
51325-91-8
Molecular Weight:
303.36
EC Number:
257-137-6
MDL number:
MFCD00051341
UNSPSC Code:
12352103
PubChem Substance ID:
24865530
NACRES:
NA.23

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form

solid

Quality Level

200

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

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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.[1][2]

Application

DCM can be used as a laser dye to enhance the emission of distributed feedback (DFB) device by FÖrster resonance energy transfer (FRET).[3] It may be used as a capping layer that allows the conversion of blue to red colored emission in organic light emitting diodes (OLED).[4] DCM may also find potential applications in the enhancement of energy transfer of different devices like metal organic frameworks (MOFs),[5] dye sensitized solar cells (DSSCs)[6] and polarity sensors.[7]

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).[8]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H228,H315,H319,H332,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM8496
MKBX0728V
MKBP5232V
79396PJV
79396PJ

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Ashim Pramanik et al.
Journal of colloid and interface science, 565, 326-336 (2020-01-25)
The development of white light-emitting LED (WLED) is now one of the important demands of present society due to its energy saving feature. However, in this work, an ingenious strategy has been employed to develop Forster resonance energy transfer (FRET)
Solid state solvation effect and reduced amplified spontaneous emission threshold value of glass forming DCM derivative in PMMA films.
Vembris A, et al.
Journal of Luminescence, 158(7), 441-446 (2015)
Tunable organic distributed feedback dye laser device excited through Forster mechanism.
Tsutsumi N and Hinode T
Applied Physics B: Lasers and Optics, 123(3), 93-93 (2017)
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)
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
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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