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.
2,5-Dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione 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 of the 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 has 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.
|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|
|Purity||>95% (by 1H NMR)|
|Appearance||Dark red/brown powder/crystals|
Literature and Reviews
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.
- Diketopyrrolopyrrole Based Organic Semiconductor Materials for Field-Effect Transistors, X Zou et al., Front. Chem., 9, 671294 (2021); DOI: 10.3389/fchem.2021.671294.
- 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.
- Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics, S. Qu et al., Chem. Commun., 48, 3039–3051 (2012); DOI: 10.1039/c2cc17886a.
- A Simple Structure Conjugated Polymer for High Mobility Organic Thin Film Transistors Processed from Nonchlorinated Solvent, Z. Wang et al., Adv. Sci., 6, 1902412 (2019); DOI: 10.1002/advs.201902412.
- Developments of Diketopyrrolopyrrole-Dye-Based Organic Semiconductors for a Wide Range of Applications in Electronics, Q. Liu, et al., Adv. Mater., 32 (4), 1903882 (2020); DOI: 10.1002/adma.201903882.
- Diketopyrrolopyrrole: A Versatile Building Block for Organic Photovoltaic Materials, D. Chandran et al., Macromol. Res., 21 (3), 272-283 (2013); DOI 10.1007/s13233-013-1141-3.
- A stable solution-processed polymer semiconductor with record high-mobility for printed transistors, J. Li et al., Nature Scientific Reports, 2, 754, DOI: 10.1038/srep00754 (2012).
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