365547-20-2

Basic information

• Product Name: 4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene
• Synonyms: 4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene;4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene;4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene;4,4-Di-2-ethylhexyl-cyclopenta[2,1-b:3,4-b']dithiophene;4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b
• CAS NO: 365547-20-2
• Molecular Formula: C25H38S2
• Molecular Weight: 402.69922
• EINECS: -0
• Mol File: 365547-20-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 490.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.007±0.06 g/cm3(Predicted)
• Refractive Index: 1.5430 to 1.5470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene(365547-20-2)
• EPA Substance Registry System: 4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene(365547-20-2)

Safety Data

• Hazardous Substances Data: 365547-20-2(Hazardous Substances Data)

Usage

General Description

4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene is a chemical compound that belongs to the class of dithiophene, a type of organic compound known for its use in various electronic and optoelectronic applications. It is commonly used as a building block in the synthesis of organic semiconductors and polymers used in organic photovoltaics, organic light-emitting diodes, and organic field-effect transistors. Its unique molecular structure and properties make it suitable for use in the development of high-performance electronic and optoelectronic devices. Additionally, its 2-ethylhexyl substituents contribute to its solubility and processability, making it useful for solution-processable fabrication methods.

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 31936-92-2 1,1-di(thien-3-yl)-methanol 
• 474416-59-6 bis(2-iodothiophen-3-yl)methanol 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 7525-90-8 3-(thiophen-3-ylmethyl)thiophene 
• 18908-66-2 3-bromomethylheptane 
• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 78196-93-7 (4H-cyclopenta<2,1-b:3,4-b'>dithiophene)-4-carboxylic acid 

Downstream Products

• 920515-35-1 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene 
• 365547-21-3 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 1423124-61-1 4,4-bis(2-ethylhexyl)-2H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6(4H)-dione 
• 920504-00-3 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 

Relevant articles and documents

In situ monitoring the thermal degradation of PCPDTBT low band gap polymers with varying alkyl side-chain patterns

The degradation pattern of a series of low band gap PCPDTBT polymers under thermal stress is investigated by in situ UV-vis and FT-IR techniques combined with thermal degradation analysis. Thermogravimetric analysis is used to predetermine the decomposition intervals, revealing that thermolysis occurs in two stages. TG-TD-GC/MS shows that loss of the alkyl side chains predominantly happens within the first temperature regime and degradation of the polymer backbone occurs thereafter. UV-vis spectroscopy is used to monitor the evolution of the optical properties upon heating, reflecting the thermal stability of the conjugated backbone, whereas FT-IR spectroscopy is applied to evaluate the chemical changes under thermal stress, with an emphasis on the polymer periphery. The influence of the side chains and possible defects, dependent on the synthesis protocol applied, on the thermal stability of the final polymers is discussed and is related to the application of said materials in organic photovoltaics.

Influence of different copolymer sequences in low band gap polymers on their performance in organic solar cells

The chemical design of a polymer can be tailored by a random or a block sequence of the comonomers in order to influence the properties of the final material. In this work, two sequences, PCPDTBT and F8BT (F8), were polymerized to form a block or a random copolymer. Differences between the various polymers were examined by exploring the surface topography and charge carrier mobility. A distinct surface texture and a higher charge carrier mobility was found for the block copolymer with respect to the other materials. Solar cells were prepared with polymer:PC71BM blend active layers and the best performance of up to 2% was found for the block copolymer, which was a direct result of the fill factor. Overall, the sequences of different copolymers for solar cell applications were varied and a positive impact on efficiency was found when the block copolymer structure was utilized.

Electron-deficient diketone unit engineering for non-fused ring acceptors enabling over 13% efficiency in organic solar cells

Different from the commonly studied non-fullerene electron acceptors with large fused backbone architecture and tedious synthesis steps, non-fused ring electron acceptors are attractive for organic solar cells (OSC) due to their simple synthesis and comparable device performance. However, it is key to choose appropriate building blocks for constructing non-fused ring electron acceptors to achieve high-performance OSCs. Herein, two simple non-fused ring electron acceptors,TPDC-4FandBTIC-4F, which possess the same terminals and 4H-cyclopenta[1,2-b:5,4-b′]dithiophene unit coupled with different electron-deficient diketone central units, are synthesized.TPDC-4Fwith a thieno[3,4-c]pyrrole-4,6-dione core exhibits a smaller optical bandgap of 1.42 eV, downshifted lowest unoccupied molecular orbital energy levels, higher electron mobility, and enhanced molecular packing order in neat thin films as compared toBTIC-4Fwith a 2,2′-bithiophene-3,3′-dicarboxyimide core. As a result, the OSC based onTPDC-4Fwith stronger molecular packing yielded a high power conversion efficiency (PCE) of 13.35% with aVocof 0.852 V, which is one of the best values ever reported in non-fused ring electron acceptors-based binary OSCs withVocover 0.85 V, and is better than that of OSC based on theBTIC-4Fwith weaker molecular stacking (PCE = 12.04%). This work demonstrates the application of electron-deficient diketone units in efficient non-fused ring electron acceptors and provides molecular design guidance for high-performance OSCs.

Planar quinone structure-containing small molecule organic semiconductor material and preparation and application thereof

The invention relates to a planar quinone structure-containing small molecule organic semiconductor material and preparation and application thereof. The general structural formula of the material isshown in a formula I. The prepared planar quinone structure-based small molecule material has good solubility, can be dissolved in common organic solvents, and organic optoelectronic devices can be prepared through processing of a solution of the small molecule organic semiconductor material; and the small molecule organic semiconductor material has good responses to solar spectra, and thus, can be used as an active layer material of organic solar cells, the migration ability of carriers can be improved due to good planarity of the small molecule organic semiconductor material, and therefore the small molecule organic semiconductor material can also be applied to preparation of active layer materials of organic field-effect transistors.