322637-99-0

Basic information

• Product Name: 2,4,6-tris(2-pyridyl)pyridine
• Synonyms: 322637-99-0
• CAS NO: 322637-99-0
• Molecular Formula: C₂₀H₁₄N₄
• Molecular Weight: 310.352
• Mol File: 322637-99-0.mol

Chemical Properties

• Boiling Point: 485.257°C at 760 mmHg
• Flash Point: 215.902°C
• Density: 1.202g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2,4,6-tris(2-pyridyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-tris(2-pyridyl)pyridine(322637-99-0)
• EPA Substance Registry System: 2,4,6-tris(2-pyridyl)pyridine(322637-99-0)

Safety Data

• Hazardous Substances Data: 322637-99-0(Hazardous Substances Data)

Upstream product

• 4744-02-9 C₁₃H₁₀N₂O 
• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 1122-62-9 2-acetylpyridine 
• 4744-02-9 1,3-di-(2'-pyridyl)-2-propen-1-one 

Relevant articles and documents

{Ru(CO)x}-core terpyridine complexes: Lysozyme binding affinity, DNA and photoinduced carbon monoxide releasing properties

Reaction of 4′-(2-pyridyl)-2,2′:6′,2″-terpyridine (LPY) and 4′-(4-phenylmorpholine)-2,2′:6′,2″-terpyridine (Lmorph) with {[RuCl2(CO)3]}2 in methanol affords [RuCl2(LPY-κ2N1N2)(CO)2] (1) and a mixture of [RuCl2(Lmoph-κ2N1N2)(CO)2]/[RuCl2(Lmorph-κ3N1N2N3)(CO)] (2), respectively. Their photoactivatable CO releasing properties are investigated upon the exposure to light source at 365 nm. One CO molecule is released from 1 at the excitation wavelength 365 nm, while the ligand changes its bidentate mode into the meridional tridentate one. The illumination profile and the influence of the uncoordinated pyridine arm on CO release are examined by solution 1H and 13C NMR spectroscopy. The electronic transitions are studied by TDDFT. The DNA and hen white egg lysozyme binding affinity of the complexes are studied by UV/Vis. and electrospray ionization mass spectrometry. Stable lysozyme complexes, capable of photo induce CO, are formed via the loss of the labile chloride ligands or terpyridine moiety.

Evaluation of DNA/Protein interactions and cytotoxic studies of copper(II) complexes incorporated with N, N donor ligands and terpyridine ligand

A series of four new copper(II) heteroleptic complexes, [Cu(2?-pytpy) (L)] (NO3)2·2H2O (1–4), where 2?-pytpy?=?4′-(2′′′-Pyridyl)-2, 2′:6′, 2′′-terpyridine, L?=?bipyridyl (bpy), 1, 10 phenanthroline(phen), dipyridoquinoxaline(dpq) and dipyridophenazine (dppz) were synthesized and characterized by spectroscopic techniques. Further, the molecular structure of the complex (2) was confirmed by single crystal X-ray diffraction technique and the data revealed a penta coordinated, distorted square-pyramidal geometry with triclinic system. The interactions of four complexes with calf thymus DNA and bovine serum albumin (BSA) were investigated by electronic absorption, fluorescence and circular dichroism spectroscopy techniques. Spectral studies substantiated an intercalative binding mode of metal complexes with ct-DNA. Significant binding interactions of the complexes with protein have been further revealed from fluorescence studies. Furthermore, all the four complexes show potential cytotoxicity towards the human liver carcinoma cell line (HepG-2).

