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

97%

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Synonym(s):
3,6-Di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, DPP
Empirical Formula (Hill Notation):
C14H8N2O2S2
CAS Number:
Molecular Weight:
300.36
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

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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David Rais et al.
ChemPlusChem, 85(12), 2689-2703 (2020-12-18)
The singlet fission (SF) process discovered in bis(thienyl)diketopyrrolopyrroles (TDPPs) can boost their potential for photovoltaics (PV). The crystal structures of TDPP analogs carrying n-hexyl, n-butyl, or 2-(adamant-1-yl)ethyl substituents are similar, but contain increasingly slipped stacked neighbor molecules. The observed SF
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)
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)
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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