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736015

Sigma-Aldrich

D149 Dye

98% (HPLC)

Synonym(s):

5-[[4-[4-(2,2-Diphenylethenyl)phenyl]-1,2,3-3a,4,8b-hexahydrocyclopent[b]indol-7-yl]methylene]-2-(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)-4-oxo-3-thiazolidineacetic acid, Indoline dye D149, Purple Dye

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About This Item

Empirical Formula (Hill Notation):
C42H35N3O4S3
CAS Number:
786643-20-7
Molecular Weight:
741.94
UNSPSC Code:
12352103
PubChem Substance ID:
329765075
NACRES:
NA.23

assay

98% (HPLC)

form

solid

mp

284-289 °C

λmax

531 nm

SMILES string

CCN1C(=S)SC(\C1=O)=C2\SC(=C/c3ccc4N(C5CCCC5c4c3)c6ccc(cc6)\C=C(\c7ccccc7)c8ccccc8)\C(=O)N2CC(O)=O

InChI

1S/C42H35N3O4S3/c1-2-43-40(49)38(52-42(43)50)41-44(25-37(46)47)39(48)36(51-41)24-27-18-21-35-33(23-27)31-14-9-15-34(31)45(35)30-19-16-26(17-20-30)22-32(28-10-5-3-6-11-28)29-12-7-4-8-13-29/h3-8,10-13,16-24,31,34H,2,9,14-15,25H2,1H3,(H,46,47)/b36-24-,41-38+

InChI key

OZFUEQNYOBIXTB-SJIUXOFISA-N

General description

D149 Dye is an indoline dye that has an extinction coefficient of 68700 mol-1cm. It has a high conversion efficiency and can be used as a sensitizer.

Application

D149 dye can be used as an organic dye to enhance the absorption of dye sensitized solar cells (DSSCs).
Open-circuit Voltage - Voc(mV) - 708.6
Jsc(mA/cm2) = 14.05
Fill factor − ff − 0.67
Efficiency − η − 6.67

Cell area: 0.25 cm2 (0.5 cm × 0.5 cm)
TiO2 Thickness: 5 μm
FTO glass: AGC Fabritec A11DU80
TiO2: screen printing (Catalysts & Chemicals IND. Co., Ltd.
PST−18NR/400C (4/1 mixture paste)
Electrolyte; 0.1 M LiI; 0.05 M I2; 0.6 M Dimethylpropylimidazolium
Iodide; 0.05 M t-Butylpyridine in 3-Methoxypropionitrile
Light source: AM1.5 1sun
Counter Electrode: Pt/Cr spatter glass
Dye adsorption: 30 °C/ in 3 hr. (t-BuOH/acetonitrile soln.)
Photosensitive Red-Violet dye having excellent photoelectric conversion efficiency as a metal-free dye.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

546127

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High-efficiency organic-dye-sensitized solar cells controlled by nanocrystalline-TiO2 electrode thickness
Ito S, et al.
Advanced Materials, 18(9), 1202-1205 (2006)
Tamotsu Horiuchi et al.
Journal of the American Chemical Society, 126(39), 12218-12219 (2004-09-30)
We now report metal-free organic dyes having a new type of indoline structure, which exhibits high efficiencies in dye-sensitized solar cells. The solar energy to current conversion efficiencies with the new indoline dye was 6.51%. Under the same conditions, the
Characterization of solid-state dye-sensitized solar cells utilizing high absorption coefficient metal-free organic dyes
Howie WH, et al.
Journal of the American Chemical Society, 130(4), 1367-1375 (2008)
Organic dye-sensitized ionic liquid based solar cells: remarkable enhancement in performance through molecular design of indoline sensitizers
Kuang D, et al.
Advanced Materials, 120(10), 1949-1953 (2008)
Masanori Miyashita et al.
Journal of the American Chemical Society, 130(52), 17874-17881 (2008-12-11)
Electron diffusion coefficient, lifetime, and density in the TiO(2) electrode of dye-sensitized TiO(2) solar cells (DSCs) employing I(-)/I(3)(-) redox couples were measured with eight different metal-free organic dyes and three Ru complex dyes. At matched electron density, all DSCs using
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