5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene

Base Information

• Chemical Name: 5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene
• CAS No.: 151271-43-1
• Molecular Formula: C₃₆H₃₈S₆
• Molecular Weight: 663.094
• DSSTox Substance ID: DTXSID70569831
• Nikkaji Number: J657.759H
• Wikidata: Q82457067
• Mol file: 151271-43-1.mol

Synonyms:151271-43-1;5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene;5 5''''-DIHEXYL-2 2';2-hexyl-5-[5-[5-[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene;SCHEMBL2032335;DTXSID70569831;MFCD06411295;| inverted exclamation mark,| -DH6T;5,5-Dihexyl-2,2:5,2:5,2:5;CS-0433629;1~5~,6~5~-Dihexyl-1~2~,2~2~:2~5~,3~2~:3~5~,4~2~:4~5~,5~2~:5~5~,6~2~-sexithiophene;5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene, electron donor for OPV devices

Chemical Property of 5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene

Chemical Property:

• Melting Point: 280 °C (dec.)(lit.)
• Boiling Point: 700.9±55.0 °C(Predicted)
• PSA: 169.44000
• Density: 1.204±0.06 g/cm3(Predicted)
• LogP: 14.63620
• Solubility.: chlorobenzene: solublesoluble
• XLogP3: 14.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 662.12977825
• Heavy Atom Count: 42
• Complexity: 729

Purity/Quality:

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

5,5′′′′′-Dihexyl-2,2′:5′,2′′:5′′,2′′′:5′′′,2′′′′:5′′′′,2′′′′′-sexithiophene electron donor for OPV devices ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1=CC=C(S1)C2=CC=C(S2)C3=CC=C(S3)C4=CC=C(S4)C5=CC=C(S5)C6=CC=C(S6)CCCCCC
• Uses: DH6T can be used as a p-type donor molecule for the fabrication of organic electronic devices such as organic field effect transistors (OFETs), thin film transistors (TFTs) and organic solar cells (OSCs).

Technology Process of 5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene

There total 4 articles about 5,5'''''-Dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-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: 61.0%

2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene (151271-42-0) → α,ω-Dihexylsexithiophene (151271-43-1)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.833333h;

With copper dichloride; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 17h;

Reference yield:

2,2'-Bithiophene (492-97-7) → α,ω-Dihexylsexithiophene (151271-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide, acetic acid / CHCl₃

2: 1.) n-BuLi, tetramethylenediamine, 2.) zinc chloride, 3.) tetrakis(triphenylphosphino)palladium

3: 1.) n-BuLi, tetramethylenediamine, 2.) CuCl₂ / 1.) THF, -70 deg C, 30 min, 2.) THF, from -60 deg C to RT, 18 h

With N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; copper dichloride; zinc(II) chloride; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In chloroform;

DOI:10.1021/ja00072a026

Reference yield:

2-hexylthiophene (18794-77-9) → α,ω-Dihexylsexithiophene (151271-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, tetramethylenediamine, 2.) zinc chloride, 3.) tetrakis(triphenylphosphino)palladium

2: 1.) n-BuLi, tetramethylenediamine, 2.) CuCl₂ / 1.) THF, -70 deg C, 30 min, 2.) THF, from -60 deg C to RT, 18 h

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; copper dichloride; zinc(II) chloride; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾;

DOI:10.1021/ja00072a026

upstream raw materials:

2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene

2-hexylthiophene

2,2'-Bithiophene

5-bromo(2,2'-bithiophene)

Refernces

• 1、 Garnier, Francis,Yassar, Abderrahim,Hajlaoui, Ryad,Horowitz, Gilles,Deloffre, Fran?oise,Servet, Bernard,Ries, Simone,Alnot, Patrick. "Molecular engineering of organic semiconductors: Design of self-assembly properties in conjugated thiophene oligomers". . p. 8716 - 8721. Retrieved 2007/10/02.