211737-46-1

Usage

Uses

Used in Organic Electronics Industry:
5,5'-DIHEXYL-2,2'-BITHIOPHENE is used as a conductive additive for its ability to improve the charge transport properties of organic electronic materials. Its enhanced solubility and processing properties facilitate its integration into devices, enhancing their performance and reliability.
Used in Photovoltaic Devices:
In the photovoltaic industry, 5,5'-DIHEXYL-2,2'-BITHIOPHENE serves as a key component in improving the efficiency and stability of solar cells. Its role as a conductive additive aids in the optimization of charge transport, which is crucial for the performance of these energy-harvesting devices.
Used in Advanced Electronic Materials Development:
5,5'-DIHEXYL-2,2'-BITHIOPHENE is utilized as a foundational compound in the research and development of next-generation electronic materials. Its thermal stability and chemical resistance are particularly beneficial in creating materials that can withstand rigorous conditions and maintain their functionality over time.

Upstream product

• 18794-77-9 2-hexylthiophene 
• 790712-91-3 3-hexyl-5'-bromo-2,2'-dithiophene 
• 710338-91-3 2-n-hexyl-5-iodothiophene 

Downstream Products

• 1429918-64-8 N-(diphenylmethylene)-5,5'-dihexyl-2,2'-bithiophen-3-amine 

Relevant academic research and scientific papers

Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst

Substituted bithiophenes are prominent fragments in functional organic materials, and they are ideally prepared via direct oxidative C-H/C-H coupling. Here, we report a novel PdII catalyst system, employing 1,10-phenanthroline-5,6-dione (phd) as the ancillary ligand, that enables aerobic oxidative homocoupling of 2-bromothiophenes and other related heterocycles. These observations represent the first use of phd to support Pd-catalyzed aerobic oxidation. The reaction also benefits from a Cu(OAc)2 cocatalyst, and mechanistic studies show that Cu promotes C-C coupling, implicating a role for CuII different from its conventional contribution to reoxidation of the Pd catalyst.

Method for Aerobic Oxidative Coupling of Thiophenes with a Ligand-Supported Palladium Catalyst

An oxidative homocoupling method of synthesizing certain 2,2′-bithiophenes from thiophenes using oxygen as the terminal oxidant is disclosed. In non-limiting examples, the method uses oxygen along with a catalytic system that includes palladium, an assistive ligand, and a non-palladium metal additive to catalyze one of the following reactions: Associated catalytic systems and compositions are also disclosed.

Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides

We report herein an operationally simple homocoupling reaction that targets the convenient synthesis of organic-electronically important building blocks. A variety of synthetically useful bithiophene derivatives and functionalized biphenyls are efficiently prepared by an on-water and under-air protocol using Pd/C as catalyst. We find that Pd/C gives generally higher and cleaner homocoupling conversions than using Pd(OAc)2 in the cases of (hetero)aryl iodides since Pd(OAc)2 triggers more side reactions including dehalogenations and oligomerizations. Under the optimum conditions, a broad range of functional groups such as ester, ketone, aldehyde, nitrile, nitro, chloride, and bromide are well tolerated. We expect the present methodology would make a valuable synthetic contribution towards bridging green chemistry with thiophene-based organic materials.

Palladium-catalyzed C-H homocoupling of furans and thiophenes using oxygen as the oxidant

A general and efficient palladium-catalyzed intermolecular direct C-H homocoupling of furans and thiophenes has been developed. The reaction is characterized by using molecular oxygen as the sole oxidant and complete C5-position regioselectivity. Both C2- and C3-substituted furans or thiophenes are appropriate substrates. The approach provides a straightforward, facile, and economical route to bifurans and bithiophenes under mild reaction conditions.

Influence of alkyl chain length on the solid-state properties and transistor performance of BN-substituted tetrathienonaphthalenes

Flexible side chains have not drawn much attention in the development of organic semiconductors compared to the conjugated backbone counterparts. In this work, a series of BN-substituted tetrathienonaphthalenes (BN-TTNs) with methyl to hexyl side chains w

Azaborine compounds for organic field-effect transistors: Efficient synthesis, remarkable stability, and BN dipole interactions

Boron-nitrogen units were incorporated into thiophene-fused polycyclic aromatic compounds. Organic field-effect transistors based on these azaborine compounds were fabricated, demonstrating a novel engineering concept of organic semiconductors and providi

Aziridinofullerene: A Versatile platform for functionalized fullerenes

An aziridine moiety on the fullerene core can serve as an acid-triggered reacting template for the controlled synthesis of a range of functionalized fullerenes that are otherwise difficult to synthesize in an efficient and selective manner. A copper-catal

Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)4 generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G*ab initio calculations on 2,2′-bithiophene and the corresponding monoand bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the π,π* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.