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777293

Sigma-Aldrich

2-{[7-(5-N,N-Ditolylaminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

99% (HPLC)

Sinónimos:

2-[[7-[5-[Bis(4-methylphenyl)amino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]methylene]propanedinitrile, DTDCTB

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About This Item

Fórmula empírica (notación de Hill):
C28H19N5S2
Número de CAS:
1335150-09-8
Peso molecular:
489.61
MDL number:
MFCD25976535
UNSPSC Code:
12352103
PubChem Substance ID:
329767897
NACRES:
NA.23

assay

99% (HPLC)

form

powder

mp

230-235 °C

transition temp

Tm 233 °C

λmax

662-664 nm in dichloromethane

SMILES string

CC(C=C1)=CC=C1N(C2=CC=C(C)C=C2)C3=CC=C(C4=CC=C(C=C(C#N)C#N)C5=NSN=C54)S3

InChI

1S/C28H19N5S2/c1-18-3-8-22(9-4-18)33(23-10-5-19(2)6-11-23)26-14-13-25(34-26)24-12-7-21(15-20(16-29)17-30)27-28(24)32-35-31-27/h3-15H,1-2H3

InChI key

BCJCBXQJAANTJL-UHFFFAOYSA-N

General description

2-{[7-(5-N,N-Ditolylaminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile (DTDCTB) is a conducting polymer that can be used as a donor molecule. It is majorly used in the development of organic electronics.
Device structure:
MoO3 (30nm) / DTDCTB (7nm) / DTDCTB:C60/C70 (40nm) / C60/C70 (7nm) / BCP (10nm) / Ag

Device performance:
  • JSC = 14.68 mA/cm2
  • VOC = 0.8 V
  • FF = 0.5
  • PCE = 5.81%

Application

A vacuum-deposited organic solar cell employing this novel donor-acceptor-acceptor (D-A-A) donor molecule; DTDCTB; combined with the electron acceptor C60/ C70 achieved a record-high power conversion efficiency (PCE) of 5.81%.
DTDCTB is a π-conjugating polymer that can be used in the fabrication of organic solar cells (OSCs) and organic photovoltaic cells (OPVs).

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Highly efficient bifacial transparent organic solar cells with power conversion efficiency greater than 3% and transparency of 50%.
Lin H, et al.
Organic Electronics, 13(9), 1722-1728 (2012)
The role of the charge-transfer states in the ultrafast excitonic dynamics of the DTDCTB dimers embedded in a crystal environment.
Jiang S, et al.
Chemical Physics, 515, 603-613 (2018)
An effective bilayer cathode buffer for highly efficient small molecule organic solar cells.
Lin H, et al.
Organic Electronics, 13(10), 1925-1929 (2012)
Deposition growth and morphologies of C60 on DTDCTB surfaces: An atomistic insight into the integrated impact of surface stability, landscape, and molecular orientation.
Han G, et al.
Advanced Materials Interfaces, 2(17), 1500329-1500329 (2015)
Li-Yen Lin et al.
Journal of the American Chemical Society, 133(40), 15822-15825 (2011-09-13)
A novel donor-acceptor-acceptor (D-A-A) donor molecule, DTDCTB, in which an electron-donating ditolylaminothienyl moiety and an electron-withdrawing dicyanovinylene moiety are bridged by another electron-accepting 2,1,3-benzothiadiazole block, has been synthesized and characterized. A vacuum-deposited organic solar cell employing DTDCTB combined with the

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Development of Small Molecule Donors for Solution-Processed Organic Solar Cells

Solution-processed organic photovoltaic devices (OPVs) have emerged as a promising clean energy generating technology due to their ease of fabrication, potential to enable low-cost manufacturing via printing or coating techniques, and ability to be incorporated onto light weight, flexible substrates.

Development of Small Molecule Donors for Solution-Processed Organic Solar Cells

Solution-processed organic photovoltaic devices (OPVs) have emerged as a promising clean energy generating technology due to their ease of fabrication, potential to enable low-cost manufacturing via printing or coating techniques, and ability to be incorporated onto light weight, flexible substrates.

Development of Small Molecule Donors for Solution-Processed Organic Solar Cells

Solution-processed organic photovoltaic devices (OPVs) have emerged as a promising clean energy generating technology due to their ease of fabrication, potential to enable low-cost manufacturing via printing or coating techniques, and ability to be incorporated onto light weight, flexible substrates.

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