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Sigma-Aldrich

Coumarin 6

≥99%

Synonym(s):

3-(2-Benzothiazolyl)-7-(diethylamino)coumarin, 3-(2-Benzothiazolyl)-N,N-diethylumbelliferylamine

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About This Item

Empirical Formula (Hill Notation):
C20H18N2O2S
CAS Number:
38215-36-0
Molecular Weight:
350.43
Beilstein/REAXYS Number:
1085798
EC Number:
253-830-2
MDL number:
MFCD00041869
UNSPSC Code:
12352103
PubChem Substance ID:
329758042
NACRES:
NA.23

assay

≥99%

form

solid

mp

208-210 °C (lit.)

λmax

443 nm

fluorescence

λem 494 nm in THF
λem 505 nm in ethanol (Lasing peak 534 nm, lasing range 515 - 558 nm (DMSO), pump source XeCl (308 nm))

orbital energy

HOMO 5.4 eV 
LUMO 2.7 eV 

OLED device performance

ITO/Alq3:Coumarin 6/Mg:Ag

  • Color: green
  • Max. EQE: 2.5 %

SMILES string

CCN(CC)c1ccc2C=C(C(=O)Oc2c1)c3nc4ccccc4s3

InChI

1S/C20H18N2O2S/c1-3-22(4-2)14-10-9-13-11-15(20(23)24-17(13)12-14)19-21-16-7-5-6-8-18(16)25-19/h5-12H,3-4H2,1-2H3

InChI key

VBVAVBCYMYWNOU-UHFFFAOYSA-N

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General description

Coumarin 6 as fluorescence lifetime standards in fluorescence spectroscopy was reported to be the most stable for performing lifetime experiments.

Application

It may be used to calibrate fluorescence lifetime imaging microscopy system.
Material used as Green Dopant
Laser dye

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Seokjoon Lee et al.
Bioorganic & medicinal chemistry letters, 16(17), 4596-4599 (2006-06-24)
A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular
Monitoring protein interactions in living cells with fluorescence lifetime imaging microscopy
Sun Y, et al.
Methods in Enzymology null
Xin Guan et al.
Drug delivery, 23(9), 3307-3318 (2016-04-14)
Utilization of quercetin (QT) in clinics is limited by its instability and poor solubility. To overcome these disadvantages, we prepared QT as QT-loaded PLGA-TPGS nanoparticles (QPTN) and examined its properties and therapeutic efficacy for liver cancer. QT-loaded PLGA nanoparticles (QPN)
Testing fluorescence lifetime standards using two-photon excitation and time-domain instrumentation: rhodamine B, coumarin 6 and lucifer yellow.
Kristoffersen AS,et al.
Journal of Fluorescence null
Deborah D Soto-Ortega et al.
Bioorganic & medicinal chemistry, 19(8), 2596-2602 (2011-04-05)
Aggregation of the amyloid-β protein (Aβ) plays a pathogenic role in the progression of Alzheimer's disease, and small molecules that attenuate Aβ aggregation have been identified toward a therapeutic strategy that targets the disease's underlying cause. Compounds containing aromatic structures
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