4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

Base Information

• Chemical Name: 4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene
• CAS No.: 153312-86-8
• Molecular Formula: C21H30S2
• Molecular Weight: 346.59
• Mol file: 153312-86-8.mol

Synonyms:4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

Chemical Property of 4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

Chemical Property:

• Boiling Point: 447.4±25.0 °C(Predicted)
• PSA: 56.48000
• Density: 1.041±0.06 g/cm3(Predicted)
• LogP: 8.01690
• Storage Temp.: 2-8°C

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

There total 11 articles about 4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene 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: 95.0%

4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2) + 1-bromo-hexane (111-25-1) → 4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene (153312-86-8)

Guidance literature:

With potassium iodide; potassium hydroxide; In dimethyl sulfoxide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.200903562

Reference yield: 82.0%

4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2) + 1-Chlorohexane (544-10-5) → 4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene (153312-86-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; at 75 ℃; for 4h;

DOI:10.1039/c4ra08119f DOI:10.1039/c4ra08119f

Reference yield:

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b’]dithiophene (153312-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / potassium hydroxide; hydrazine hydrate / ethane-1,2-diol / 8 h / 180 °C

2: potassium hydroxide; potassium iodide / dimethylsulfoxide

With potassium hydroxide; hydrazine hydrate; potassium iodide; In ethylene glycol; dimethyl sulfoxide; 1: Wolff-Kischner reduction;

DOI:10.1021/ma0258354

upstream raw materials:

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

1-bromo-hexane

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

3-thiophene carboxaldehyde

Downstream raw materials:

6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde

2-cyano-3-{6-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-yl}acrylic acid

4-(4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)-N,N-bis(4-(hexyloxy)phenyl)aniline

6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde

Refernces

• 1、 Coppo, Paolo,Cupertino, Domenico C.,Yeates, Stephen G.,Turner, Michael L.. "Synthetic routes to solution-processable polycyclopentadithiophenes". . p. 2705 - 2711. Retrieved 2003.
• 2、 Marco, A. Beln,De Baroja, Natalia Martnez,Franco, Santiago,Garn, Javier,Orduna, Jess,Villacampa, Beln,Revuelto, Alejandro,Andreu, Raquel. "Dithienopyrrole as a rigid alternative to the bithiophene π relay in chromophores with second-order nonlinear optical properties". . p. 188 - 197. Retrieved 2015.
• 3、 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.