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410497

Sigma-Aldrich

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

Dye content 98 %

Synonyme(s) :

DCM

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About This Item

Formule empirique (notation de Hill):
C19H17N3O
Numéro CAS:
51325-91-8
Poids moléculaire :
303.36
Numéro CE :
257-137-6
Numéro MDL:
MFCD00051341
Code UNSPSC :
12352103
ID de substance PubChem :
24865530
Nomenclature NACRES :
NA.23

Forme

solid

Niveau de qualité

200

Composition

Dye content, 98%

Pf

215-220 °C (lit.)

λmax

468 nm

Performance des dispositifs OLED

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

Chaîne SMILES 

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+

Clé InChI

YLYPIBBGWLKELC-RMKNXTFCSA-N

Description générale

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.

Caractéristiques et avantages

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).

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H228,H315,H319,H332,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

4.1B - Flammable solid hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

109.4 °F - closed cup

Point d'éclair (°C)

43 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
SHBM8496
MKBX0728V
MKBP5232V
79396PJV
79396PJ

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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
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
Luminous composite ultrathin films of the DCM dye assembled with layered double hydroxides and its fluorescence solvatochromism properties for polarity sensors.
Qin Y, et al.
Journal of Material Chemistry C, 3(20), 5246-5252 (2015)
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
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)
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