1214906-01-0

Basic information

• Product Name: 3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• Synonyms: K0116
• CAS NO: 1214906-01-0
• Molecular Formula: C₂₆H₃₀Br₂N₂O₂S₂
• Molecular Weight: 626.4644
• Mol File: 1214906-01-0.mol

Chemical Properties

• CAS DataBase Reference: 3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1214906-01-0)
• EPA Substance Registry System: 3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1214906-01-0)

Safety Data

• Hazardous Substances Data: 1214906-01-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione is used as a key component in the development of organic photovoltaic devices due to its ability to enhance the efficiency of solar energy conversion. The electron-rich nature of the compound contributes to improved charge transport and light absorption properties, which are crucial for the performance of these devices.
Additionally, it is utilized in the fabrication of organic field-effect transistors, where its high electron mobility is advantageous for creating devices with faster response times and better electrical performance. 3,6-Bis(5-broMothiophen-2-yl)-2,5-dihexylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione's structural design allows for fine-tuning of the transistor's electronic characteristics, making it a versatile material for various electronic applications within this industry.

Upstream product

• 852435-01-9 2,5-N,N'-bis(hexyl)-3,6-bis(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione 
• 111-25-1 1-bromo-hexane 

Relevant articles and documents

Synthesis of diketopyrrolopyrrole containing copolymers: A study of their optical and photovoltaic properties

The diketopyrrolopyrrole-based copolymers PDPP-BBT and TDPP-BBT were synthesized and used as a donor for bulk heterojunction photovoltaic devices. The photophysical properties of these polymers showed absorption in the range 500-600 nm with a maximum peak around 563 nm, while TDPP-BBT showed broadband absorption in the range 620 - 800 nm with a peak around 656 nm. The power conversion efficiencies (PCE) of the polymer solar cells based on these copolymers and [6,6]-phenyl C61 butyric acid methyl ester (PCBM) were 0.68% (as cast PDPP-BBT:PCBM), 1.51% (annealed PDPP-BBT:PCBM), 1.57% (as cast TDPPBBT:PCBM), and 2.78% (annealed TDPP-BBT:PCBM), under illumination of AM 1.5 (100 mW/cm2). The higher PCE for TDPP-BBT-based polymer solar cells has been attributed to the low band gap of this copolymer as compared to PDPP-BBT, which increases the numbers of photogenerated excitons and corresponding photocurrent of the device. These results indicate that PDPP-BBT and TDPP-BBT act as excellent electron donors for bulk heterojunction devices. ? 2010 American Chemical Society.

Diketopyrrolopyrrole compound with terminal group containing bi[n]alkynyl and application of diketopyrrolopyrrole compound

The invention relates to a diketopyrrolopyrrole compound with a terminal group containing bi[n]alkynyl and application of the diketopyrrolopyrrole compound. The diketopyrrolopyrrole compound is shown as a general molecular formula in the description, wherein R1 refers to straight-chain paraffin or branched paraffin, R2 refers to H atom, trimethylsilyl, straight-chain paraffin or branched paraffin, and n is an integer not less than 1. The diketopyrrolopyrrole compound with the terminal group containing the bi[n]alkynyl can be widely applied to organic light-emitting diodes, field-effect transistors and solar cells.

Preparation method of diketopyrrolopyrrole compound with bi[n]alkynyl-containing terminal group

The invention relates to a preparation method of a diketopyrrolopyrrole compound with a bi[n]alkynyl-containing terminal group. 3, 6-bis(thiophene-2-yl)pyrrolo[3, 4-C]pyrrole-1, 4-dione (DPP) and a bi[n]alkynyl group-containing micromolecule undergo a reaction to produce the diketopyrrolopyrrole compound and n is an integer greater than or equal to 1. The preparation method comprises that a terminal alkyne-DPP derivative and 1-alkyne undergo a Glaser coupling reaction to produce a desired product of which n is 1 or 2, or comprises that a soluble dibromo-DPP derivative and bi[n]alkyne undergo a Cadiot-Chodkiewicz coupling reaction to produce a high-yield desired product of which n is greater than or equal to 2. The diketopyrrolopyrrole compound can be widely used in fields of organic light-emitting diodes, field-effect tubes and solar cells.

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: What did we find out?

The primary role of substituted side chains in organic semiconductors is to increase their solubility in common organic solvents. In the recent past, many literature reports have suggested that the side chains play a critical role in molecular packing and strongly impact the charge transport properties of conjugated polymers. In this work, we have investigated the influence of side-chains on the charge transport behavior of a novel class of diketopyrrolopyrrole (DPP) based alternating copolymers. To investigate the role of side-chains, we prepared four diketopyrrolopyrrole-diketopyrrolopyrrole (DPP-DPP) conjugated polymers with varied side-chains and carried out a systematic study of thin film microstructure and charge transport properties in polymer thin-film transistors (PTFTs). Combining results obtained from grazing incidence X-ray diffraction (GIXD) and charge transport properties in PTFTs, we conclude side-chains have a strong influence on molecular packing, thin film microstructure, and the charge carrier mobility of DPP-DPP copolymers. However, the influence of side-chains on optical properties was moderate. The preferential "edge-on" packing and dominant n-channel behavior with exceptionally high field-effect electron mobility values of >1 cm2 V-1 s-1 were observed by incorporating hydrophilic (triethylene glycol) and hydrophobic side-chains of alternate DPP units. In contrast, moderate electron and hole mobilities were observed by incorporation of branched hydrophobic side-chains. This work clearly demonstrates that the subtle balance between hydrophobicity and hydrophilicity induced by side-chains is a powerful strategy to alter the molecular packing and improve the ambipolar charge transport properties in DPP-DPP based conjugated polymers. Theoretical analysis supports the conclusion that the side-chains influence polymer properties through morphology changes, as there is no effect on the electronic properties in the gas phase. The exceptional electron mobility is at least partially a result of the strong intramolecular conjugation of the donor and acceptor as evidenced by the unusually wide conduction band of the polymer. the Partner Organisations 2014.