927896-66-0

Basic information

• Product Name: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
• Synonyms: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
• CAS NO: 927896-66-0
• Molecular Formula: C22H12N2O2S4
• Molecular Weight: 464.6
• EINECS: -0
• Mol File: 927896-66-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione(927896-66-0)
• EPA Substance Registry System: 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione(927896-66-0)

Safety Data

• Hazardous Substances Data: 927896-66-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione is utilized as a key component in the development of organic solar cells due to its ability to enhance light absorption and charge transport, thereby improving the efficiency of solar energy conversion.
Additionally, it is used as a semiconductor material in the fabrication of organic field-effect transistors, where its electronic properties contribute to the performance and functionality of these transistors.
Furthermore, due to its potential applications in various electronic devices, 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione is considered a promising candidate for future technological advancements in the field of organic electronics.

Upstream product

• 1509901-31-8 di-tert-butyl-3,6-di(2,2′-bithiophen-5-yl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5-(1H,4H)-dicarboxylate 

Relevant articles and documents

Influence of solubilizing group removal rate on the morphology and crystallinity of a diketopyrrolopyrrole-based compound

Thermally cleavable solubilizing groups have been introduced on a π-conjugated core, which can be cleaved and volatilized via heat treatment directly after the thin film fabrication. The X-ray and atomic force microscopic investigations of 3,6-di(2,2′-bithiophen-5-yl)pyrrolo[3,4-c] pyrrole-1,4-(2H,5H)-dione (DPP-4T) synthesized from its precursor (di-tert-butyl-3,6-di(2,2′-bithiophen-5-yl)-1,4-dioxopyrrolo[3,4-c] pyrrole-2,5-(1H,4H)-dicarboxylate) through thermal conversion reveals that the solubilizing group removal rate plays a crucial role on the ultimate grain size and crystallinity of the final compound (DPP-4T). This means that, when the heating rate is decreased from 50 to 0.1 °C/min, the crystallinity of DPP-4T powder decreases from 49% to 34%, and the grain size of DPP-4T film reduces from 976 to 344 nm. The crystallite size of the films can be further reduced to 185 nm by decarboxylating the films isothermally at 120 °C. The Fourier transform infrared spectra reveals that the reduction of crystallinity with the heating rate could be attributed to the trapping of gaseous byproducts inside the lattice, during the decarboxylation of the solubilizing group. The increment in intermolecular N-H···O=C hydrogen bond length together with the trapped gaseous byproducts results in a blue shift in the UV-vis absorption spectra while decreasing the heating rate as well as the isothermal decarboxylation temperature.

PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE

The present invention relates to compounds of the formula (I) wherein the substituents are as defined in claim 1, and their use as organic semiconductor in organic devices, like diodes, organic field effect transistors and/or a solar cells. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).