129077-51-6

Basic information

• Product Name: 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE
• Synonyms: 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE
• CAS NO: 129077-51-6
• Molecular Formula: C₂₁H₁₄N₄O₂
• Molecular Weight: 354.36
• Mol File: 129077-51-6.mol

Chemical Properties

• Melting Point: 158-159 °C(Solv: ethanol (64-17-5))
• Boiling Point: 536.1 °C at 760 mmHg
• Flash Point: 278 °C
• Appearance: /
• Density: 1.28 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.41±0.22(Predicted)
• CAS DataBase Reference: 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE(129077-51-6)
• EPA Substance Registry System: 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE(129077-51-6)

Safety Data

• Hazardous Substances Data: 129077-51-6(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE is used as a ligand in coordination chemistry for its ability to form stable complexes with various metal ions. Its unique electronic properties make it suitable for studying metal coordination and investigating the structure and properties of metal complexes.
Used in Material Science:
In material science, 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE is used as a building block for the development of new materials with specific properties. Its photophysical characteristics allow it to be incorporated into materials that exhibit unique optical, electronic, or magnetic behaviors.
Used in Luminescent Materials:
4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE is used as a component in the design and synthesis of luminescent materials. Its photophysical properties contribute to the development of materials that emit light under certain conditions, which can be applied in various technologies such as lighting, displays, and sensors.
Used in Sensors:
4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE is utilized in the development of sensors due to its ability to interact with specific analytes and produce a measurable response. Its unique electronic properties make it a promising candidate for the creation of highly sensitive and selective sensors for various applications.
Used in Supramolecular Assemblies:
4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE is used as a building block for supramolecular assemblies, where non-covalent interactions lead to the formation of complex structures with unique properties. Its role in these assemblies contributes to the advancement of supramolecular chemistry and the development of new functional materials.

Upstream product

• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 18451-69-9 (2E)-3-(4-nitrophenyl)-1-(pyridin-2-yl)prop-2-en-1-one 
• 636-98-6 p-nitrobenzene iodide 
• 134653-69-3 4'-{[(Trifluoromethyl)sulfonyl]oxy}-2,2':6',2''-terpyridine 
• 149817-62-9 4'-bromo-2,2':6',2''-terpyridine 
• 381218-94-6 4'-((neopentyl glycolato)boron)-2,2':6',2''-terpyridine 
• 502622-85-7 5,5-dimethyl-2-(4-nitrophenyl)-1,3,2-dioxaborinane 
• 1122-62-9 2-acetylpyridine 
• 555-16-8 4-nitrobenzaldehdye 
• 1121-60-4 pyridine-2-carbaldehyde 

Downstream Products

• 1073314-51-8 4'-(N-(4-(2,4-dioxopentan-3-yl)phenyl)benamide)2,2':6',2''-terpyridine 
• 870814-19-0 [Ir(4-ethylbenzoate)3(4'-(phenyl-p-nitro)-2,2':6',2''-terpyridine)] 
• 1309474-97-2 (C₅H₄N)2C₅H₂NC₆H₄NHCOCH₂CH₂C₄NH(CH₃)(COOH)CONHC(NH₂)2⁽¹⁺⁾*Cl^(1-)=[C₃₂H₂₉N₈O₄]Cl 
• 1135134-65-4 (C₅H₄N)2(C₅H₂N)C₆H₄NHC(O)CH₂CH₂(C₄NH)(CH₃)(C(O)OH)C(O)NHC(NH)NH₂ 
• 870814-15-6 [Ru(4'-(phenyl-p-nitro)-2,2':6',2''-terpyridine)(CF₃CO₂)3] 

Relevant articles and documents

Optimising the synthesis, polymer membrane encapsulation and photoreduction performance of Ru(II)- and Ir(III)-bis(terpyridine) cytochrome c bioconjugates

