163087-28-3

Usage

Uses

Used in Organic Light-Emitting Diodes (OLEDs):
2,2':6',2''-Terpyridine, 4'-(9-anthracenyl)is used as a luminescent material in OLEDs for its ability to emit light upon electrical stimulation. Its fluorescence and phosphorescence properties contribute to the efficient light emission and improved performance of these devices.
Used in Organic Photovoltaics (OPVs):
In the field of organic photovoltaics, 2,2':6',2''-Terpyridine, 4'-(9-anthracenyl)is employed as a component in the active layer of the solar cells. Its photophysical properties aid in the absorption of light and the generation of charge carriers, which are crucial for the conversion of solar energy into electricity.
Used in Supramolecular Assemblies:
2,2':6',2''-Terpyridine, 4'-(9-anthracenyl)is used as a building block in supramolecular chemistry for its ability to form non-covalent interactions with other molecules. This allows for the construction of complex molecular structures and materials with tailored properties.
Used in Coordination Chemistry:
As a versatile ligand, 2,2':6',2''-Terpyridine, 4'-(9-anthracenyl)is used in coordination chemistry to form coordination complexes with transition metal ions. These complexes can exhibit a range of interesting properties, such as catalytic activity, magnetic behavior, or optical properties, making them valuable for various applications in materials science and catalysis.

Upstream product

• 1122-62-9 2-acetylpyridine 
• 642-31-9 9-anthracene aldehyde 
• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 477566-79-3 (E)-3-(anthracen-9-yl)-1-(pyridin-2-yl)prop-2-en-1-one 

Relevant academic research and scientific papers

Twisted aromatics, 9-anthryl and 1-pyrenyl terpyridines organize into novel multi-directional 'ladder-like' motifs in the solid state

9-Anthryl and 1-pyrenyl terpyridines (1 and 2, respectively), key precursors for the design of novel fluorescent sensors have been synthesized and characterized by 1H NMR, mass spectroscopy and X-ray crystallography. Twisted molecular conformat

Insight into structure-property relationships of aryl-substituted 2,2′:6′,2″-terpyridines

A series of 2,2′:6′,2″-terpyridines functionalized with polyaromatic groups have been synthesized and their optical properties have been examined in detail, with the support of theoretical calculations at DFT/TD-DFT level. The investigated molecules show twisted ground state conformations with the twist angle impacted by steric hindrance due to the inter-ring H?H repulsions. The largest steric hindrance effect (77.3°) was found for 4′-(anthracen-9-yl)-2,2′:6′,2″-terpyridine, while replacement of 1-naphtyl, 9-anthryl and 1-pyrenyl with appropriate 2-naphtyl, 2-anthryl and 2-triphenylenyl results in the decrease in dihedral angle between the plane of polyaromatic group and central pyridine ring. The longest wavelength absorption band of anthryl-, pyrenyl- and perylenyl-substituted terpyridines is predominately contributed by the aryl unit, while low-energy absorptions of other Ar-terpys are assigned to both π?π*(terpy) and π?π*(aryl) transitions. For 4′-(pyren-1-yl)-2,2′:6′,2″-terpyridine and 4′-(perylen-3-yl)-2,2′:6′,2″-terpyridine, the UV–Vis spectra support relatively strong interaction between the chromophoric moieties of Ar-terpys in the ground state. In the excited singlet state, intramolecular charge transfer (ICT) transitions originating from charge delocalization from the aryl unit to terpy acceptor moiety has been evidenced for 4′-(anthracen-2-yl)-2,2′:6′,2″-terpyridine, 4′-(pyren-1-yl)-2,2′:6′,2″-terpyridine and 4′-(perylen-3-yl)-2,2′:6′,2″-terpyridine.

Synthesis, characterization, plasmid cleavage and cytotoxicity of cancer cells by a copper(ii) complex of anthracenyl-terpyridine

