133810-44-3

Basic information

• Product Name: 2,2'-Bipyridine, 4,4'-diethynyl-
• CAS NO: 133810-44-3
• Molecular Formula: C14H8N2
• Molecular Weight: 204.231
• Mol File: 133810-44-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2,2'-Bipyridine, 4,4'-diethynyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bipyridine, 4,4'-diethynyl-(133810-44-3)
• EPA Substance Registry System: 2,2'-Bipyridine, 4,4'-diethynyl-(133810-44-3)

Safety Data

• Hazardous Substances Data: 133810-44-3(Hazardous Substances Data)

Usage

Derivative of 2,2'-bipyridine

A compound based on 2,2'-bipyridine with added ethynyl groups

Addition of two ethynyl groups

The modification of the bipyridine molecule by attaching two ethynyl groups at the 4 and 4' positions

Conjugated organic materials

Materials with alternating single and double bonds that can absorb and emit light in the visible spectrum

Building block for molecular structures

A basic unit used to construct more complex molecules with specific functions or properties

Unique structure and properties

The combination of the bipyridine core and added ethynyl groups give this compound distinctive characteristics that may be useful in various applications.

Upstream product

• 51595-55-2 4,4'-dinitro-2,2'-bipyridyl-N,N'-dioxide 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 366-18-7 [2,2]bipyridinyl 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 99970-84-0 [2,2']bipyridinyl-4,4'-dicarbaldehyde 
• 1019994-51-4 4,4’-bis[2,2'-(triisopropylsilyl-ethynyl)]-2,2'-bipyridine 
• 18511-71-2 4,4'-dibromo-2,2'-bipyridine 
• 133810-43-2 4,4'-bis<2-(trimethylsilyl)-1-ethynyl>-2,2'-bipyridine 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 449144-83-6 thioacetic acid S-{4-[4'-(4-acetylsulfanyl-phenylethynyl)-[2,2']bipyridinyl-4-ylethynyl]-phenyl} ester 
• 1019994-53-6 4,4'-bis(1,2,3,4-tetraphenylphen-6-yl)-2,2'-bipyridyl 
• 1019994-55-8 4,4'-bis(1,4-diphenyl-2,3-((p-TiPS-ethynyl)phenyl)phen-6-yl)-2,2'-bipyridyl 
• 1297609-44-9 4,4'-bis(1-benzyl-1H-[1,2,3]triazol-4-yl)-[2,2']bipyridinyl 
• 1437656-49-9 4,4'-diethynyl-2,2'-bipyridine 
• 1437656-46-6 4,4'-diethynyl-2,2'-bipyridine 
• 1222368-88-8 4,4'-bis(1-(4-(hexyloxy)phenyl)-1H-1,2,3-triazol-4-yl)-2,2'-bipyridine 
• 1222368-87-7 4,4'-bis(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)-2,2'-bipyridine 
• 390366-08-2 4,4'-bis[(4-(N,N-diethylcarboxamido)phenyl)ethynyl]-2,2'-bipyridinyl 

Relevant articles and documents

Towards Ruthenium-Based Building Blocks for CuAAC Click Reactions: Challenges in Generating Ruthenium(II) Polypyridine Alkynes

Ag+-free complexation of alkyne-bipyridines at ruthenium(II) polypyridine centers proceeds with surprisingly low yields. The alkyne-bipyridine-substituted ruthenium(II) polypyridine complexes in this work were characterized by NMR spectroscopy, ESI spectrometry, and single-crystal X-ray structural analysis. A detailed analysis of the side products revealed an unexpected carbon-carbon alkyne bond splitting promoted by the ruthenium(II) center, leading to the formation of a CO-RuII species, methyl-bipyridine, and a methyl-bipyridine-substituted ruthenium(II) complex accompanying the target product. The side products were characterized using complimentary methods including X-ray crystallography. A possible mechanism is suggested based on these side products and exemplary reaction studies. For the coordination reaction of alkyne-bipyridines with Ru(bpy)2Cl2 unexpected side reactions take place, forming a RuII-CO species and methyl-bipyridine. Here we give a detailed mechanism of the side reactions and an adequate workup procedure to obtain a pure alkyne-substituted ruthenium(II) polypyridine complex, which is the intended product.

Highly efficient benzodifuran based ruthenium sensitizers for thin-film dye-sensitized solar cells

The synthesis of 4,4′-dibenzodifuran-2,2′-bipyridine derivatives as ligands of organic ruthenium dyes for DSSC applications is described. Two new heteroleptic ruthenium complexes have been prepared and compared with commercially available N719 and Z907 dyes, using dip dyeing and flow dyeing methods in large area testing cells prepared for industrial purposes. The newly synthesized dyes revealed higher solar-to-electric energy conversion efficiency (η), measured at the AM1.5G conditions, up to 21% compared to N719 and up to 46% compared to Z907, and external quantum efficiency of 53%. These results can be explained by enhanced light-harvesting of the benzodifuran moiety of the dyes that is related to photocurrent.

A modular 'click' approach to substituted 2,2′-bipyridines

The CuAAC reaction was used for the development of a click approach to a series of triazole-substituted bipyridinyl derivatives. 4,4′-Diethinyl 2,2′-bipyridine and 4,4′-diazido 2,2′-bipyridine were synthesized and tested in the cycloaddition reactions. While 4,4′-diazido 2,2′-bipyridine revealed unreactive in CuAAC reactions, its corresponding N,N′-dioxide afforded the expected cycloaddition product. Georg Thieme Verlag Stuttgart.