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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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Kaur, A. et al.
Synt. Metals, 126, 283-283 (2002)
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
Pratik Sen et al.
The journal of physical chemistry. B, 109(8), 3319-3323 (2006-07-21)
Solvation dynamics of 4-(dicyanomethylene)-2-methyl-6(p-dimethylaminostyryl) 4H-pyran (DCM) has been studied in a dipalmitoyl-phosphatidylcholine (DPPC) vesicle entrapped in a sodium silicate derived sol-gel glass. Solvation dynamics in DPPC in a sol-gel glass is described by two components of 350 +/- 50 ps
Panchromatic quasi-solid-state squaraine dye sensitized solar cells enhanced by Forster resonance energy transfer of DCM-pyran.
Yun H, et al.
Dyes and Pigments, 113(3), 675-681 (2015)
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)
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