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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

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

Certificats d'analyse (COA)

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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)
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)
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
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.
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Journal of Luminescence, 158(7), 441-446 (2015)
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