Ruthenium(ii) and iridium(iii) bis(terpyridine) complexes were prepared with maleimide functionalities in order to site-specifically modify yeast iso-1 cytochrome c possessing a single cysteine residue available for modification (CYS102). Single X-ray crystal structures were solved for aniline and maleimide Ru(ii) 3 and Ru(ii) 4, respectively, providing detailed structural detail of the complexes. Light-activated bioconjugates prepared from Ru(ii) 4 in the presence of tris(2-carboxyethyl)-phosphine (TCEP) significantly improved yields from 6% to 27%. Photoinduced electron transfer studies of Ru(ii)-cyt c in bulk solution and polymer membrane encapsulated specimens were performed using EDTA as a sacrificial electron donor. It was found that membrane encapsulation of Ru(ii)-cyt c in PS140-b-PAA48 resulted in a quantum efficiency of 1.1 ± 0.3 × 10-3, which was a two-fold increase relative to the bulk. Moreover, Ir(iii)-cyt c bioconjugates showed a quantum efficiency of 3.8 ± 1.9 × 10-1, equivalent to a ～640-fold increase relative to bulk Ru(ii)-cyt c.

Self-assembly and photo-responsive behavior of bis-terpyridyl Eu3+-complex L1

In the present paper, a bis-terpyridyl Eu3+ complex (bis-terpyridyl Eu3+-complex L1) was synthesized through the coordination between Eu3+ and a compound L1 with an azobenzene-functionalized chain between the two terpyridi

Facile synthesis and photochromic properties of diarylethene-containing terpyridine and its transition metal (Zn2+/Co2+/Ru 2+) complexes

Several transition metal complexes based on 2,3-bis(2,4,5-trimethyl-3- thienyl)maleic anhydride (DTE) bearing terpyridine (TPY) have been designed and synthesized. Furthermore, the photochromism of the free ligand and the influence of transition metal moi

A novel bis(terpyridine) with π?conjugated phenyl viologen and its metallo- supramolecular polymers: Synthesis and electrochromism

A novel phenylene viologen functionalized bis(terpyridine) is synthesized and characterized with 1HNMR and Maldi-tof-MS. This rod-like and π-conjugated molecule, 1,1'-[4'-(4-phenyl)-2,2:6′,2″- terpyridine-4,4′-bipyridine-1,1′-diium dichloride (

Aggregation induced emission (AIE) active 4-amino-1,8-naphthalimide-Tr?ger's base for the selective sensing of chemical explosives in competitive aqueous media

The 4-amino-1,8-naphthalimide-Tr?ger's base fluorophore, TBNap-TPy, adorned with phenyl-terpyridine moiety was synthesised and assessed for its aggregation-induced emission (AIE) behaviour. TBNap-TPy was further employed as a fluorescent sensor for the di

Luminescent lanthanide(III) complexes of DTPA-bis(amido-phenyl-terpyridine) for bioimaging and phototherapeutic applications

We report here a series of coordinatively-saturated and thermodynamically stable luminescent [Ln(dtntp)(H2O)] [Ln(III) = Eu (1), Tb (2), Gd (3), Sm (4) and Dy (5)] complexes using an aminophenyl-terpyridine appended-DTPA (dtntp) chelating ligand as cell imaging and photocytotoxic agents. The N,N″-bisamide derivative of H5DTPA named as dtntp is based on 4′-(4-aminophenyl)-2,2′:6′,2″-terpyridine conjugated to diethylenetriamine-N,N′,N″-pentaacetic acid. The structure, physicochemical properties, detailed photophysical aspects, interaction with DNA and serum proteins, and photocytotoxicity were studied. The intrinsic luminescence of Eu(III) and Tb(III) complexes due to f → f transitions used to evaluate their cellular uptake and distribution in cancer cells. The solid-state structure of [Eu(dtntp)(DMF)] (1·DMF) shows a discrete mononuclear molecule with nine-coordinated {EuN3O6} distorted tricapped-trigonal prism (TTP) coordination geometry around the Eu(III). The {EuN3O6} core results from three nitrogen atoms and three carboxylate oxygen atoms, and two carbonyl oxygen atoms of the amide groups of dtntp ligand. The ninth coordination site is occupied by an oxygen atom of DMF as a solvent from crystallization. The designed probes have two aromatic pendant phenyl-terpyridine (Ph-tpy) moieties as photo-sensitizing antennae to impart the desirable optical properties for cellular imaging and photocytotoxicity. The photostability, coordinative saturation, and energetically rightly poised triplet states of dtntp ligand allow the efficient energy transfer (ET) from Ph-tpy to the emissive excited states of the Eu(III)/Tb(III), makes them luminescent cellular imaging probes. The Ln(III) complexes show significant binding tendency to DNA (K ~ 104 M?1), and serum proteins (BSA and HSA) (K ~ 105 M?1). The luminescent Eu(III) (1) and Tb(III) (2) complexes were utilized for cellular internalization and cytotoxicity studies due to their optimal photophysical properties. The cellular uptake studies using fluorescence imaging displayed intracellular (cytosolic and nuclear) localization in cancer cells. The complexes 1 and 2 displayed significant photocytotoxicity in HeLa cells. These results offer a modular design strategy with further scope to utilize appended N,N,N-donor tpy moiety for developing light-responsive luminescent Ln(III) bioprobes for theranostic applications.

