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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)

Synonym(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

Empirical Formula (Hill Notation):
C28H19N5S2
CAS Number:
1335150-09-8
Molecular Weight:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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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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)
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)
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.

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