880-36-4

Usage

Uses

Used in Organic Electronics Industry:
2-N-OCTYLTHIOPHENE is used as a key component in the production of organic electronic devices for its high charge carrier mobility and solubility. This makes it suitable for applications in field-effect transistors and organic photovoltaics, where efficient charge transport and processing are crucial.
Used in Organic Light-Emitting Diodes (OLEDs):
2-N-OCTYLTHIOPHENE is utilized as a material in the development of OLEDs due to its electronic properties, which contribute to the efficient emission of light in these devices.
Used in Chemical Sensors:
2-N-OCTYLTHIOPHENE is also studied for its potential application in chemical sensors, where its unique electronic properties can be harnessed to detect specific chemical substances or changes in the environment.

InChI:InChI=1/C12H20S/c1-2-3-4-5-6-7-9-12-10-8-11-13-12/h8,10-11H,2-7,9H2,1H3

Upstream product

• 188290-36-0 thiophene 
• 111-83-1 1-bromo-octane 
• 777952-08-6 8-[2]thienyl-octan-2-one 
• 30711-41-2 1-(thiophen-2-yl)octan-1-one 
• 629-27-6 1-Iodooctane 
• 693-04-9 butyl magnesium bromide 
• 69340-26-7 2-(4-Bromobutyl)-thiophene 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 
• 110-52-1 1,4-dibromo-butane 
• 109-99-9 tetrahydrofuran 
• 68-12-2 N,N-dimethyl-formamide 
• 111-64-8 n-octanoic acid chloride 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 3437-95-4 2-Iodothiophene 

Downstream Products

• 13090-49-8 dithieno[3, 4-b:3',4'-d]thiophene 
• 86373-15-1 4-[(5-Octyl-thiophen-2-ylmethyl)-amino]-benzoic acid 
• 86373-14-0 ethyl 4-{[(5-octyl-2-thienyl)methyl]amino}benzoate 
• 15594-90-8 n-henicosanol 
• 6064-90-0 methyl heneicosanoate 
• 13910-16-2 n-octylsulfanylbenzene 
• 93164-73-9 5-octyl-2,2’-bithiophene 
• 1258753-81-9 C₅₂H₅₄O₈S₂ 
• 925424-90-4 4,4,5,5-tetramethyl-2-(5-octylthiophen-2-yl)-1,3,2-dioxaborolane 
• 172514-63-5 2-bromo-5-octan-1-yl-thiophene 
• 90619-88-8 5-Octyl-2-thiophenecarboxylic acid 

Relevant academic research and scientific papers

Rational Design of an Iron-Based Catalyst for Suzuki–Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles

Suzuki–Miyaura cross-coupling reactions between a variety of alkyl halides and unactivated aryl boronic esters using a rationally designed iron-based catalyst supported by β-diketiminate ligands are described. High catalyst activity resulted in a broad substrate scope that included tertiary alkyl halides and heteroaromatic boronic esters. Mechanistic experiments revealed that the iron-based catalyst benefited from the propensity for β-diketiminate ligands to support low-coordinate and highly reducing iron amide intermediates, which are very efficient for effecting the transmetalation step required for the Suzuki–Miyaura cross-coupling reaction.

Synthesis of 1,3,6,8-tetra-substituted pyrene derivatives and application of pyrene derivatives in organic field-effect transistors

The invention aims to develop synthesis of 1,3,6,8-tetra-substituted pyrene derivatives of the same category having semiconductor properties and application of the derivatives in organic field-effecttransistors. Series thiophene units are introduced into positions 1, 3, 6 and 8 of pyrene to construct the tetra-substituted pyrene derivatives, and material preparation is performed by utilizing a chemical reaction. Moreover, a silicon wafer serves as a gate, and the pyrene derivatives serve as organic semiconductor materials, so that bottom-gate top-contact field-effect transistors are prepared.R refers to the following groups as shown in the specification.

1,8-Substituted Pyrene Derivatives for High-Performance Organic Field-Effect Transistors

There have been many reports on the application of pyrene derivatives as organic semiconductors, but 1,8-subsituted pyrene semiconductors are less well-developed. Two p-type 1,8-substituted pyrene derivatives were synthesized that were composed of a pyrene core, thiophene or bithiophene arms, and end-capped octyl chains. These structures were not completely symmetrical and the dihedral angles between the pyrene core and the adjacent thiophene units had a difference of approximately two degrees. The field-effect performance of these materials was tested on a variety of dielectric surfaces. The performance of both materials with a spin-coated polystyrene layer on SiO2 (PS-treated SiO2) was better than that with an octadecyltrichlorosilane self-assembled monolayer on SiO2 (OTS-treated SiO2), which was mainly attributed to the presence of large grains on the low-leakage and high-capacitance PS films. The thiophene-contained compound presented a hole mobility of up to 0.18 cm2 V?1 s?1 on PS-treated SiO2, which was 45 times that of the bithiophene-contained compound, owing to less steric hindrance, high crystallinity, and large grain size.

Cross-coupling reaction of alkyl halides with alkyl grignard reagents catalyzed by cp-iron complexes in the presence of 1,3-butadiene

Iron-catalyzed cross-coupling reaction of alkyl halides with alkyl Grignard reagents by the combined use of cyclopentadienyl ligand and 1,3-butadiene additive is described. The reaction smoothly proceeds at room temperature using unactivated alkyl bromides and fluorides via non-radical mechanism, which is in sharp contrast with hitherto known Fe-catalyzed cross-coupling reactions of alkyl halides.