Palladium supported terpyridine modified magnetic nanoparticles as an efficient catalyst for carbon-carbon bond formation

In this paper, a novel catalyst is designed, synthesized and characterized based on the functionalization of magnetic iron oxide nanoparticles by terpyridine as a ligand for the immobilization of palladium. The catalyst is fully characterized by several c

Phenyl-substituted 2,2′:6′,2″-terpyridine as a new series of fluorescent compounds - Their photophysical properties and fluorescence tuning

Several phenyl-substituted 2,2′:6′,2″-terpyridines (tpy) were synthesized and it was found that 4′-phenyl tpy (ptp, 3) exhibited the most effective fluorescence, whose quantum yield was up to 0.64 in cyclohexane. For further study on tuning the fluorescence properties of ptp, different substituents were introduced into the p-position of the phenyl group. While Br- 10, Cl- 11, and CH3-ptp 12 showed their absorption and fluorescence in the same region as 3, those of NH2- 14 and Me2N-ptp 15 were observed at much longer wavelengths. In addition, fluorescence maxima of 14 and 15 showed large (> 130 nm) solvent dependence. The difference between ground and excited state dipole moment (Δμ) for 15 was estimated to be 15.2 D by the Lippert-Mataga equation, indicating the intramolecular charge transfer (ICT) process. Semi-empirical MO calculation (MOPAC/AM1) demonstrated that the HOMO-1, HOMO and LUMO of 3, 10-12 were mainly localized on the phenyl (πph), tpy (πtpy) and tpy (π*tpy) part, respectively, indicating that the lowest energy absorption band of 3, 10-12 was the local excitation (πtpy-π*tpy). In the case of 14 and 15, which have an electron-donating substituent, πph instead of πtpy became the HOMO. Thus, the lowest energy absorption of 14 and 15 was an ICT transition (πph-π*tpy), and a large red shift of the fluorescence occurred. In these compounds, the energy level of πph is controlled without affecting that of πtpy and π*tpy, suggesting a novel approach for tuning the color of fluorescence.

Surface bottom-up fabrication of porphyrin-terminated metal complex molecular wires with photo-electron conversion properties on ITO

We fabricated photoelectron conversion system with porphyrin-terminated "molecular wires" on an ITO surface synthesized using stepwise metal-terpyridine complexation reactions. The efficiency and the electrode potential singniflcantly depended on the meta

2-(2′-Hydroxyphenyl)-benzothiazole (HBT)-terpyridine conjugate: A highly specific ICT based fluorescent probe for Zn2+ ions and its application in confocal cell imaging

A new fluorescent sensor based on benzothiazole-terpyridine conjugate is reported. It functions as a fluorescent sensor that is highly selective for the Zn2+ ions via internal charge transfer (ICT) mechanism in DMSO: H2O medium. The