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

CAS Number 850583-75-4

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers


Product Code B961-5g
Price £210 ex. VAT

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

One of the most frequently used organic building blocks for the synthesis of oligomers and polymers having promising semiconducting properties in application of highly efficient OFETs, OLEDs and OPVs.


Specifications | MSDS | Literature and Reviews


2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione, CAS number 850583-75-4, contains a diketopyrrolopyrrole (DPP) core with 2-thienyl groups at 3,6-positions. Diketopyrrolopyrroles (DPPs) are by far one of the most frequently used organic building blocks for the synthesis of oligomers and polymers having promising semiconducting properties in application of OFETs, OLEDs and OPVs. Alkyl groups can be introduced to both amines to increase solubility and film morphology of the target molecules. Further bromination of the thienyl groups can lead to brominated DPP derivatives which are convenient intermediates for C-C bond formations for structural modification of DPP cores.

One of the well-known features of the DPP-based materials is their relatively high oxidation potential due to the fact that DPP core is electron deficient. Higher oxidation potential leads to high-energy charge separated states when combined with fullerenes or non-fullerene acceptors and correspondingly high open voltages when used in solar cells. DPP-based materials can also extend their absorption to near infrared (NIR) absorption to find potential applications in photodetectors and photothermal therapy.

DPP-based materials have also been known for their great charge mobility in OFET devices due to the intermolecular π-π interactions with their fused highly planar DPP core units. OTFT devices fabricated with high molecular weights of DPP-DTT have exhibited very high mobility up to 10.5 cm2 V−1 s−1 and on/off ratio ≥106, with exceptional device shelf-life and operational stabilities. Highest hole mobility 26.2 cm2 V−1 s−1 was achieved by incorporating an ionic additive tetramethylammonium iodide (NMe4I) with DPP-DTT at 1:30 molar ratio.

Chemical Structure

6,6′-2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione chemical structure, CAS 850583-75-4
2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) chemical structure, CAS 850583-75-4

General Information


CAS Number 850583-75-4
Chemical Formula C14H8N2O2S2
Full Name 2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione
Molecular Weight 300.36 g/mol
Synonyms

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

DPP 3,6-Di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Classification / Family Diketopyrrolopyrroles, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Product Details


Purity >95% (by 1H NMR)
Melting Point N/A
Appearance Dark red/brown powder/crystals

MSDS Documentation


2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione MSDS2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione MSDS Sheet

Pricing


Batch Quantity Price
B961 5 g £210
B961 10 g £340
B961 25 g £680

Literature and Reviews


  1. A design strategy for high mobility stretchable polymer semiconductors, J. Mun et al., Nat. Commun., 12, 3572 (2021); DOI: 0.1038/s41467-021-23798-2.
  2. Diketopyrrolopyrrole Based Organic Semiconductor Materials for Field-Effect Transistors, X Zou et al., Front. Chem., 9, 671294 (2021); DOI: 10.3389/fchem.2021.671294.
  3. Remarkable enhancement of charge carrier mobility of conjugated polymer field-effect transistors upon incorporating an ionic additive, H. Luo et al, Sci. Adv., 2, e1600076 (2016); DOI: 10.1126/sciadv.1600076.
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