Metallo-organic compounds are interesting to study for their antitumor activity and related applications. This paper deals with the syntheses, characterization, structure determination of a copper complex of anthracenyl terpyridine (1) and its plasmid cleavage and cytotoxicity towards different cancer cell lines. The complex binds CT-DNA through partial intercalation mode. The plasmid cleavage studies carried out using pBR322 and pUC18 resulted in the formation of all the three forms of the plasmid DNA. Plasmid cleavage studies carried out with a non-redoxable Zn2+ complex (2) supported the role of the redox activity of copper in 1. The complex 1 showed remarkable antiproliferative activity against cancer cell lines, viz., cervical (HeLa, SiHa, CaSki), breast (MCF-7), liver (HepG2) and lung (H1299). A considerable lowering was observed in the IC50 values of HPV-infected (viz., HeLa, SiHa, CaSki) vs. non-HPV-infected cell lines (MCF-7, HepG2, H1299). Antiproliferative activity of 1 was found to be much higher than the carboplatin when treated with the same cell lines. Incubation of the cells with 1 results in granular structures only with the HPV-infected cells and not with others as studied by phase contrast and fluorescence microscopy. The lower IC50 value observed in case of 1 with HPV-infected cell lines may be correlated with the involvement of HPV oncoprotein. The role of HPV has been further augmented by transfecting the MCF-7 cells (originally not possessing HPV copy) with e6 oncoprotein cDNA. To our knowledge this is the first copper complex that causes cell death by interacting with HPV oncoprotein followed by exhibition of remarkable antiproliferative activity.

Cd(ii)-terpyridine-based complex as a ratiometric fluorescent probe for pyrophosphate detection in solution and as an imaging agent in living cells

The terpyridine anthracene ligand L1 was synthesized and characterized. L1 is a ratiometric fluorescent probe for Cd2+ with a recognition mechanism based on intramolecular charge transfer (ICT). An L1-Cd(ii) complex was isolated, and its structure was established using single-crystal XRD. The L1-Cd(ii) complex was able to serve as a novel reversible chemosensing ensemble to allow ratiometric response to pyrophosphate (PPi) in aqueous media. Moreover, the fluorescence imaging in living cells from these two emission channels suggested that L1 was a ratiometric probe for Cd2+, and the in situ generated L1-Cd(ii) complex was also a ratiometric ensemble for PPi detection in living cells. This journal is

A Highly Selective and Efficient Copper(II) – “Turn-On” Fluorescence Imaging Probe for l-Cysteine

A simple copper(II) complex of the anthracenyl-appended terpyridine ligand 4′-(anthracen-9-yl)-2,2′:6′,2′′-terpyridine (L), [Cu(L)Cl2] (1, ESI-MS, m/z = 507.08), is reported as a highly selective “turn-on” optical imaging probe for l-cysteine. Probe 1 shows a CuII/CuIredox potential [E1/2= –0.194 V versus normal hydrogen electrode (NHE)] within a biologically viable range. The copper center in 1 adopts a square-pyramidal geometry (τ = 0.0851), and the Cu–Npybond (1.970 ?) of the middle pyridine (py) ring is shorter than the other two Cu–Npybonds (2.069 and 2.040 ?). The Cu–Cl bonds (2.444 and 2.027 ?) are labile enough to be replaced by solvent molecules. The square-based geometry is further supported by the A∥value of 156.8 × 10–4cm–1determined by electron paramagnetic resonance (EPR) spectroscopy at 70 K. The d–d transition of 1 in acetonitrile/4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (acetonitrile/HEPES) buffer at pH 7.34 appears at λ =760 nm (ε = 198 m–1cm–1), and the ligand-based transitions are observed at λ = 327–384 nm. The ligand shows strong fluorescence at λ = 430 nm with a quantum yield of 11 %, but its emission intensity is completely quenched on coordination with Cu2+ions, as in 1. Probe 1 detects l-cysteine selectively through turn-on fluorescence intensity at λem= 431 nm with a limit of detection of 1.9 × 10–8m at pH 7.34. Interestingly, probe 1 is able to visualize exogenously added l-cysteine in Henrietta Lack cervical cancer (HeLa) cells, human liver hepatocellular carcinoma (HepG2) cells, and human embryonic kidney 293 (HEK293) cells under identical conditions at pH 7.4 in confocal microscopy imaging.

A new europium chelate-based phosphorescence probe specific for singlet oxygen

The first Eu3+ chelate-based phosphorescence probe specific for singlet oxygen has been designed, synthesized and characterized. The probe is highly sensitive, selective and water soluble for time-resolved luminescence detection of singlet oxygen with a detection limit of 2.8 nM. The Royal Society of Chemistry 2005.

