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Sigma-Aldrich

2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione

97%

Synonym(s):

3,6-Di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, DPP

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About This Item

Empirical Formula (Hill Notation):
C14H8N2O2S2
CAS Number:
850583-75-4
Molecular Weight:
300.36
MDL number:
MFCD20257907
UNSPSC Code:
12352103
PubChem Substance ID:
329767335
NACRES:
NA.23

Quality Level

100

assay

97%

form

solid

SMILES string

O=C1NC(c2cccs2)=C3C(=O)NC(c4cccs4)=C13

InChI

1S/C14H8N2O2S2/c17-13-9-10(12(16-13)8-4-2-6-20-8)14(18)15-11(9)7-3-1-5-19-7/h1-6H,(H,15,18)(H,16,17)

InChI key

YIUHGBNJJRTMIE-UHFFFAOYSA-N

Related Categories

General description

2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione is a diketopyrrolopyrrole (DPP) based copolymer and are used widely in thin-film transistors and solar cell devices. This aromatic polymer has electron withdrawing groups and hence is very useful for the synthesis of narrow band gap donor-acceptor polymers which are used as active semiconductors for organic electronics. They give rise to high power conversion efficiency (PCE) in Organic Photovoltaic (OPV) Cells.

Application

Used in the synthesis of donor-acceptor polymers which are used in polymer field-effect transistors and bulk heterojunction solar cells.

Features and Benefits

Diketopyrrolopyrrole is planar and can accept hydrogen bonds/other electrostatic interactions which results in copolymers that have pi-pi stacking.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ9520
MKCH6918
MKCF0931
MKCC5312
MKCB9650

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Influence of Side-Chain on Structural Order and Photophysical Properties in Thiophene Based Diketopyrrolopyrroles: A Systematic Study.
Naik, M. A., Venkatramaiah, N., Kanimozhi, C., & Patil, S.
The Journal of Physical Chemistry C, 116(50), 26128-26137 (2012)
Synthesis and characterization of phenanthrocarbazole-diketopyrrolopyrrole copolymer for high-performance field-effect transistors
Chen, H., Guo, Y., Sun, X., Gao, D., Liu, Y., & Yu, G.
Journal of Polymer Science Part A: Polymer Chemistry, 51(10), 2208-2215 (2013)
Hugo Bronstein et al.
Journal of the American Chemical Society, 133(10), 3272-3275 (2011-02-22)
We report the synthesis and polymerization of a novel thieno[3,2-b]thiophene-diketopyrrolopyrrole-based monomer. Copolymerization with thiophene afforded a polymer with a maximum hole mobility of 1.95 cm(2) V(-1) s(-1), which is the highest mobility from a polymer-based OFET reported to date. Bulk-heterojunction

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NTz Building Blocks for Organic Semiconductors

The field of organic electronics has emerged as the next-generation technology potentially enabling ultra-thin, large-area, and/or flexible devices, consisting of organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs), and organic photovoltaics (OPVs).

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