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Sigma-Aldrich

3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-hexyldecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione

98%

Synonym(s):

Pyrrolo[3,4-c]pyrrole-1,4-dione,3,6-bis(5-bromo-2-thienyl)-2-5-bis(2-hexyldecyl)-2,5-dihydro-

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About This Item

Empirical Formula (Hill Notation):
C46H70Br2N2O2S2
CAS Number:
1000623-98-2
Molecular Weight:
907.00
MDL number:
MFCD28098664
UNSPSC Code:
12352103
PubChem Substance ID:
329767826
NACRES:
NA.23

assay

98%

form

solid

mp

110-115 °C

SMILES string

O=C1N(CC(CCCCCC)CCCCCCCC)C(C2=CC=C(Br)S2)=C3C1=C(C4=CC=C(Br)S4)N(CC(CCCCCC)CCCCCCCC)C3=O

InChI

1S/C46H70Br2N2O2S2/c1-5-9-13-17-19-23-27-35(25-21-15-11-7-3)33-49-43(37-29-31-39(47)53-37)41-42(45(49)51)44(38-30-32-40(48)54-38)50(46(41)52)34-36(26-22-16-12-8-4)28-24-20-18-14-10-6-2/h29-32,35-36H,5-28,33-34H2,1-4H3

InChI key

MNALLGNMYJQSHP-UHFFFAOYSA-N

General description

3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-hexyldecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (DDP-Br2) belongs to the series of diketopyrrolopyrrole (DPP) based materials which show hole or ambipolar transport behavior with mobilities of charge carriers in the range of 0.1-1 cm2V-1 s-1. It has an electron deficient core that forms a low LUMO energy level which facilitates better air-stability for n-type organic semiconductors.

Application

DDP-Br2 can be used in the fabrication of a variety of opto-electronic devices such as organic field effect transistors (OFETs), perovskite based solar cells, non-fullerene organic solar cells.
Novel acceptors utilized in low band gap polymer cells and showed optical bandgaps ranging from 1.81 to 1.94 eV and intense absorption bands that cover a wide range from 300 to 700 nm

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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Journal of Materials Chemistry, 21, 1600-1606 (2011)
Diketopyrrolopyrrole-containing quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel organic field-effect transistors
Qiao Y, et al.
Journal of the American Chemical Society, 134(9), 4084-4087 (2012)
Hole-transporting diketopyrrolopyrrole-thiophene polymers and their additive-free application for a perovskite-type solar cell with an efficiency of 16.3%
Maruo H, et al.
Polymer Journal, 51(1), 91-91 (2019)
Journal of Materials Chemistry, 22, 2120-2128 (2012)
A Novel BODIPY-Based Low-Band-Gap Small-Molecule Acceptor for Efficient Non-fullerene Polymer Solar Cells
Liu W, et al.
Chin. J. Chem., 35(12), 1813-1823 (2017)
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