679844-18-9

Usage

Uses

Used in Organic Synthesis and Materials Science:
2,2'-Bipyrimidine, 5,5'-diethynylis used as a versatile building block for the synthesis of various organic compounds and materials. Its unique structure and properties contribute to the development of new materials with desired characteristics.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, 2,2'-Bipyrimidine, 5,5'-diethynylis used as a chelating agent for metal ions. It forms stable complexes with metals, which are essential for various applications, such as catalysis and sensing.
Used in the Construction of Coordination Polymers and Metal-Organic Frameworks:
2,2'-Bipyrimidine, 5,5'-diethynylplays a crucial role in the construction of coordination polymers and metal-organic frameworks (MOFs). These materials have potential applications in gas storage, separation, and catalysis due to their high porosity and tunable properties.
Used in Optoelectronic Devices:
2,2'-Bipyrimidine, 5,5'-diethynylhas potential applications in optoelectronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Its conjugated structure and electronic properties make it suitable for these applications, where efficient charge transport and light emission are required.

Upstream product

• 400859-09-8 5,5′-dibromo-2,2′-bipyrimidine 
• 34671-83-5 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 academic research and scientific papers

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.

Segmented multitopic ligands constructed from bipyrimidine, phenanthroline, and terpyridine modules

Starting from bromo-substituted 2,2′-bipyrimidine or 1,10-phenanthroline building blocks, the preparation in a first step of ethynyl grafted molecules allows the production in a second step of multitopic ligands by cross-coupling with difunctionalised chelating molecules. Various combinations allow the interconnection of bipyrimidine to terpyridine, pyrene, or phenanthroline fragments. When two alkyne functions are present, a simple protocol gives a large variety of linear or bent ligands with an increasing number of nitrogen atoms. It was also possible to construct a linear complex capped at the periphery by ruthenium(II) centers and retaining an uncomplexed phenanthroline fragment in its core.