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790524

Sigma-Aldrich

2-[7-(4-Diphenylaminophenyl)-2,1,3-benzothiadiazol-4-yl]methylenepropanedinitrile

96%

Synonym(s):

2-((7-(4-(Diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile, DPDCPB

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About This Item

Empirical Formula (Hill Notation):
C28H17N5S
CAS Number:
1393343-60-6
Molecular Weight:
455.53
MDL number:
MFCD27978257
UNSPSC Code:
12352103
PubChem Substance ID:
329768220
NACRES:
NA.23

Assay

96%

form

solid

mp

203-207 °C

λmax

549 nm in dichloromethane

semiconductor properties

P-type

SMILES string

N#CC(C#N)=CC1=CC=C(C2=CC=C(N(C3=CC=CC=C3)C4=CC=CC=C4)C=C2)C5=NSN=C15

InChI

1S/C28H17N5S/c29-18-20(19-30)17-22-13-16-26(28-27(22)31-34-32-28)21-11-14-25(15-12-21)33(23-7-3-1-4-8-23)24-9-5-2-6-10-24/h1-17H

InChI key

FWTUEQONZCDFRW-UHFFFAOYSA-N

Application

A vacuum-deposited organic solar cell employing this novel donor-acceptor-acceptor (D-A-A) donor molecule; DPDCPB; combined with the electron acceptor C60/ C70 achieved a record-high power conversion efficiency (PCE) of 5.6%.

Device structure:
MoO3 (30nm) / DPDCPB (7nm) / DPDCPB:C70 (40nm) / C70 (7nm) / BCP (10nm) / Ag (150nm)

Device performance:
  • JSC = 11.45 mA/cm2
  • VOC = 1.0 V
  • FF = 0.5
  • PCE = 5.6%

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Yi-Hong Chen et al.
Journal of the American Chemical Society, 134(33), 13616-13623 (2012-07-27)
Three new tailor-made molecules (DPDCTB, DPDCPB, and DTDCPB) were strategically designed and convergently synthesized as donor materials for small-molecule organic solar cells. These compounds possess a donor-acceptor-acceptor molecular architecture, in which various electron-donating moieties are connected to an electron-withdrawing dicyanovinylene
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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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