154717-19-8

Basic information

• Product Name: 2,2':5',2''-Terthiophene, 3',3'',4-trihexyl-
• CAS NO: 154717-19-8
• Molecular Formula: C30H44S3
• Molecular Weight: 500.877
• Mol File: 154717-19-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,2':5',2''-Terthiophene, 3',3'',4-trihexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2':5',2''-Terthiophene, 3',3'',4-trihexyl-(154717-19-8)
• EPA Substance Registry System: 2,2':5',2''-Terthiophene, 3',3'',4-trihexyl-(154717-19-8)

Safety Data

• Hazardous Substances Data: 154717-19-8(Hazardous Substances Data)

Usage

Description

2,2':5',2''-Terthiophene, 3',3'',4-trihexylis a chemical compound that features a terthiophene core with three hexyl chains attached to specific positions on the molecule. This heterocyclic compound, which contains sulfur, is widely recognized for its role in the synthesis of organic semiconductors, particularly for electronic devices. The incorporation of hexyl chains significantly improves the solubility and processability of the compound, which is advantageous for its application in various electronic components.

Uses

Used in Organic Semiconductors:
2,2':5',2''-Terthiophene, 3',3'',4-trihexylis utilized as a key component in the development of organic semiconductors due to its electronic properties and structural stability. Its presence in these semiconductors contributes to the overall performance and efficiency of electronic devices.
Used in Thin Film Transistors:
In the industry of thin film transistors, 2,2':5',2''-Terthiophene, 3',3'',4-trihexylis employed as a semiconductor material. Its enhanced solubility and processability make it an ideal candidate for creating thin films that are essential in transistor fabrication.
Used in Solar Cells:
2,2':5',2''-Terthiophene, 3',3'',4-trihexylis also used in solar cell technology as a component of organic photovoltaics. Its ability to absorb light and convert it into electricity makes it a valuable material in the advancement of solar energy applications.
Used in Optoelectronics:
2,2':5',2''-Terthiophene, 3',3'',4-trihexylfinds application in the field of optoelectronics, where its unique molecular structure and chemical properties make it suitable for the development of advanced materials used in light-emitting diodes, photodetectors, and other optoelectronic devices.
Overall, 2,2':5',2''-Terthiophene, 3',3'',4-trihexylis a versatile compound with a wide range of applications in the electronics industry, particularly in the development of organic semiconductors and optoelectronic devices. Its unique properties make it a valuable building block for future advancements in these fields.

Upstream product

• 69249-61-2 3-hexyl-2-bromothiophene 
• 1428332-09-5 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene 
• 135926-93-1 3,4'-dihexyl-2,2'-bithiophene 

Downstream Products

• 161116-88-7 5-(5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene-2-yl)-3-hexylthiophene 

Relevant articles and documents

'Donor-free' oligo(3-hexylthiophene) dyes for efficient dye-sensitized solar cells

The common trend in designing dyes for use in DSSCs with iodide-based electrolyte is based on a donor-π spacer-acceptor (D-π-A) architecture. Here, we report two 'donor-free' cyanoacrylic end-functionalized oligo(3-hexylthiophene) dyes (5T and 6T). Despite having no donor group, both dyes show reversible first oxidation process. Both 5T and 6T have n-hexyl alkyl chains to retard aggregation at different positions as well as different numbers of thiophene moieties. However, the dyes showed similar absorption properties and redox potentials. The DSSCs based on these dyes give power conversion efficiencies of more than 7%, although a significant difference in the VOC and FF has been observed. Using electrochemical impedance spectroscopy, this is attributed to the presence of more trap states when 6T attaches to TiO2 and modifies the surface, mainly affecting the fill factor. Overall, these dyes introduce a new and effective design concept for liquid-electrolyte DSSC sensitisers.

Concise synthesis of well-defined linear and branched oligothiophenes with nickel-catalyzed regiocontrolled cross-coupling of 3-substituted thiophenes by catalytically generated magnesium amide

The synthesis of linear and branched oligothiophenes of well-defined structures is performed with regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling of the thus formed metalated species with a bromothiophene. The reaction of 3-hexylthiophene with EtMgCl and 2,2,6,6-tetramethylpiperidine (TMP-H, 10 mol %) induces the metalation selectively at the 5-position by use of the catalytically generated hindered magnesium amide (TMPMgCl) and the subsequent reaction of a 2-halo-3- hexylthiophene (bromide or chloride) in the presence of a nickel catalyst affords a head-to-tail (HT)-type dimer. By repeating the same sequence, the linear oligothiophene up to a 4-mer is synthesized in good yield. The reaction of 3-hexylthiophene with 2,3-dibromothiophene also takes place to afford a branched oligothiophene 3-mer in quantitative yield. The obtained 3-mer is also metalated at the sterically less-hindered position in a regioselective manner furnishing a 7-mer in >99 % yield after a further coupling reaction with 2,3-dibromothiophene. These dendrimers react with several multifunctionalized organic electrophiles, leading to a variety of branched oligothiophenes. Copyright

Synthesis of well-defined head-to-tail-type oligothiophenes by regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling reaction

Iterative growth of thiophene oligomers by single-step extensions has been realized by regioselective metalation of 3-substituted thiophenes with the Knochel-Hauser base (TMPMgCl·LiCl) and coupling with bromothiophene using a nickel catalyst. Treatment of 3-hexylthiophene with TMPMgCl·LiCl induces metalation at the 5-position selectively. Subsequent addition of 2-bromo-3-hexylthiophene and a nickel catalyst leads to the corresponding bithiophene. The obtained bithiophene is converted to the terthiophene and then to the quaterthiophene by repeating the similar protocol. A concise synthesis of MK-1 and MK-2, which are organic dye molecules bearing an oligothiophene moiety that are used in photovoltaic cells, has been achieved.