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Merck
CN

747211

Merocyanine dye, HB194

Synonym(s):

2-((Z)-2-((E)-2-(1,1-Dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ylidene)ethylidene)-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 2-[(Z)-2-[(E)-2-(5,6-Dihydro-1,1-dimethyl-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ylidene)ethylidene]-2,3-dihydro-3-oxo-1H-inden-1-ylidene]propanedinitrile

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About This Item

Empirical Formula (Hill Notation):
C27H21N3O
Molecular Weight:
403.48
NACRES:
NA.23
PubChem Substance ID:
329765817
UNSPSC Code:
12352103
MDL number:
MFCD28009149

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InChI

1S/C27H21N3O/c1-27(2)22-11-5-7-17-8-6-14-30(25(17)22)23(27)13-12-21-24(18(15-28)16-29)19-9-3-4-10-20(19)26(21)31/h3-5,7,9-13H,6,8,14H2,1-2H3/b21-12-,23-13+

SMILES string

O=C(C1=C2C=CC=C1)/C(C2=C(C#N)C#N)=C\C=C3C(C)(C)C4=C5C(CCCN5/3)=CC=C4

InChI key

XCFYTQCAMLKFSO-ABLMNQNHSA-N

form

solid

mp

288-290 °C

λmax

~578 nm in dichloromethane

General description

Merocyanine dye, HB194 belongs to the class of absorption materials that are majorly used as donor molecules in organic electronic devices. It has a high absorption coefficient and good polarizing properties, which allow it to be utilized as a photorefractive material.

Application

VAC-processed single high-efficiency Small-BHJ solar cell based on the MC dye
OPV Device Structure: ITO/MoO3/HB194: C60/BPhen/Al
  • JSC = 13.0 mA/cm2
  • VOC = 0.96 V
  • FF = 0.49
  • PCE = 6.1%

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR0846V

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Steinmann; Vera;
Advanced Energy Materials, 1(5), 888-893 (2011)
Direct comparison of highly efficient solution-and vacuum-processed organic solar cells based on merocyanine dyes.
Kronenberg NM, et al.
Advanced Materials, 22(37), 4193-4197 (2010)
Tailored merocyanine dyes for solution-processed BHJ solar cells.
Burckstummer H, et al.
Journal of Materials Chemistry, 20(2), 240-243 (2010)

Articles

Understanding and Successfully Applying Materials for Dye-Sensitized Solar Cells

While dye sensitization as the basis for color photography has been accepted for a very long time,1 attempts to use this principle for the conversion of solar light to electricity generally had resulted only in very low photocurrents, below 100 nA/cm

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