679844-18-9

Basic information

• Product Name: 2,2'-Bipyrimidine, 5,5'-diethynyl-
• CAS NO: 679844-18-9
• Molecular Formula: C12H6N4
• Molecular Weight: 206.206
• Mol File: 679844-18-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,2'-Bipyrimidine, 5,5'-diethynyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bipyrimidine, 5,5'-diethynyl-(679844-18-9)
• EPA Substance Registry System: 2,2'-Bipyrimidine, 5,5'-diethynyl-(679844-18-9)

Safety Data

• Hazardous Substances Data: 679844-18-9(Hazardous Substances Data)

Usage

General Description

2,2'-Bipyrimidine, 5,5'-diethynyl- is a chemical compound with the molecular formula C14H6N4. It is a member of the bipyrimidine class of compounds and is characterized by its two pyrimidine rings connected by a diethynyl bridge. 2,2'-Bipyrimidine, 5,5'-diethynyl- is commonly used in organic synthesis and materials science, where its unique structure and properties make it valuable for a variety of applications. It can be utilized as a ligand in coordination chemistry, serving as a chelating agent for metal ions, and in the construction of coordination polymers and metal-organic frameworks. Additionally, 2,2'-Bipyrimidine, 5,5'-diethynyl- has potential applications in optoelectronic devices, such as organic light-emitting diodes and organic photovoltaics, due to its conjugated structure and electronic properties. Overall, this compound is an important and versatile building block in the field of organic and materials chemistry.

Upstream product

• 34671-83-5 2,2'-Bipyrimidine 
• 400859-09-8 5,5′-dibromo-2,2′-bipyrimidine 
• 718606-28-1 5,5'-di(trimethylsilylethynyl)-2,2'-bipyrimidine 

Downstream Products

• 718606-37-2 5,5'-diethynyl-2,2'-bipyrimidine 

Relevant articles and documents

Photophysical properties of binuclear ruthenium(II) bis(2,2′: 6′,2″-terpyridine) complexes built around a central 2,2′-bipyrimidine receptor

A binuclear complex has been synthesized having ruthenium(II) bis(2,2′:6′,2″-terpyridine) terminals attached to a central 2,2′-bipyrimidine unit via ethynylene groups. Cyclic voltammetry indicates that the substituted terpyridine is the most easily reduced subunit and the main chromophore involves charge transfer from the metal centre to this ligand. The resultant metal-to-ligand, charge-transfer (MLCT) triplet state is weakly emissive and has a lifetime of 60 ns in deoxygenated solution at room temperature. The luminescence yield and lifetime increase with decreasing temperature in a manner that indicates the lowest-energy MLCT triplet couples to at least two higher-energy triplets. Cations can bind to the central bipyrimidine unit, forming both 1 : 1 and 1 : 2 (ligand : metal) complexes as confirmed by electrospray MS analysis. The photophysical properties depend on the number of bound cations and on the nature of the cation. In the specific case of binding zinc(II) cations, the 1 : 1 complex has a triplet lifetime of 8.0 ns while that of the 1 : 2 complex is 1.8 ns. The 1 : 1 complexes formed with Ba2+ and Mg2+ are more luminescent than is the parent compound while the 1 : 2 complexes are much less luminescent. It is shown that the coordinated cations raise the reduction potential of the central bipyrimidine unit and thereby increase the activation energy for coupling with the metal-centred state. Complexation also introduces a non-emissive intramolecular charge-transfer (ICT) state that couples to the lowest-energy MLCT triplet and provides an additional non-radiative decay route. The triplet state of the 1 : 2 complex formed with added Zn2+ cations decays preferentially via this ICT state. The Royal Society of Chemistry 2005.