3339-79-5

Usage

Type of compound

A halogenated derivative of bithiophene, a heterocyclic compound

Usage

Used as a building block in the synthesis of organic semiconductors and conducting polymers

Potential applications

Organic photovoltaics and organic light-emitting diodes

Importance

Unique molecular structure and electronic properties make it a valuable tool for researchers in the field of organic electronics and materials science.

Upstream product

• 492-97-7 2,2'-Bithiophene 

Downstream Products

• 1081-34-1 2,2':5',2''-terthiophene 
• 7342-41-8 2,2':5',2''-terthiophene-5-carboxaldehyde 
• 5660-45-7 quinquethienyl 
• 88493-55-4 sexithiophene 
• 1224710-22-8 2-[9,9-bis(n-decyl)-2-diphenylamino-7-fluorenyl]-bithiophene 
• 151271-42-0 2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene 
• 1134-61-8 5-but-3-en-1-ynyl-[2,2']bithiophenyl 
• 409093-85-2 diphenyl(2,2'-bithienyl-5-yl)phosphine 
• 4805-21-4 5-(2-phenylethynyl)-2,2'-bithiophene 

Relevant academic research and scientific papers

Synthesis of thiophene/phenylene co-oligomers. II [1]. Block and alternating co-oligomers

We report the synthesis of block and alternating thiophene/phenylene co- oligomers that is based either on the Suzuki coupling reaction or on the Grignard reaction. These reaction schemes enable us to obtain the target compounds at reasonably high yields.

One-pot, regioselective consecutive multihalogenation of 2,2′-bithiophene

The one-pot regioselective consecutive multihalogenation of 2,2′-bithiophene (1) was demonstrated. Compound 1 was consecutively halogenated with lithium halides such as lithium bromide, chloride, and/or iodide in the presence of lead tetraacetate in chloroform at room temperature or under reflux conditions to give 5-bromo(or chloro)-5′-iodo(or chloro)-, 3-bromo(or chloro)-5,5′-dibromo(or dichloro, diiodo)-, 3,3′-dibromo-(or dichloro)-5,5′-diiodo(or dibromo, dichloro)-, and 3,3′,5-tribromo(or trichloro)-5′-iodo(or bromo)-2,2′- bithiophenes. Notably, this process offers a regioselective method for consecutive multihalogenation in one pot, and the yields and selectivity are also higher than those obtained in the step-by-step and concurrent halogenation methods. Copyright

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent

The green generation of X+ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alcohol, nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochemistry were very similar to reactions involving N-bromosuccinimide in tetrahydrofuran solvent.

Polythiophene anti-tumor agents

Novel polythiophene compounds useful as anti-tumor agents are described. Preferred compounds of the formula: STR1 wherein n is 0-2 and R2 and R3 are optionally substituted 2-thienyl or 3-thienyl have been found to exhibit selective c