135926-93-1

Basic information

• Product Name: 3,4'-Dihexyl-2,2'-bithiophene
• Synonyms: 3,4'-Dihexyl-2,2'-bithiophene
• CAS NO: 135926-93-1
• Molecular Formula: C₂₀H₃₀S₂
• Molecular Weight: 334.5822
• Mol File: 135926-93-1.mol

Chemical Properties

• Boiling Point: 165°C/0.02mmHg
• Flash Point: 160.6 °C
• Appearance: /
• Density: 1.009 g/cm³
• Refractive Index: 1.5510-1.5550
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 3,4'-Dihexyl-2,2'-bithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4'-Dihexyl-2,2'-bithiophene(135926-93-1)
• EPA Substance Registry System: 3,4'-Dihexyl-2,2'-bithiophene(135926-93-1)

Safety Data

• Hazardous Substances Data: 135926-93-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronic Devices:
3,4'-Dihexyl-2,2'-bithiophene is used as a semiconductor material in organic field-effect transistors (OFETs) for its high electron mobility and stability. Its incorporation in OFETs enhances the performance and efficiency of these devices, enabling their use in flexible electronics and other applications.
Used in Organic Photovoltaic Cells:
3,4'-Dihexyl-2,2'-bithiophene is utilized as an active layer material in organic photovoltaic (OPV) cells due to its high electron mobility and stability. Its presence in the active layer improves the power conversion efficiency and overall performance of OPV cells, contributing to the development of more efficient and sustainable solar energy solutions.
Used in Solution-Processing Methods:
The long alkyl chains of 3,4'-Dihexyl-2,2'-bithiophene contribute to its solubility in organic solvents, making it suitable for solution-processing methods in the fabrication of organic electronic devices. This property allows for the easy and cost-effective production of thin films and other components, facilitating the large-scale manufacturing of advanced electronic and optoelectronic devices.

Upstream product

• 69249-61-2 3-hexyl-2-bromothiophene 
• 154717-21-2 5’-bromo-3,4’-dihexyl-2,2’-bithiophene 
• 124561-55-3 3-Hexyl-2-iodothiophene 
• 748763-44-2 (4-hexylthiophen-2-yl)boronic acid 
• 1693-86-3 3-hexylthiophene 
• 618887-45-9 tert-butyl-[4-(n-hexyl)thiophen-2-yl]dimethylsilane 
• 618887-46-0 2-[5-(tert-butyldimethylsilanyl)]-[3-(n-hexyl)thiophen-2-yl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 833483-79-7 3',4-dihexyl-5'-iodo-2,2'-bithiophene-5-carboxylic acid benzyl ester 
• 278617-45-1 3',4-dihexyl-2,2'-bithiophene-5-boronic acid propane-1,3-diyl ester 
• 944083-68-5 [4,3'-di-(n-hexyl)-[2,2']bithiophenyl-5-yl]-{2-[4-(2-ethoxyethoxy)phenyl]ethyl}di-para-tolylgermane 
• 438587-18-9 {2-[4-(2-ethoxyethoxy)phenyl]ethyl}-(4-hexylthiophen-2-yl)dimethylgermane 
• 691006-35-6 {2-[4-(2-ethoxyethoxy)phenyl]ethyl}diethyl-[4-(n-hexyl)thiophen-2-yl]germane 
• 164991-12-2 [3-(n-hexyl)thiophen-2-yl]trimethylsilane 
• 691006-33-4 tert-butyl-[3-(n-hexyl)thiophen-2-yl]dimethylsilane 

Downstream Products

• 154717-19-8 5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene 
• 1432475-92-7 4-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]-N,N-diphenylbenzenamine 
• 1432475-93-8 4-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]phenylmorpholine 
• 1037440-21-3 2-cyano-3-[5’’’-(9-ethyl-9H-carbazol-3-yl)-3’,3’’,3’’’,4-tetrahexyl(2,2’:5’,2’’:5’’,2’’’-quaterthiophene)-5-yl]-2-propenoic acid 

Relevant articles and documents

Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

Solid-phase synthesis of isomerically pure head-to-tail-coupled (HT) oligo(3-hexylthiophene)s on chloromethylated polystyrene resin has been developed. Using novel sequences of iodination and Suzuki cross-coupling reaction, a series up to a dodecamer has been synthesized in high yield and purity. Removal of the conjugated oligomers from solid support as methyl esters, saponification and decarboxylation to the HT-coupled oligo(3-alkylthiophene)s could be effectively achieved. The Royal Society of Chemistry 2000.

Synthesis of EDOT -containing polythiophenes and their properties in relation to the composition ratio of EDOT

Polythiophenes composed of 3,4-ethylenedioxythiophene (EDOT) and 3-hexylthiophene with different composition ratios of EDOT in the repeat unit of the polymer backbone are synthesized by polycondensation reactions. The optical and electrochemical properties of the polymers are compared with those of poly(3,4-ethylenedioxythiophene) and poly(3-hexylthiophene), and they are found to be well correlated with the EDOT composition ratio. In addition, the charge transport properties of the polymer films, measured using the in situ conductivity technique, are discussed in terms of the EDOT composition ratio, regioregularity, and the doping level.

