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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)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C28H19N5S2
Numéro CAS:
1335150-09-8
Poids moléculaire :
489.61
Numéro MDL:
MFCD25976535
Code UNSPSC :
12352103
ID de substance PubChem :
329767897
Nomenclature NACRES :
NA.23

Pureté

99% (HPLC)

Forme

powder

Pf

230-235 °C

Température de transition

Tm 233 °C

λmax

662-664 nm in dichloromethane

Chaîne SMILES 

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

Clé InChI

BCJCBXQJAANTJL-UHFFFAOYSA-N

Description générale

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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
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)
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

Articles

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.

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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