389-58-2

Basic information

• Product Name: 3,4-Dithia-7H-cyclopenta[a]pentalene
• Synonyms: 3,4-Dithia-7H-cyclopenta[a]pentalene;4H-Cyclopenta[2,1-b:3,4-b']dithiophene;3,4-b']dithiophene;4H-Cyclopenta[2,1-b;DTCPP;4H-cyclopenta[1,2-b:5,4-b']bisthiophene;4H-cyclopenta[1,2-b:5,4-b']dithiophene;4H-Cyclopenta[2,1-b:3,4-b
• CAS NO: 389-58-2
• Molecular Formula: C₉H₆S₂
• Molecular Weight: 178.27
• EINECS: 1592732-453-0
• Product Categories: DTC
• Mol File: 389-58-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 71.0 to 75.0 °C
• Boiling Point: 307.8 °C at 760 mmHg
• Flash Point: 103.1 °C
• Appearance: /
• Density: 1.400
• Storage Temp.: 0-10°C
• Solubility: soluble in Toluene
• CAS DataBase Reference: 3,4-Dithia-7H-cyclopenta[a]pentalene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dithia-7H-cyclopenta[a]pentalene(389-58-2)
• EPA Substance Registry System: 3,4-Dithia-7H-cyclopenta[a]pentalene(389-58-2)

Safety Data

• Hazardous Substances Data: 389-58-2(Hazardous Substances Data)

Usage

Description

4H-cyclopenta[2,1-b:3,4-b′]dithiophene, also known as CPDT, a rigid coplanar structure favouring π?π intermolecular interactions with good electron-donating properties, has been one of the most attractive building blocks for organic field effect transistors and organic electronics. The five-member ring in the middle also offer the function to have side-chain manipulation to enhance solubility in solutions for device fabrications, morphology and polymer processing. One of the intensively studied polymer for organic electrons, PCPDTBT, with the alternating CPDT and 2,1,3- benzothiadiazole (BT) units, has demonstrated device performance of PCE over 6% [5]

Uses

4H-Cyclopenta[2,1-b:3,4-b'']dithiophene is useful in the synthesis of donor-acceptor copolymers.

Upstream product

• 78196-93-7 (4H-cyclopenta<2,1-b:3,4-b'>dithiophene)-4-carboxylic acid 
• 17965-52-5 2,2'-dibromo-3,3'-dithienylmethane 
• 25796-77-4 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one 
• 498-62-4 3-thiophene carboxaldehyde 
• 31936-92-2 1,1-di(thien-3-yl)-methanol 
• 7525-90-8 3-(thiophen-3-ylmethyl)thiophene 
• 40032-67-5 (+/-)-2-hydroxy-1,2-di(thiophen-3-yl)ethanone 
• 78196-92-6 (3,3'-Dithienyl)glycolic Acid 
• 7333-08-6 3,3'-Thenil 
• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 1352312-45-8 bis(2-iodothien-3-yl)methane 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 474416-59-6 bis(2-iodothiophen-3-yl)methanol 

Downstream Products

• 153312-87-9 4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 153312-86-8 4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene 
• 737792-43-7 4,4-bis-{3-[4-tert-butyl-2-(5-tert-butyl-2-methoxy-benzyl)-phenoxy]-propyl}-4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 365547-20-2 4,4-bis(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 
• 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 
• 1351757-80-6 C₃₂H₂₇NOS₂ 
• 1351757-84-0 C₃₅H₂₈N₂O₂S₂ 
• 1351757-82-8 C₃₈H₃₁NO₃S₃ 
• 1351757-85-1 C₄₁H₃₂N₂O₄S₃ 
• 1315276-46-0 6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 1221821-39-1 6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 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

One-pot cross-coupling of diborylmethane for the synthesis of dithienylmethane derivatives

The one-pot palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of a diborylmethane with bromothiophene derivatives realized the synthesis of various dithienylmethane derivatives. Cyclopentadithiophenes, which are promising compounds in material science, can be obtained in good yields. The in situ generation of an unstable thienylmethylboronate is a key step for the present reaction. Georg Thieme Verlag Stuttgart New York.

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification relates to a compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1. The abovementioned compound can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment of the present invention can improve the efficiency, the low driving voltage and/or the lifetime characteristics in the organic light emitting device.COPYRIGHT KIPO 2018

Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes

Over the past 20 years, ruthenium(II)-based dyes have played a pivotal role in turning dye-sensitized solar cells (DSCs) into a mature technology for the third generation of photovoltaics. However, the classic I3-/I- redox couple limits the performance and application of this technique. Simply replacing the iodine-based redox couple by new types like cobalt(3+/2+) complexes was not successful because of the poor compatibility between the ruthenium(II) sensitizer and the cobalt redox species. To address this problem and achieve higher power conversion efficiencies (PCEs), we introduce here six new cyclometalated ruthenium(II)-based dyes developed through ligand engineering. We tested DSCs employing these ruthenium(II) complexes and achieved PCEs of up to 9.4% using cobalt(3+/2+)-based electrolytes, which is the record efficiency to date featuring a ruthenium-based dye. In view of the complicated liquid DSC system, the disagreement found between different characterizations enlightens us about the importance of the sensitizer loading on TiO2, which is a subtle but equally important factor in the electronic properties of the sensitizers.