133308-61-9

Usage

Uses

Used in Pharmaceutical Industry:
4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride is used as a synthetic intermediate for the preparation of aminophenylporphyrins, which are important compounds in the pharmaceutical industry. These porphyrins have potential applications in the development of drugs targeting various diseases, including cancer, due to their unique chemical and photophysical properties.
Used in Chemical Research:
In the field of chemical research, 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride serves as a valuable building block for the synthesis of novel bipyridine-based compounds. These compounds can be further explored for their potential applications in various areas, such as materials science, catalysis, and medicinal chemistry.
Used in Material Science:
The compound can also be utilized in material science as a component in the development of new materials with specific properties, such as conductivity, magnetism, or optical activity. The unique structure of 4'-methyl-2,2'-bipyridinyl-4-carbonyl chloride allows for the creation of complex molecular architectures that can be tailored for specific applications.

Upstream product

• 103946-54-9 4'-methyl-2,2'-bipyridine-4-carboxylic acid 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 

Downstream Products

• 913341-45-4 bis(4'-methyl-2,2'-bipyridinyl-4-carboxamide)-N,N'-(1,4-phenylene) 
• 244004-92-0 5-[4-(4-methyl-2,2'-bipyridine-4'-carboxyamidyl)phenyl]-10,15,20-triphenylporphyrinatozinc(II) 
• 1065473-88-2 5-(4-(4-methyl-2,2'-bipyridine-4'-carboxyamidyl)phenyl)-10,15,20-triphenylporphyrinatopalladium(II) 
• 1393556-22-3 [Zn((C₅H₂N)4(C₆H₅)3)C₆H₄NHC(O)C₆H₃(OCH₃)NHC(O)(C₁₀H₆N₂CH₃)] 
• 1328942-20-6 4-methyl-2,2'-bipyridine-4'-CONH-3-(2-benzoimidazole)-L-tyrosine ethyl ester 
• 1328942-29-5 4-methyl-2,2'-bipyridine-4'-CONH-3-(pyrid-2'-yl)-L-tyrosine ethyl ester 
• 1328942-25-1 4-methyl-2,2'-bipyridine-4'-CONH-3-(2-methlylenebenzoimidazole)-O-allyl-L-tyrosine ethyl ester 
• 1065270-60-1 4-methyl-2,2'-bipyridine-4'-carboxyamidyl-4-(tert-butylphenyl) 
• 913341-46-5 bis(4'-methyl-2,2'-bipyridinyl-4-carboxamide)-N,N'-(4,4'-biphenylene) 
• 133308-60-8 4-methyl-2,2'-bipyridyl-N-(5-p-phenylene-10,15,20-tri-p-tolylporphyrin)-4'-amide 
• 1208003-60-4 C₂₈H₂₄N₆ 

Relevant academic research and scientific papers

Tris(rhenium fac-tricarbonyl) Polypyridine Functionalized Cyclotriguaiacylene Ligands with Rich and Varied Emission

Trinuclear rhenium fac-tricarbonyl bromide complexes have been synthesized coordinated to the host ligands tris(4-[4-methyl-2,2′-bipyridyl]methyl)cyclotriguaiacylene (L1), tris(4-[4-methyl-2,2′-bipyridoyl])cyclotriguaiacylene (L2), and tris(4-[2,2′,6′,2″-terpyridyl]benzyl)cyclotriguaiacylene (L3). The structure of L1 and complexes [{Re(CO)3Br}3(L1)] (1) and [{Re(CO)3Br}3(L3)] (3) have been elucidated through X-ray single-crystal diffraction, with complex 3 crystallizing as a conglomerate. The steady-state luminescent properties and time-resolved fluorescence studies of the complexes have been conducted and revealed an unusual dual-emission phenomenon for complex 2. Complexes 1 and 2 show red-shifted emission wavelengths in comparison with those typical of monometallic Re(CO)3-bipy-Br complexes, while complex 3 showed an unusual excitation-dependent variation of emission wavelength.

Synthesis, electrochemical, and photophysical studies of multicomponent systems based on porphyrin and ruthenium(II) polypyridine complexes

Two ruthenium tris-bipyridine functionalized porphyrins 4, 8 and their Zn derivatives 4-Zn, 8-Zn were designed, synthesized, and characterized. The redox potentials of these complexes as well as their corresponding monomeric reference porphyrin and ruthen

Metal-organic approach to binary optical memory

Two new Ru(II) diimine chromophores, each containing a single photochromic dianthryl unit, have been prepared and characterized. The photoluminescence from the Ru(II) complexes is modulated by the photochromic action of the dianthryl species, which serves as a triplet energy transfer quencher in one photochromic state. The coupling of the dianthryl photochromic action to the Ru(II) complex emission permits nondestructive photoluminescence readout of binary information photochemically recorded on the molecular level. Luminescent images stored on polystyrene films that contain these molecules maintained their integrity for periods of months with no apparent degradation or variation in the image resolution, suggesting their durability for long-term storage in read-only memory applications. Copyright

Photoinduced electron transfer in amino acid assemblies

The preparation and photophysical characterization of a of redox-active lysines and related model compounds based on polypyridyl ruthenium complexes are described. Donor-chromophore-acceptor triad 1, [PTZpn-Lys(RuIIb2m)2+-NH-prPQ2+] (PF6-)4 (see below), by of a bipyridyl caromophore (RuIIb2m, where b = 2,2′-bipyridine, m = 4′-methyl-2,2′-bipyridyl-4′-carbonyl), an electron donor (phenothiazine, PTZ), and an (paraquat, PQ2+) on a (Lys) scaffold utilizing bonds. This derivatized amiono acid exihibited efficient (>95%) quenching of the ruthenium metal-to-ligand charge-transfer (MLCT) excited state upon irradiation with a 420-nm laser pulse in CH3CN. The resulting state, [(PTZpn+)-Lys(RuIIb2m) 2+-NH-(prPQ+)]) 1.17 eV and lived for 108 ns (k = 9.26 × 106 s-1) as observed by transient absorption spectrosoopy. Also studied was a of related model systems that included model chroaophores, simple chromophore-quencher dyads linked by amide bonds, and chromophore-queneher dyads on lysine. An account of the of kinetic behavior of these system including triad 1 and a discussion of factors that influence the lifetime of the redox-separated states, their efficiency of formation, their energy storage ability are presented.

