1147124-23-9

Basic information

• Product Name: 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo
• Synonyms: 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo;6-Bromo-3-[6-bromo-1-(2-ethylhexyl)-1,2-dihydro-2-oxo-3H-indol-3-ylidene]-1-(2-ethylhexyl)-1,3-dihydro-2H-indol-2-one;6,6'-DibroMo-1,1'-bis(2-ethylhexyl)-[3,3'-biindolinylidene]-2,2'-dione;6,6'-dibromo-N,N'-bis(2-ethylhexyl)-isoindigo
• CAS NO: 1147124-23-9
• Molecular Formula: C₃₂H₄₀Br₂N₂O₂
• Molecular Weight: 644.4802
• EINECS: 200-258-5
• Product Categories: Isoindigo
• Mol File: 1147124-23-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 105-110°C
• Boiling Point: 634.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.338±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.01±0.20(Predicted)
• CAS DataBase Reference: 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo(1147124-23-9)
• EPA Substance Registry System: 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo(1147124-23-9)

Safety Data

• Hazardous Substances Data: 1147124-23-9(Hazardous Substances Data)

Usage

Description

6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo is a chemical compound with a unique molecular structure that features a bromine atom and a 2-ethylhexyl group attached to an isoindigo backbone. 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo is known for its potential applications in the field of organic electronics due to its electron-accepting properties.

Uses

Used in Organic Electronics:
6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo is used as an electron-accepting building block for the preparation of electroactive materials in the field of organic electronics. Its unique molecular structure allows it to contribute to the development of advanced electronic devices with improved performance and functionality.
Used in the Production of Monolayer Sheets:
In the field of materials science, 6,6'-DibroMo-N,N'-(2-ethylhexyl)-isoindigo is utilized in the creation of monolayer sheets. These sheets are characterized by their thin, uniform structure, which can be observed using scanning electron microscopy (SEM). The compound's properties make it suitable for the development of novel materials with potential applications in various industries, such as electronics, energy, and biotechnology.

Upstream product

• 18908-66-2 3-bromomethylheptane 
• 1210390-71-8 6-bromoisoindigo 
• 1147124-21-7 1,1'-dihydro-6,6'-dibromoisoindigo 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 6326-79-0 6-bromoisatin 

Relevant articles and documents

The effect of the length of alkyl side-chains on the molecular aggregation and photovoltaic performance of the isoindigo-based polymers

To investigate the length of the alkyl side-chains on the photovoltaic performance, three isoindigo-based polymers with different-length side chains on the thiophene-benzene-thiophene (TBT) (electron-donating) moiety and isoindigo (electron-withdrawing) moiety have been designed and synthesized, in which the total carbon atom numbers of the side chains in a constitutional repeating unit are completely identical. The results indicate that the polymer with longer branched side chains on the TBT units and shorter linear side chains on the isoindigo units shows stronger interchain interaction and light-harvesting capacity in 1,2-dichlorobenzene solution and thin film, lower band gaps, stronger π?π stacking interaction, more appropriate microphase separation with PC71BM, higher hole mobility and better photovoltaic performance. As a result, the bulk heterojunction (BHJ) device based on PTBTOD-IDB with 2-octyldodecyl on the TBT moiety and n-butyl on the isoindigo moiety exhibits a power conversion efficiency (PCE) of 5.29%, which is almost eight times as high as that of PTBTEH-IDHD with 2-ethylhexyl side chain on TBT moiety and 2-hexyldecyl side chain on isoindigo moiety.

Organic solar cell receptor material and preparation method thereof

The invention provides an isoindigo derivative organic solar cell receptor material and a preparation method thereof. The compound has good heat stability, higher carrier mobility and a higher molar extinction coefficient; organic solar cell devices prepared from the compound have good photoelectric conversion efficiency and a higher fill factor. The structures of isoindigo derivatives are shown in the description, wherein AK is selected from one of a saturated alkyl chain with a carbon atom number of 1-20, an ether chain or a siloxane chain, and X represents H or CF3.

Novel panchromatic absorption material, isoindigo-based A-π-A-π-A small molecule

One A-π-A-π-A small molecule [I(TPTA)2], containing two planar acceptor units, isoindigo, and 2,4,6-triphenyl-1,3,5-triazine (TPTA) with thiophene as bridge, was synthesized by the Suzuki coupling reaction. The obtained molecule exhibits panchromatic absorption between 300 and 720nm with a large half band width up to 350nm in thin solid film. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of [I(TPTA)2] are -5.50 and -3.82 eV. Density functional theory (DFT) calculations indicated that the structure of [I(TPTA)2] is quite planar and that the electron density is mainly delocalized over the central isoindigo and thiophene units.