A versatile and efficient strategy to discrete conjugated oligomers

An efficient and scalable strategy to prepare libraries of discrete conjugated oligomers (D = 1.0) using the combination of controlled polymerization and automated flash chromatography is reported. From this two-step process, a series of discrete conjugated materials from dimers to tetradecamers could be isolated in high yield with excellent structural control. Facile and scalable access to monodisperse libraries of different conjugated oligomers opens pathways to designer mixtures with precise composition and monomer sequence, allowing exquisite control over their physical, optical, and electronic properties.

A method of manufacturing an organic dye MK-2 (by machine translation)

PROBLEM TO BE SOLVED: To provide a method for producing an organic coloring matter MK-2 in a short period of time and in a good yield.SOLUTION: The method for producing an organic coloring matter MK-2 comprises: a first step of coupling 3-hexylthiophene in the presence fo an iodine catalyst and an activator to synthesize a thiophene dimer having two thiophene molecules bonded (H-T bithiophene); a second step of halogenating a 5-position of the resultant H-T bithiophene; a third step of substituting halogen at a 5-position of the resultant halogenated H-T bithiophene with a 9-ethylcarbazolyl group; a fourth step of halogenating a 5'-position of the resultant 9-ethylcarbazolyl H-T bithiophene; a fifth step of bonding H-T bithiophene to the resultant halogenated body to form a thiophene tetramer; a sixth step of folmylating a thiophene terminal of the resultant thiophene tetramer; and a seventh step of reacting the resultant formylated body with a cyanoacetic acid to produce the MK-2.

'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.

Solution processed bulk heterojunction solar cells based on A-D-A small molecules with a dihydroindoloindole (DINI) central donor and different acceptor end groups

Four acceptor-donor-acceptor (A-D-A) small molecules with dihydroindoloindole (DINI) as the central donor unit and different acceptor end groups such as dicyanovinylene (DCV), indenedione (IND), cyanoacrylate (CA) and rhodanine (Rho) linked through bithiophene as the π-linker, DINI-DCV, DINI-IND, DINI-CA and DINI-Rho, were designed and synthesized for the application as donor materials along with PC71BM as an acceptor for solution processed organic bulk heterojunction solar cells. The effect of acceptor end groups on the photovoltaic performance was investigated. The organic solar cells (OSCs) based on as cast DINI-IND showed the highest power conversion efficiency of 3.04%, as cast DINI-CA showed the lowest PCE of 1.63% and the other two exhibit a PCE in between them. These results showed that acceptor end groups affect the overall performance of the cells. The PCE of OSCs has been further improved up to 7.04% and 6.16% employing two-step annealing (TSA) treated DIN-IND:PC71BM (1:2) and DIN-CN:PC71BM (1:2), respectively. The enhancement in the PCE of OSCs with TSA treated active layers is attributed to the better nanophase morphology, the increase in the crystalline nature and light harvesting efficiency and more balanced charge transport and charge collection probability.

Conjugated polymers with repeated sequences of group 16 heterocycles synthesized through catalyst-transfer polycondensation

Periodic π-conjugated polymers of the group 16 heterocycles (furan, thiophene, and selenophene) were synthesized with controlled chain lengths and relatively low dispersities using catalyst-transfer polycondensation. The optical gap and redox potentials of these copolymers were fine-tuned by altering the heterocycle sequence, and atomic force microscopy revealed nanofibrillar morphologies for all the materials. Grazing incidence wide-angle X-ray scattering of the thiophene-selenophene copolymers indicated that the π-stacking distance increased with incorporation of the larger heteroatom (from ～3.7-4.0 ?), while the lamellar spacing decreased (from ～15.8-15.2 ?). The study also revealed that periodic sequences allow electronic properties to be tuned while retaining nanofibrillar morphologies similar to those observed for poly(3-hexylthiophene).

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

Efficient synthesis of a regioregular oligothiophene photovoltaic dye molecule, MK-2, and related compounds: A cooperative hypervalent iodine and metal-catalyzed synthetic route

We have successfully established an efficient route to the core structure of donor-acceptor head-to-tail (H-T)-linked regioregular oligothiophenes, which includes the following key synthetic steps, that is, hypervalent iodine induced direct and regioselec

"fibonacci's route" to regioregular oligo(3-hexylthiophene)s

We describe a new synthetic approach to regioregular monodisperse oligo(3-alkylthiophene)s allowing for simple separation of regioregular material in gram quantities. The number of repeat units follows the Fibonacci numbers up to a length of 21. In a small adaption of this approach, introduction of a protecting group was used to synthesize an oligo(3-hexylthiophene) with 36 repeating units, the longest regioregular 3-hexylthiophene oligomer synthesized to date.