1245-13-2

Usage

Uses

Used in Chemical Research and Synthesis:
2,2'-BICINCHONINIC ACID is used as a chemical intermediate for the synthesis of metal-organic coordination polymers. In a study, it was utilized to synthesize and structurally characterize six different metal-organic coordination polymers, showcasing its potential in the development of new materials with unique properties.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2,2'-BICINCHONINIC ACID, due to its chemical structure, could potentially be used in the pharmaceutical industry as a building block for the development of new drugs or as a reagent in drug synthesis processes. Its ability to form coordination polymers with metal ions may also contribute to the design of novel drug delivery systems or therapeutic agents.
Used in Material Science:
2,2'-BICINCHONINIC ACID can be employed in material science for the creation of new materials with specific properties. Its role in the synthesis of metal-organic coordination polymers indicates that it could be instrumental in developing materials with applications in areas such as catalysis, sensing, or energy storage.

Purification Methods

Dissolve the acid in dilute NaOH and precipitate it with acetic acid, filter, wash swell with H2O and dry it at 100o in a vacuum oven. Attempts to form a picrate failed. The methyl ester (SOCl2-MeOH) has m 165.6-166o. [Lesesne & Henze J Am Chem Soc 64 1897 1942, Brown et al. J Am Chem Soc 68 2705 1946, Beilstein 25 III/IV 1148.] For the di-K salt see entry in “Metal-organic Compounds” in Chapter 5.

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 5743-04-4 cadmium(II) acetate dihydrate 
• 91-56-5 indole-2,3-dione 
• 431-03-8 dimethylglyoxal 
• 4091-39-8 3-chloro-2-butanone 
• 513-86-0 3-hydroxy-2-butanon 

Downstream Products

• 912-84-5 4,4'-diethylester-2,2'-biquinoline 
• 910-78-1 2,2′-biquinoline-4,4′-dimethyl ester 
• 1088610-72-3 dimethyl 2-(cyclohexylamino)-5-[cyclohexyl({2-[4-({cyclohexyl[5-(cyclohexylamino)-3,4-bis(methyloxycarbonyl)-2-furyl]amino}carbonyl)-2-quinolyl]quinolyl}carbonyl)amino]-3,4-furandicarboxylate 
• 1088610-74-5 diethyl 2-(cyclohexylamino)-5-[cyclohexyl({2-[4-({cyclohexyl[5-(cyclohexylamino)-3,4-bis(ethyloxycarbonyl)-2-furyl]amino}carbonyl)-2-quinolyl]quinolyl}carbonyl)amino]-3,4-furandicarboxylate 

Relevant academic research and scientific papers

Spectroscopic and electrochemical study of dinuclear and mononuclear copper complexes with the bidentate ligand of the 2,2′-diquinoline series

The newly synthesized complex (2) of copper(I) chloride with di-n-hexyl 2,2'-biquinoline-4,4'-dicarboxylate (L) was spectroscopically and electrochemically characterized. The X-ray diffraction study showed that the crystals of complex 2 consist of the dinuclear moieties [L2Cu 1 2(μ-Cl)2] containing Cu 2(μ-Cl)2 clusters. Spectrophotometric studies and ESI-mass spec-trometric measurements showed that after the dissolution of complex 2 in acetonitrile (AN) and N-methyl-2-pyrrolidone (NMP), the solution contained not only the dinuclear complexes [L2Cu1 2(μ-Cl)2] but also [L2Cu1]Cl, [LCu1Cl(Sol)], and [Cu1Cl(Sol)] (Sol is the solvent). The electrochemical data also confirm the conclusion that bridged dinuclear chloride complex 2 dissociates both in NMP and AN to form the tetrahedral bis-biquinoline complex [L2Cu1]Cl. In solutions of complex 2 in alcohols and N,N-dimethylformamide (DMF), only [L2Cu1]Cl and [Cu1Cl(Sol)] are present. In EtOH, AN, and DMF, [Cu1Cl(Sol)] undergoes disproportionation to [Cu11Cl(Sol)] and Cu0.

Biquinolino-modified β-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids

A series of bridged β-cyclodextrin (β-CyD) dimers possessing functional tethers of various lengths was synthesized in moderate yield by the treatment of 2,2′-biquinoline-4,4′-dicarboxylic dichloride with β-CyD or mono[6-oligo(ethylenediamino)-6-deoxy]-β-CyDs. The products were 2,2′-biquinoline-4,4′-dicarboxy-bridged bis(6-O-β-CyD) (8), N,N′-bis(2-aminoethyl)-2,2′-biquinoline-4,4′- dicarboxamide-bridged bis(6-amino-6-deoxy-β-CyD) (9), and N,N′-bis(5-amino-3-azapentyl)-2,2′-biquinoline-4, 4′-dicarboxamide-bridged bis(6-amino-6-deoxy-β-CyD) (10). The reaction of 8-10 with copper perchlorate give their copper(II) complexes 11-13 in satisfactory yields of over 77%. All the bis(β-CyD)s 8-13 act as efficient fluorescent sensors and display remarkable fluorescence enhancement upon addition of optically inert steroids. The inclusion complexation behaviors of 8-13 when treated with the representative steroids cholate (14), deoxycholate (15), and glycocholate (16) in aqueous solution at 25 °C were investigated by means of UV/Vis spectroscopy, conductivity and fluorescence measurements, circular dichroism spectroscopy, and 2D NMR spectroscopy. The tether length of bis(β-CyD) 9 allows it to adopt a cooperative host-tether-guest binding mode in which the spacer and guest are co-included in the two CyD cavities. As a result of this cooperation, 9 has a stability constant (Ks) about 2 × 102 times higher than that of monomodified β-CyD 4 for inclusion complexation with cholate. Metallooligo(β-CyD)s with four β-CyD units have enhanced binding abilities compared with monomodified β-CyDs. These metallo compounds have binding affinities for guest steroids that are up to 50-4.1 × 103 times higher than those of CyDs 2-4. The guest-induced fluorescence enhancement of bis(CyD)s opens a new channel for the design of sensor materials. The complex stability constants of these compounds are discussed from the viewpoint of induced-fit interaction and cooperative multiple binding between host and guest.

Synthesis, structure, and characterization of a new metal-organic framework containing meso-helices

The new metal-organic framework [Cd(bqdc)(phen)]n (1) (bqdc = 2, 2'-biquinoline-4, 4'-dicarboxylate, phen = 1, 10-phenanthroline) was hydrothermally synthesized by hetero-ring carboxylate ligand and N-containing auxiliary ligand. The structure of 1 was determined by single-crystal X-ray diffraction analysis and further characterized by elemental analyses, IR spectroscopy, X-ray powder diffraction, and TG analysis. Single-crystal X-ray structural analysis shows that complex 1 is an infinite two-dimensional framework containing aesthetic meso-helix. These two-dimensional coordination networks are interconnected through aromatic π-π stacking and C-H...O hydrogen bonding interactions to afford a 6-connected (412.6 3) three-dimensional supramolecular architecture. Furthermore, the photoluminescent property of complex 1 was studied. Copyright