Terpyridine Zn(II) azide compounds: Spectroscopic and DFT calculations

Square-pyramidal Zn(II) azide complexes with the formula of [Znn(N3)2nL] (n = 1; L = 4′-(2-pyridyl)-2,2′:6′,2′'-terpyridine (LPy), 4′-(4-phenylmorpholine)-2,2′:6′,2′'-terpyridine (LMorph), and n = 2; L = 1,4-bis(2,2′:6′,2′'-terpyridin-4′-yl)benzene (LBPY)) were synthesized, and structurally characterized using different spectroscopic and analytical tools. Ground-state geometry optimization and harmonic vibrational analysis were carried out at two different levels of theory (B3LYP/LANL2DZ and CAM-B3LYP/def2-SVP) to gather insights into the local minimum structures. Natural bond orbital (NBO) analyses revealed that the electronic population of the 3d orbitals of Zn(II) ion is corresponding to the oxidation state of Zn(I), not Zn(II), in agreement with the ligand to metal charge transfer. Molecular electrostatic potential energy maps showed that the azido ligand may act as a nucleophile in the cycloaddition coupling with electron poor dipolar molecules. The electronic structure and transitions were investigated by executing time dependent density functional theory (TDDFT) calculations.

Kinetically labile ruthenium(ii) complexes of terpyridines and saccharin: effect of substituents on photoactivity, solvation kinetics, and photocytotoxicity

Herein, we designed six kinetically labile ruthenium(ii) complexes containing saccharin (sac) and 4′-substituted-2,2′:6′,2′′-terpyridines (R-tpy),viz. trans-[Ru(sac)2(H2O)3(dmso-S)] (1) and [RuII(R-tpy)(sac)2(X)] [X = solvent molecule] (2-6). We intentionally kept the labile hydrolysable Ru-X bonds that were potentially activatedviasolvent-exchange reactions. This strategy generates a coordinative vacancy that allows further binding with potential biological targets. To gain insight into the electronic effects of ancillary ligands on Ru-X ligand-exchange kinetics or photoreactions, we have used a series of substituted terpyridines (R-tpy) and studied their solvation kinetics. The ternary complexes were also studied for their potential utility in Ru-assisted photoactivated chemotherapy (PACT) synergized with release of saccharin as a highly selective carbonic anhydrase IX (CA-IX) inhibitor, over-expressed in hypoxic tumors. The ternary complexes exhibit distorted octahedral geometry around Ru(ii) from two monodentatetransoidalsaccharin in the axial position, and tridentate terpyridines and labile solvent molecules at the basal plane (2-6). We studied their speciation, solvation kinetics, and photoreactivity in the presence of green LED light (λirr= 530 nm). All the complexes are relatively labile and undergo solvation in coordinating solvents (e.g.DMSO/DMF). The complexes undergo the ligand-substitution reaction, and their speciation and kinetics were studied by UV-Vis, ESI-MS,1H-NMR, and structural analysis. We also attempted to assess the effect of various substituents on the ancillary terpyridine ligand (R-tpy) in photo-reactivity and ligand-exchange reactions. The photo-induced absorption and emission measurements suggested dissociation of the saccharin from the Ru-center supporting PACT pathways. The complexes display a significant binding affinity with CT-DNA (Kb～ 104-105M?1) and bovine serum albumin (BSA) (KBSA～ 105M?1). Cytotoxicity was studied in the dark and the presence of low energy UV-A light (365 nm) in cervical cancer cells (HeLa) and breast cancer cells (MCF7). Photoirradiation of the complexes induces the generation of reactive oxygen species (ROS) assessed using 1,3-diphenylisobenzofuran (DPBF) and intracellular DCFDA assays. The complexes are sufficiently internalized in cancer cells throughout the cytoplasm and nucleus and induce apoptosis as studied by staining with dual dyes using confocal microscopy.