Abrupt spin transition in a modified-terpyridine cobalt(ii) complex with a highly-distorted [CoN6] core

The cobalt(ii) complex incorporating π-conjugated substituent, [Co(Naph-C2-terpy)2](BF4)2 (1; Naph-C2-terpy = 4′-(2-naphthoxy(ethoxy))-2,2′:6′,2′′-terpyridine), exhibits an abrupt spin transition (ST) behavior (cooperative factor C = 0.91) while its solvated product, 1·2MeOH, shows gradual spin crossover (SCO) behavior (C = 0.49). Single crystal X-ray structural analyses demonstrated that the octahedral coordination core [CoN6] in 1 shows larger distortion in both high-spin and low-spin states than solvated 1·2MeOH or another two derivatives, [Co(R-terpy)2](BF4)2 (R = 2-naphthyl (2), 9-anthracenyl (3)). The respective distortion parameters (Σ) are compared with those for previously reported SCO cobalt(ii) compounds. The highly-distorted [CoN6] core in 1 (Σ = 126 in the HS state and 101.6 in the LS state) was stabilized by strong intermolecular interactions and observed an abrupt ST behaviour.

DNA interaction, free radical scavenging and in-vitro antibacterial activity of drug-based copper(II) complexes

The Cu(II) complexes of type [Cu(cpf)(An)Cl] (An = terpyridines, cpf = ciprofloxacin) were synthesized and characterized using IR, mass and reflectance spectra. The free ligands and their complexes were evaluated for their in-vitro antimicrobial activity against a panel of Gram-positive and Gram-negative bacteria. The complexes exhibit better or equal inhibition in comparison to free fluoroquinolones. Binding interactions of the complexes with calf thymus (CT DNA) were investigated by absorption titration, viscosity studies and DNA melting temperature experiment. The cleavage reaction on pUC19 DNA was monitored by agarose gel electrophoresis. The lower concentration of the complexes was catalysed the dismutation of superoxide radical at biological pH, which indicates that the complexes can act as a possible model for superoxide dismutase. Copyright

Cyclometalated Ir(III) Complexes Involving Functionalized Terpyridine-Based Ligands Exhibiting Aggregation-Induced Emission and Their Potential Applications in CO2 Detection

Synthesis of three novel terpyridine-based donor-acceptor (D-A) ligands (TP1, TP2, TP3) and cyclometalated iridium complexes [Ir(ppy)2TP1]+PF6- (C1), [Ir(ppy)2TP2]+PF6- (C2), and [Ir(ppy)2TP3]+PF6- (C3) [ppy = 2-phenyl pyridine] involving these were described. The ligands and complexes were characterized by spectroscopic studies (1H, 13C, 19F, 31P, ESI-MS, UV-vis, and fluorescence). Crucial role of intermolecular interactions in aggregation-caused quenching (ACQ; C2) and aggregation-induced emission (AIE; C3) was rationalized by X-ray single-crystal analyses. Vital role of restricted intramolecular rotation (RIR) in inducing AIE upon aggregation via π-π interactions in these complexes was scrutinized by various studies. Because of strong intramolecular charge transfer these D-A based AIEgens exhibited solvatochromism. Further, AIE property of the complexes C1 and C3 was exploited toward detection of CO2.

Synthesis and time-resolved fluorimetric application of a europium chelate-based phosphorescence probe specific for singlet oxygen

A new europium chelate, [4′-(9-anthryl)-2,2′:6′,2″- terpyridine-6,6″-diyl]bis(methylenenitrilo) tetrakis(acetate)-Eu 3+ (ATTA-Eu3+), has been designed and synthesized as a highly sensitive and selective time-resolved phosphorescence probe for singlet oxygen (1O2). The probe can specifically react with 1O2 to yield its endoperoxide (EP-ATTA-Eu3+) with a great increase of the luminescence quantum yield and a long phosphorescence lifetime of 1.21 ms, which renders the probe favorable to be used for highly sensitive time-resolved luminescence detection of 1O2. The new phosphorescence probe is highly water soluble with a large stability constant of ～1020 and a wide available pH range at pH > 3. Upon reactions with some reactive oxygen species including hydrogen peroxide, superoxide, hydroxyl radical and 1O2, the probe shows high specificity for 1O2. The probe was used for quantitative detection of 1O2 generated from a MoO42+-H2O2 system to give a detection limit of 2.8 nM. Furthermore, the good applicability of the probe was demonstrated by the real-time monitoring of the kinetic process of 1O2 generation in a horseradish peroxidase (HRP) catalyzed oxidation system of indole-3-acetic acid (IAA) in a weakly acidic buffer and in a photosensitization system of 5,10,15,20-tetrakis(N-methyl-4-pyridyl)-21H,23H- porphine (TMPyP) in a neutral buffer. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.