3,4-Dithia-7H-cyclopenta[a]pentalene

Base Information

• Chemical Name: 3,4-Dithia-7H-cyclopenta[a]pentalene
• CAS No.: 389-58-2
• Molecular Formula: C9H6S2
• Molecular Weight: 178.279
• Hs Code.: 2934999090
• Mol file: 389-58-2.mol

Synonyms:CPDT;

Chemical Property of 3,4-Dithia-7H-cyclopenta[a]pentalene

Chemical Property:

• Melting Point: 71.0 to 75.0 °C
• Boiling Point: 307.8 °C at 760 mmHg
• Flash Point: 103.1 °C
• PSA: 56.48000
• Density: 1.4 g/cm³
• LogP: 3.38080
• Storage Temp.: 0-10°C
• Solubility.: soluble in Toluene

Purity/Quality:

99.0% ^*data from raw suppliers

4H-Cyclopenta[2,1-b:3,4-b'']dithiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 3,4-Dithia-7H-cyclopenta[a]pentalene

There total 17 articles about 3,4-Dithia-7H-cyclopenta[a]pentalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.3%

(4H-cyclopenta<2,1-b:3,4-b'>dithiophene)-4-carboxylic acid (78196-93-7) → 4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2)

Guidance literature:

With quinoline; copper; at 237 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/pola.25933

Reference yield: 89.0%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2)

Guidance literature:

With hydrazine hydrate; potassium hydroxide; In ethylene glycol; at 180 ℃;

DOI:10.1055/s-0033-1341278

Reference yield: 61.0%

C10H6O3S2 → 4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide;

DOI:10.5012/bkcs.2010.31.04.1064

upstream raw materials:

(4H-cyclopenta<2,1-b:3,4-b'>dithiophene)-4-carboxylic acid

2,2'-dibromo-3,3'-dithienylmethane

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

3-thiophene carboxaldehyde

Downstream raw materials:

4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene

2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

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

Refernces

• 1、 Benincori, Tiziana,Appoloni, Giulio,Mussini, Patricia Romana,Arnaboldi, Serena,Cirilli, Roberto,Quartapelle Procopio, Elsa,Panigati, Monica,Abbate, Sergio,Mazzeo, Giuseppe,Longhi, Giovanna. "Searching for Models Exhibiting High Circularly Polarized Luminescence: Electroactive Inherently Chiral Oligothiophenes". . p. 11082 - 11093. Retrieved 2018/08/01.
• 2、 Rakstys, Kasparas,Paek, Sanghyun,Gao, Peng,Gratia, Paul,Marszalek, Tomasz,Grancini, Giulia,Cho, Kyung Taek,Genevicius, Kristijonas,Jankauskas, Vygintas,Pisula, Wojciech,Nazeeruddin, Mohammad Khaja. "Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE". supporting information. p. 7811 - 7815. Retrieved 2017/07/13.