A novel ruthenium(II) tris(bipyridine)-zinc porphyrin-rhenium carbonyl triad: Synthesis and optical properties

A novel ruthenium(II) tris(bipyridine)-zinc porphyrin-rhenium carbonyl triads and its free base porphyrin derivative were synthesized and characterized by 1H, 13C NMR, UV-vis, mass-spectrometry and elemental analysis. The redox poten

Synthesis, characterization and some properties of amide-linked porphyrin-ruthenium(II) tris(bipyridine) complexes

A new molecular dyad, comprised of a zinc-porphyrin and a ruthenium(II) tris(bipyridine) complex linked through an amide bond has been synthesized and characterized by 1H, 13C NMR, UV-vis, mass-spectrometry and elemental analysis. The electrochemistry as well as the steady-state emission properties were investigated. The redox behavior of the dyad exhibits a favorable reversible characteristic. Substantial quenching of porphyrin emission was found when the Q band of 5 and 5-Zn was selectively photoexcited. This observation suggests a quenching mechanism with possible intramolecular electron transfer or energy transfer between the Ru(bpy)3 moiety and the porphyrin free-base or Zn porphyrin moieties.

Re(I) sensitised near-infrared lanthanide luminescence from a hetero-trinuclear Re2Ln array

The trinuclear complexes Re2Ln (Ln = Nd, Yb or Er) contain two ReI tricarbonyl units linked to a DTPA binding site via 2,2′-bipyridyl ligands; LnIII-centred emission is sensitised by the ReI MLCT excited states.

Synthesis, Characterization and Photochromic Studies of Spirooxazine-Containing 2,2′-Bipyridine Ligands and Their Rhenium(I) Tricarbonyl Complexes

A series of spirooxazine-containing 2,2′-bipyridine ligands and their rhenium(I) tricarbonyl complexes has been designed and synthesized, and their photophysical, photochromic and electrochemical properties have been studied. The X-ray crystal structures

Bioactive half-sandwich Rh and Ir bipyridyl complexes containing artemisinin

Reaction of dihydroartemisinin (DHA) with 4-methyl-4′-carboxy-2,2′-bipyridine yielded the new ester derivative L1. Six novel organometallic half-sandwich chlorido Rh(III) and Ir(III) complexes (1–6) containing pentamethylcyclopentadienyl, (Cp*), tetramethylphenylcyclopentadienyl (Cpxph), or tetramethylbiphenylcyclopentadienyl (Cpxbiph), and N,N-chelated bipyridyl group of L1, have been synthesized and characterized. The complexes were screened for inhibitory activity against the Plasmodium falciparum 3D7 (sensitive), Dd2 (multi-drug resistant) and NF54 late stage gametocytes (LSGNF54), the parasite strain Trichomonas vaginalis G3, as well as A2780 (human ovarian carcinoma), A549 (human alveolar adenocarcinoma), HCT116 (human colorectal carcinoma), MCF7 (human breast cancer) and PC3 (human prostate cancer) cancer cell lines. They show nanomolar antiplasmodial activity, outperforming chloroquine and artemisinin. Their activities were also comparable to dihydroartemisinin. As anticancer agents, several of the complexes showed high inhibitory effects, with Ir(III) complex 3, containing the tetramethylbiphenylcyclopentadienyl ligand, having similar IC50 values (concentration for 50% of maximum inhibition of cell growth) as the clinical drug cisplatin (1.06–9.23 μM versus 0.24–7.2 μM, respectively). Overall, the iridium complexes (1–3) are more potent compared to the rhodium derivatives (4–6), and complex 3 emerges as the most promising candidate for future studies.

Synthesis, Characterization, and Photochromic Studies of Cyclometalated Iridium(III) Complexes Containing a Spironaphthoxazine Moiety

A series of cyclometalated iridium(III) complexes has been designed and synthesized, and their photophysical, photochromic, and electrochemical properties have been studied. The X-ray crystal structure of complex 2 has been determined. The emission properties of the complexes have been shown to be readily perturbed through the modification of the electronic properties of the phenylpyridine ligand. With different substituents at the phenylpyridine ligand of iridium(III) complexes of 1 (-H), 2 (-OMe), 3 (-CHO), and 4 (-CF3), they can display intense 3MLCT [dπ(Ir) → π*(diimine)] luminescence from 530 to 640 nm to span across the green to orange region. The spectral assignment is also in agreement with the electrochemical studies and DFT calculations. In addition, the photochromic behavior can be easily modulated by varying the substituents on the C∧N ligand without the need for tedious modification of the spirooxazine framework. By analyzing the kinetic profiles of backward bleaching reactions, less electron-rich iridium(III) complexes can stabilize the merocyanine form with a higher activation barrier. The studies have provided not only fundamental understanding on structure-property relationships that govern the versatile luminescence behavior of these Ir(III) complexes but also the guiding principles in the molecular design for the future developments of visible light-driven photoswitches.