Overview
2,2'-Bipyridine-4,4'-dicarboxylic acid is a functionalized bipyridine derivative that serves as a versatile building block in coordination chemistry. Its rigid planar structure and dual carboxylate groups enable the formation of stable metal complexes and porous coordination polymers. The compound is particularly valued in materials science for constructing metal-organic frameworks (MOFs) with tunable porosity and catalytic activity. First synthesized in the late 20th century, this ligand has gained prominence in advanced applications ranging from molecular electronics to heterogeneous catalysis. Its ability to coordinate with various transition metals (Ru, Ir, Cu) makes it indispensable for designing photoactive materials and electrochemical sensors.
Physical and Chemical Properties
The compound exhibits high thermal stability with decomposition temperatures exceeding 300°C, making it suitable for high-temperature applications. Its limited solubility in water contrasts with good solubility in polar organic solvents like DMSO and methanol, which facilitates its use in solution-phase synthesis. The pKa values of the carboxyl groups (approximately 2.5 and 4.5) allow for pH-dependent coordination behavior. Characteristic IR absorption bands at 1700 cm-1 (C=O stretch) and 1550 cm-1 (pyridine ring vibrations) aid in material characterization. The ligand's redox-active nature enables electron transfer processes in catalytic systems, while its planar geometry promotes π-π stacking in supramolecular assemblies.
Main Applications
In catalysis, this ligand forms active complexes for C-H activation and water oxidation reactions, particularly with ruthenium centers. MOFs incorporating this linker demonstrate exceptional CO2 adsorption capacity (up to 120 cm3/g at STP) for carbon capture applications. The photovoltaic industry utilizes its metal complexes as charge-transfer sensitizers in dye-sensitized solar cells (DSSCs), achieving conversion efficiencies over 11%. Pharmaceutical researchers employ the compound to develop metal-based drugs, leveraging its ability to cross cell membranes when complexed with therapeutic ions. Analytical chemists use functionalized derivatives as fluorescent probes for metal ion detection with sub-ppm sensitivity.
Safety and Storage
As a fine powder, the compound requires handling in well-ventilated areas with appropriate respiratory protection (NIOSH N95 or equivalent). Spills should be contained using inert absorbents like vermiculite, followed by disposal as hazardous organic waste. Long-term storage necessitates amber glass bottles with PTFE-lined caps under nitrogen atmosphere to prevent degradation. Emergency procedures include flushing eyes with water for 15 minutes if exposed and removing contaminated clothing immediately. The material shows low acute toxicity (LD50 >2000 mg/kg oral, rat) but may cause sensitization upon repeated exposure. Safety Data Sheets (SDS) should be consulted for region-specific handling regulations.
B2B Procurement Guide
Industrial buyers should specify technical requirements including HPLC purity (typically 98-99.5%), heavy metal content (<10 ppm), and residual solvent levels. Bulk quantities (1kg+) often require 8-12 weeks lead time from specialty chemical manufacturers. Certificates of Analysis (CoA) should include 1H/13C NMR, HPLC chromatograms, and elemental analysis data. For MOF synthesis applications, particle size distribution (D90 <50μm) becomes critical. Some suppliers offer custom functionalization (e.g., ester protection) for specific applications. Logistics considerations include temperature-controlled shipping for international orders to prevent condensation-related degradation.
Related Manufacturers
- 主营：TE(泰科)、莫仕、德尔福、JAE、KET
- 主营：CFH-ALS、32004-B2、32004-A2、282404-1、171661-1、171662-1、770680-1、770520-1、174262-2、281934-4、连接器、端子