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
• Article Data: 29

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

General Description

3,4'-Dihexyl-2,2'-bithiophene is a chemical compound with a molecular formula of C18H26S2. It is a bithiophene derivative that consists of two thiophene rings with hexyl groups attached at the 3 and 4' positions. 3,4'-Dihexyl-2,2'-bithiophene is commonly used as a semiconductor material in organic electronic devices such as organic field-effect transistors and organic photovoltaic cells due to its high electron mobility and stability. Its long alkyl chains contribute to its solubility in organic solvents, making it suitable for solution-processing methods. This chemical compound has attracted significant research interest in the development of advanced electronic and optoelectronic devices.

Upstream product

• 69249-61-2 3-hexyl-2-bromothiophene 
• 1693-86-3 3-hexylthiophene 
• 817181-75-2 2-chloro-3-(n-hexyl)-thiophene 
• 154717-22-3 (3-hexylthiophene-5-yl)trimethylstannane 
• 444579-42-4 tributyl(4-hexyl-2-thienyl)stannane 
• 883742-29-8 2-(4-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 210705-84-3 2-bromo-4-n-hexylthiophene 
• 3761-92-0 n-hexylmagnesium bromide 
• 1220778-17-5 (3-hexylthiophen-2-yl)magnesium chloride 
• 126298-17-7 (4-hexylthiophen-2-yl)magnesium chloride 
• 850881-09-3 3-hexylthiophene-2-boronic acid pinacol ester 
• 691006-31-2 triethyl-[3-(n-hexyl)thiophen-2-yl]silane 
• 691006-33-4 tert-butyl-[3-(n-hexyl)thiophen-2-yl]dimethylsilane 
• 618887-45-9 tert-butyl-[4-(n-hexyl)thiophen-2-yl]dimethylsilane 

Downstream Products

• 154717-19-8 5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene 
• 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 
• 1432475-93-8 4-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]phenylmorpholine 
• 1432475-92-7 4-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]-N,N-diphenylbenzenamine 

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.

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.

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).

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.