172514-63-5

Basic information

• Product Name: 2-BroMo-5-n-octylthiophene
• Synonyms: 2-BroMo-5-n-octylthiophene;2-bromo-5-octylThiophene;2-Bromo-5-n-octylthiophene
• CAS NO: 172514-63-5
• Molecular Formula: C₁₂H₁₉BrS
• Molecular Weight: 275
• Mol File: 172514-63-5.mol

Chemical Properties

• Melting Point: 5°C(lit.)
• Boiling Point: 112°C/0.2mmHg(lit.)
• Appearance: /
• Refractive Index: 1.5180-1.5220
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 2-BroMo-5-n-octylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BroMo-5-n-octylthiophene(172514-63-5)
• EPA Substance Registry System: 2-BroMo-5-n-octylthiophene(172514-63-5)

Safety Data

• Hazardous Substances Data: 172514-63-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
2-Bromo-5-n-octylthiophene is used as a key building block for the synthesis of conducting polymers and semiconducting materials. Its unique structure allows for the creation of organic electronic devices with improved performance and stability.
Used in Organic Solar Cells:
2-Bromo-5-n-octylthiophene is employed as a component in the development of organic solar cells, where its electronic properties contribute to the efficiency and stability of the solar cell devices.
Used in Light-Emitting Diodes (LEDs):
2-BroMo-5-n-octylthiophene is utilized in the production of light-emitting diodes, where its electronic properties play a crucial role in the performance and efficiency of the LEDs.
Used in Field-Effect Transistors:
2-Bromo-5-n-octylthiophene is used as a material in the fabrication of field-effect transistors, where its electronic properties are essential for the device's operation and performance.
Used for Functionalization and Surface Modification:
In the field of organic electronics, 2-Bromo-5-n-octylthiophene serves as a building block for the functionalization and surface modification of materials, enabling the development of advanced electronic devices with tailored properties and improved performance.

Upstream product

• 880-36-4 2-octylthiophene 
• 111-83-1 1-bromo-octane 

Downstream Products

• 925424-90-4 4,4,5,5-tetramethyl-2-(5-octylthiophen-2-yl)-1,3,2-dioxaborolane 
• 93164-73-9 5-octyl-2,2’-bithiophene 

Relevant articles and documents

Synthesis of Functionalized Carbon-Sulfur [5]Helicene: Pd-Catalyzed Negishi Cross-Coupling between the β-Positions of Thiophenes

Octyl- and bromo-substituted carbon-sulfur [5]helicene was prepared in several steps starting from either thiophene or 3-bromothiophene. Pd-catalyzed Negishi cross-coupling between the β-positions of thiophenes was one of the key steps in the synthesis.

The new and simple 'LEGO' System: Synthesis and reactions of ruthenium(II) complexes

The synthesis of ruthenium(II) complexes with 2,2'-bipyridine and 1,10- phenanthroline as ligands is described. These ligands were prepared using reactions of our new and simple 'LEGO' Systems. 'LEGO' system reactions which are possible with the free, uncoordinated ligands also apply to coordinated ligands.

Synthesis and optical properties of soluble near-infrared arylene bisthienoimidazole dyes

Soluble, film-forming near-infrared arylene bisthienoimidazole dyes with a band gap of 1.2-1.3 eV are electrochromic and absorb strongly at the telecommunication wavelengths (1310 and 1550 nm) in the oxidized state.

The steric effect of benzodifuran based polymers: Via alkyl side chain manipulation: A simple approach for enhancing the photovoltaic performance

A series of narrow band gap conjugated copolymers with different alkyl side chains were synthesized via Stille copolymerization of benzodifuran (BDF) and benzothiadiazole (BT) monomers. The origination effect of the alkyl side chains, linked to the thienyl side groups of BDF based backbone, on the optical, electronic and morphological properties of the resulting polymers were investigated and correlated with the photovoltaic performance. It was found that the different alkyl side chains positions have a significant impact on the polymeric optoelectronic properties due to differences of torsion in the backbones. The best performance of the bulk-heterojunction solar cells (BHJ) with a power conversion efficiency (PCE) of 6.73% was achieved with PBFDBT-o as the donor and (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) as the acceptor, which can be attributed to its higher charge carrier mobility as well as the optimized interpenetrating network with respect to the other two polymers. The results demonstrated that the alkyl side chain position manipulations play a crucial role in adjusting the optoelectronic properties of BDF based copolymers and it is a promising molecular design strategy for the application of solar cells.