Thiophene-containing thiolato dimers, oxygen inserted Cu(II) complex, crystal structures, molecular docking and theoretical studies

Reactions of n-butyl- and n-octyl-thiophene with CS2 at 0?°C resulted in thiolate dimers 1 and 2, respectively. The reaction of 1 with Cu(NO3)2·3H2O in methanol under ambient reaction conditions yielded monomeric [CuII{(n-C4H9(C4H2S)CS2O}2] (3). 1 and 3 were authenticated by their single-crystal X-ray crystal structures. Crystal structure of 3 revealed cleavage of the S-S bond of 1 followed by insertion of O-atom, forming a new five-membered Cu–O–S–C–S metallacycle. 1, 2, and 3 were further investigated for their bioactivity through molecular docking with nine different proteins having medicinal implications. Molecular docking of 1, 2 and 3 revealed considerable interaction with different proteins viz. cancer protein Tankyrase 2, influenza viral protein Polymerase subunit PAC–PB1N complex (H5N1), Polymerase subunit PA endonuclease (H1N1), Polymerase subunit PAn Apo(avian influenza), and FTSZ (Bacillus subtilis). Comparatively, 1 has promising application in therapeutics as compared to 2 and 3 based on its inhibitory constant and binding energy. Density functional theory calculations were performed to better understand the bonding of complex using MO diagram in 1–3. Moreover, TDDFT calculations were performed to facilitate the assignment of electronic transitions of UV–Vis spectra.

Boron fluoride complexing bi-pyrrole methylidyne derivative substituted by meso-position alkyl thiophene and 3,5-position electron-donating group and preparation method of derivative

The invention discloses a boron fluoride complexing bi-pyrrole methylidyne derivative substituted by meso-position alkyl thiophene and a 3,5-position electron-donating group and a preparation method of the derivative. According to the method, 2-bromothiophene serves as a starting raw material, dipyrrylmethanes substituted by meso-position alkyl thiophene is synthesized through a series of reactions, NBS bromination is conducted, and 3,5-dibromo bi-pyrrolidine is obtained; then, TCQ oxidation and boron trifluoride ether complexing are conducted, a 3,5-boron dibromo fluorine intermediate with the meso-position containing alkyl thiophene is obtained, then the intermediate is utilized to conduct an Suzuki/Stille coupled reaction with a variety of modification groups, the boron fluoride complexing bi-pyrrole methylidyne derivative substituted by a 3,5-position donor unit is obtained, and the structural formula can be found in formula I. The boron fluoride complexing bi-pyrrole methylidyne derivative substituted by meso-position alkyl thiophene and the 3,5-position electron-donating group has good stability and has potential application value in the fields of life science, solar cells, environment, energy and the like.

Metal complex, and dye sensitizing oxide semiconductor dye-sensitized solar power cell (by machine translation)

PROBLEM TO BE SOLVED: To provide a photoelectric conversion element using new dye, having sensitivity to light in a long-wavelength region, being stable, and having the conversion efficiency higher than that of the Black dye. SOLUTION: As the dye, a metal complex uses an organic metal dye represented by the following general formula (1): MLZX (1). In the formula, M represents a group VIII to X metal element, Z represents a 2,2'-6',2"-terpyridine dielectric having one to three carboxyl groups, X represents a halogen atom and a cyano group and the like, and L represents a 1,3-butanedione dielectric. COPYRIGHT: (C)2012,JPO&INPIT

Synthesis and characterization of two new benzothiadiazole- and fused bithiophene based low band-gap D-A copolymers: Application as donor bulk heterojunction polymer solar cells

Two new narrow bandgap D-A conjugated copolymers P1 and P2 containing different fused thiophene donor unit and same benzothiadiazole acceptor unit were synthesized by Stille cross-coupling polymerization, and characterized by 1H NMR, elemental analysis and GPC, TGA, DSC. Cyclic voltammetry measurement showed that the HOMO energy level both copolymers is deep lying (-5.10 and -5.35 eV for P1 and P2, respectively) which show that copolymers has good stability in the air and assured a higher open circuit voltage when it photovoltaic application. These copolymer were used as donor along with PC71BM and the BHJ polymer solar cells based on P1:PC71BM and P2:PC71BM processed with chloroform (CF) solvent showed over all PCE of 4.54% and 4.36%, respectively. Additionally, the PCE was improved up to 5.62% and 5.24% for P1:PC71BM and P2:PC71BM active layer processed with DIO (4 v%)/CF solvent. The enhancement in the PCE has been attributed to improved nanoscale morphology and crystalline nature of active layer as well as charge transport in the device with the addition of DIO, due to the higher boiling point of DIO causing slow evaporation rate during the film formation.

Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: Efficiency of catalyst and roles of additives

Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions.

OLIGOTHIOPHENES DERIVATIVES

The present invention is directed to new oligothiophene derivatives and their use as a semiconductor material in electronic devices. More specifically, the present invention relates to new 3,4-dicyanooligothiophenes derivatives, processes for manufacturing thereof, and to their use as organic n-type (electron-transporting) semiconductors, in particular, in field-effect transistors (FET).