Case Study of the Correlation between Metallogelation Ability and Crystal Packing

In the present paper, in order to find the correlation between the molecular structure and the intermolecular interaction patterns in the crystalline state and the corresponding gelating or nongelating behavior, two structurally related sets of copper complexes, including (CuCl2[LTerpy2py]), 1, (CuCl2[LTerpy3py]), 2, and (CuCl2[LTerpy4py]), 3, (where LTerpynpy is 4′-(n-pyridyl)-2,2′,6′,2″-terpyridine) as the first set and (CuCl2[Ldipyz-py2py]), 4, (CuCl2[Ldipyz-py3py]), 5, and (CuCl2[Ldipyz-py4py]), 6, (where Ldipyz-pynpy is 4-(n-pyridyl)-2,6-dipyrazin-2-yl-pyridine) as the second one, have been synthesized, and their crystal packing as well as gelating properties have been investigated. Results show that although these two sets are structurally similar the first set forms a metastable hydrogel, while the second one is unable to form a gel. To investigate the reasons, we employed Hirshfeld surface analysis and examined the differences in their packing arrangements, which suggest hydrogen bonding arranged into the three-dimensional network is a preferred mode of packing for the crystalline solid but is unfavorable for gel formation.

Transition-Metal-Free Oxidative C(sp2)?H Hydroxylation of Terpyridines: A HOMO-Raising Strategy for the Construction of a New Super-Stable Terpyridine Chromophores

Direct functionalization of terpyridines is an increasingly important topic in the field of dyes and catalysis as well as supramolecular chemistry, but its synthesis and transformation is usually challenging. Herein, a HOMO-raising strategy is reported for the construction of a super-stable novel terpyridine chromophores, in which the selective oxidation of terpyridines at its 3-position was determined successfully to the synthesis of phenol-functionalization of terpyridines (TPyOHs) bearing a hydrogen bonding group. The corresponding TPyOHs displayed strong aggregation-induced emission and exhibited highly selective and visual detection of ZnII cation with a record green terpyridine-based luminophore with nanomolar sensitivity (125 nm).

Tuning the photophysical properties of 4′-substituted terpyridines - An experimental and theoretical study

Several 2,2′:6′,2″-terpyridines substituted in the 4′-position were synthesized and their photophysical properties were investigated by absorption and photoluminescence spectroscopy in dilute solutions and solid state. The studies confirmed that the absor

In situ selective N-alkylation of pendant pyridyl functionality in mixed-valence copper complexes with methanol and copper(ii) bromide

The reactions of CuBr2 with pyridyl 2,2′:6′, 2′′-terpyridine ligands in methanol yielded four copper complexes under solvothermal conditions. The self-assembly processes were accompanied by designing bitopic precursor ligands and increasing the stoichiometric metal-ligand ratio. In the four resulting complexes, the pendant pyridyl groups of pyridylterpyridine were selectively in situ N-methylated and yielded the 4′-(N-methylpyridinium)-2,2′:6′,2′′-terpyridine cations, including the 2-position pyridyl group which is difficult to be N-alkylated due to the steric problem. Partial divalent copper atoms were reduced to cuprous ones in the solvothermal reactions, which made the mixed-valence copper atoms coexist in each compound. The mixed-valence complexes have a varied dimensionality (from 2D to 0D) and the CuIBr cluster, which can be controlled by changing the metal-ligand ratio. Theoretical studies show that the nucleophilic attack of the nitrogen atom in the pendant pyridyl is more facile than others of terpyridine. A possible mechanism was also proposed. The Royal Society of Chemistry 2012.

DNA interaction, in vitro antimicrobial and SOD-like activity of copper(II) complexes with norfloxacin and terpyridines

The novel octahedral copper(II) complexes with the second generation fluoroquinolone, norfloxacin and terpyridine derivatives were prepared and characterized. The antimicrobial efficiency of the complexes were tested on five different microorganisms and s

Interactions with herring sperm DNA and biological studies of sparfloxacin drug-based copper(II) compounds

Copper(II) complexes of the type [Cu(SPF)(Ln)Cl] (where SPF is sparfloxacin and Ln = substituted terpyridines) were synthesized and found to have a distorted octahedral geometry. Superoxide dismutase-like activity of the complexes wa