Controllable morphology and self-assembly of one-dimensional luminescent crystals based on alkyl-fluoro-substituted dithienophenazines

A class of dithienophenazine derivatives, 9,10-difluoro-2,5-dialkyldithieno[3,2-a:2′,3′-c]phenazine (F-n, n = 4, 5, 6, 7 and 8), modified with various lengths of linear alkyl chains were synthesized and used as building blocks to assemble luminescent one-dimensional (1D) nano/microcrystals. It was demonstrated that the side-chain length can dramatically influence the self-assembled morphologies of the 1D nano/micromaterials. The self-assembly behaviors of F-n have been studied based on the methods of crystallization in the solution phase and solvent evaporation on a substrate. For F-4, F-6 and F-7 molecules, well-defined 1D twisted microstructures (including ribbons, fibers and bundles) were obtained. F-5 molecules can self-assemble into nearly criss-cross (orthogonal) network patterns interconnected by 1D wires. F-8 molecules with longer alkyl chains predominantly formed flattened wires. Single crystal X-ray structure studies of F-n (n = 4, 5 and 8) demonstrated that alkyl chains with different lengths result in distinctly different intermolecular interactions and molecular packing modes, which provides a reasonable explanation for the alkyl chain length-dependent assembly morphologies and emission of F-n-based nano/micromaterials. It has been demonstrated that anisotropic noncovalent interactions and mirror-symmetrical crystallization dominated the 1D assembly behaviors of this class of molecules.

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.

ORGANIC SEMICONDUCTOR MATERIAL, ORGANIC SEMICONDUCTOR STRUCTURE AND ORGANIC SEMICONDUCTOR APPARATUS

The present invention is directed to the provision of a liquid crystalline organic semiconductor material, which is highly stable under a film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material comprises: a thiophene skeleton comprising 3 to 6 thiophenes linearly connected to each other; and an identical alkyl group having 1 to 20 carbon atoms located on both sides of the thiophene skeleton, wherein acetylene skeletons each have been introduced into between the thiophene skeleton and the alkyl group, or acetylene skeletons have been introduced symmetrically into the thiophene skeleton.

Non-symmetrical oligothiophenes with 'incompatible' substituents

The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods.

Nematic 2,5-disubstituted thiophenes

A large number of new liquid crystals incorporating the 2,5-disubstituted thiophene ring have been prepared and their mesomorphic behaviour studied in order to systematically investigate the correlation between the molecular structure and mesomorphism of thiophene derivatives with different shapes, polarisability and polarity. As a consequence of these investigations we have prepared a new class of liquid crystals incorporating a 2,5-disubstituted thiophene ring and a conjugated trans-carbon-carbon double bond in the terminal chain. These novel thiophene derivatives are the first liquid crystals incorporating a 2,5-disubstituted thiophene ring to exhibit a nematic phase at room temperature. This enables the flexoelectric coefficients of a bent-shaped molecule to be measured directly and at room temperature for the first time to the authors' knowledge. Many of these new thiophenes exhibit a high birefringence and a high nematic clearing point and are of potential use as components of nematic mixtures in LCDs.

Nematic thiophenes for STN-LCDS and flexoelectric LCDS

We report anew class of liquid crystals incorporating a 2,5-disubstituted thiophene ring and one or two conjugated trans-carbon-carbon double bonds in the terminal chain for use as components of nematic mixtures for TN-LCDs and STN-LCDs. The combination of these molecular elements contribute towards generating a high birefringence, a high nematic clearing point as well as a low viscosity for these materials. Several of these compounds exhibit a melting point below room temperature. This is the first time a room temperature nematic phase has been reported for phenyl thiophene derivatives. The new thiophene compounds can be used to induce a high birefringence in nematic mixtures for LCDs with short response times.