Sexithiophene

Base Information

• Chemical Name: Sexithiophene
• CAS No.: 88493-55-4
• Molecular Formula: C24H14 S6
• Molecular Weight: 494.771
• Hs Code.: 29349990
• European Community (EC) Number: 626-183-2
• DSSTox Substance ID: DTXSID90462870
• Nikkaji Number: J602.557I
• Wikidata: Q72507451
• Mol file: 88493-55-4.mol

Synonyms:sexithiophene

Chemical Property of Sexithiophene

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 4.23E-14mmHg at 25°C
• Melting Point: 290 ºC (dec.)(lit.)
• Boiling Point: 608.5°C at 760 mmHg
• Flash Point: 245.5°C
• PSA: 169.44000
• Density: 1.402
• LogP: 10.39060
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 493.94197749
• Heavy Atom Count: 30
• Complexity: 536

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sexithiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC=C(S2)C3=CC=C(S3)C4=CC=C(S4)C5=CC=C(S5)C6=CC=CS6
• Uses: Sexithiophene is an organic semiconductor/transistor.

Technology Process of Sexithiophene

There total 12 articles about Sexithiophene 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: 84.0%

5-bromo-2,2':5',2''-terthiophene (94581-95-0) → sexithiophene (88493-55-4)

Guidance literature:

With potassium fluoride; bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In methanol; toluene; at 70 ℃; for 0.166667h; microwave irradiation;

DOI:10.1021/jo035723q

Reference yield: 81.0%

2,2'-Bithiophene (492-97-7) → quaterthiophene (5632-29-1) + 2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octithiophene (113728-71-5) + sexithiophene (88493-55-4)

Guidance literature:

2,2'-Bithiophene; With mercury(II) trifluoroacetate; In benzene; at 0 ℃; for 0.25h;

With triethylamine; palladium dichloride; In benzene; at 0 ℃; for 0.25h; Further stages.;

DOI:10.1021/jo025838e

Reference yield: 70.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) → quaterthiophene (5632-29-1) + 2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octithiophene (113728-71-5) + sexithiophene (88493-55-4)

Guidance literature:

thiophene; With mercury(II) trifluoroacetate; In benzene; at 0 ℃; for 0.25h;

With triethylamine; palladium dichloride; In benzene; at 0 ℃; for 0.25h; Further stages.;

DOI:10.1021/jo025838e

upstream raw materials:

2-Iodothiophene

5,5'-diiodo-2,2-bithiophene

5-iodo-2,2':5'2-terthiophene

5,5’’-diiodo-2,2’:5’,2“-terthiophene

Downstream raw materials:

α-sexithiophene-5-carboxaldehyde

Refernces

• 1、 Gimenez, Elena,Carilla, Josep,Fajari, Lluis,Aleman, Carlos,Julia, Luis. "Thallium(III) Trifluoroacetate-Trifluoroacetic Acid in the Chemistry of Polythiophenes. 1. Polymers from 2,2'-Bithiophene and 2,2',5',2''-Terthiophene. Mechanistic Aspects". . p. 4630 - 4636. Retrieved 1994.
• 2、 Buzhansky, Ludmila,Feit, Ben-Ami. "A novel approach to a one-pot synthesis of unsubstituted oligo(α-thiophenes)". . p. 7523 - 7525. Retrieved 2007/10/03.