211737-46-1

Basic information

• Product Name: 5,5'-DIHEXYL-2,2'-BITHIOPHENE
• Synonyms: DH-2T
• CAS NO: 211737-46-1
• Molecular Formula: C20H30S2
• Molecular Weight: 334.58
• Mol File: 211737-46-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 29-33 °C(lit.)
• Boiling Point: 414.8±40.0 °C(Predicted)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.009±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5,5'-DIHEXYL-2,2'-BITHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-DIHEXYL-2,2'-BITHIOPHENE(211737-46-1)
• EPA Substance Registry System: 5,5'-DIHEXYL-2,2'-BITHIOPHENE(211737-46-1)

Safety Data

• Hazardous Substances Data: 211737-46-1(Hazardous Substances Data)

Usage

General Description

5,5'-dihexyl-2,2'-bithiophene is a chemical compound consisting of two aromatic rings linked by a sulfur atom and with hexyl substituents on each ring. It belongs to the bithiophene family of compounds, which are commonly used in various electronic applications due to their excellent charge transporting properties. This particular compound, with its long alkyl chains, has improved solubility and processing properties, making it suitable for use as a conductive additive in organic electronics and photovoltaic devices. Additionally, its high thermal stability and chemical resistance make it a promising candidate for use in various organic electronic applications. Overall, 5,5'-dihexyl-2,2'-bithiophene is a valuable chemical compound for the development of advanced electronic materials.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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