81998-04-1

Usage

Uses

Used in Coordination Chemistry:
4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl is used as a ligand for forming complexes with transition metal ions. Its unique structure allows for versatile coordination modes, which is crucial for the development of new materials with tailored properties.
Used in Metal-Organic Frameworks (MOFs):
In the field of MOFs, 4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl is utilized as a building block to create porous materials with high surface areas. These frameworks have potential applications in gas storage, separation, and catalysis due to their tunable pore sizes and functionalities.
Used in Catalysis:
4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl, when complexed with metal ions, can act as a catalyst in various chemical reactions. Its ability to stabilize metal centers and facilitate electron transfer makes it a promising candidate for catalytic applications.
Used in Sensor Development:
4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl's interaction with metal ions can be exploited in the development of sensors. Changes in the electronic properties upon metal ion binding can be transduced into measurable signals, making it useful for detecting specific ions or monitoring chemical reactions.
Used in Pharmaceutical Development:
4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl also holds potential in the medicinal field, particularly in the design and synthesis of pharmaceuticals. Its ability to chelate metal ions can be leveraged to develop drugs with improved bioavailability and therapeutic efficacy.
Used in Materials Science:
In materials science, 4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl can be incorporated into the design of advanced materials with specific optical, electronic, or magnetic properties. Its versatility in forming complexes makes it a valuable component in the development of functional materials for various applications.
Overall, 4-HydroxyMethyl-4'-Methyl-2,2'-bipyridyl is a versatile compound with applications spanning across coordination chemistry, materials science, catalysis, sensor development, and pharmaceuticals, making it a valuable asset in both academic research and industrial applications.

Upstream product

• 712-61-8 2,2'-dimethyl-4,4'-bipyridine 
• 81998-03-0 4,4’-dimethyl-2,2’-bipyridine N-oxide 
• 108-89-4 picoline 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 104704-09-8 4'-methyl-2,2'-bipyridine-4-carboxylaldehyde 

Downstream Products

• 96897-04-0 1,2-bis(4′-methyl-[2,2′-bipyridin]-4-yl)ethane 
• 81998-05-2 4-bromomethyl-4'-methyl-2,2'-bipyridine 
• 104704-09-8 4'-methyl-2,2'-bipyridine-4-carboxylaldehyde 

Relevant academic research and scientific papers

An efficient ruthenium tris(bipyridine)-based luminescent chemosensor for recognition of Cu(ii) and sulfide anion in water

A novel efficient luminescent chemosensor based on a 1,4,7,10- tetraazacyclododecane (cyclen)-tethered Ru(bpy)32+ derivative (Ru-cyclen) has been synthesized and characterized. It displays an ON-OFF-type luminescence change with excellent selectivity towards Cu(ii) amongst 16 metal ions in 100% aqueous solution. The binding stoichiometry of Ru-cyclen with Cu2+ was established by Job plot analysis and mass spectral evidence. Furthermore, the in situ generated Ru-cyclen-Cu ensemble recovered luminescence in the presence of S2-, indicating an 'OFF-ON'-type sensing process. Similar phenomena were not observed with other common anions and biothiols, making it a high selective sulfide probe. Finally, the sensing mechanism is confirmed to be displacement approach by NMR, mass and emission spectrometry.

Multi-stimuli Photo and Redox-active Nanostructured Mesoporous Silica Films on Transparent Electrodes

Silica matrices hosting transition metal guest complexes may offer remarkable platforms for the development of advanced functional devices. We report here the elaboration of ordered and vertically oriented mesoporous silica thin films containing covalently attached tris(bipyridine)iron derivatives using a combination of electrochemically assisted self-assembly (EASA) method and Huisgen cycloaddition reaction. Such a versatile approach is primarily used to bind nitrogen-based chelating ligands such as (4-[(2-propyn-1-yloxy)]4’-methyl-2,2’-bypiridine, bpy’) inside the nanochannels. Further derivatization of the bpy’-functionalized silica thin films is then achieved via a subsequent in-situ complexation step to generate [Fe(bpy)2(bpy’)]2+ inside the mesopore channels. After giving spectroscopic evidences for the presence of such complexes in the functionalized film, electrochemistry is used to transform the confined diamagnetic (S=0) (Formula presented.) species to paramagnetic (S=1/2) oxidized (Formula presented.) species in a reversible way, while blue light irradiation (λ=470 nm) enables populating the short-lived paramagnetic (S=2) (Formula presented.) excited state. [Fe(bpy)2(bpy’)]2+-functionalized ordered films are therefore both electro- and photo-active through the manipulation of the oxidation state and spin state of the confined complexes, paving the way for their integration in optoelectronic devices.

Mechanochemical Release of Non-Covalently Bound Guests from a Polymer-Decorated Supramolecular Cage

Supramolecular coordination cages show a wide range of useful properties including, but not limited to, complex molecular machine-like operations, confined space catalysis, and rich host–guest chemistries. Here we report the uptake and release of non-covalently encapsulated, pharmaceutically-active cargo from an octahedral Pd cage bearing polymer chains on each vertex. Six poly(ethylene glycol)-decorated bipyridine ligands are used to assemble an octahedral PdII6(TPT)4 cage. The supramolecular container encapsulates progesterone and ibuprofen within its hydrophobic nanocavity and is activated by shear force produced by ultrasonication in aqueous solution entailing complete cargo release upon rupture, as shown by NMR and GPC analyses.

Adjusting the lipid-water distribution coefficient of iridium(iii) complexes to enhance the cellular penetration and treatment efficacy to antagonize cisplatin resistance in cervical cancer

The effective design of metal complexes to manipulate their lipid-water distribution coefficient is an appealing strategy for improving their cellular penetration and treatment efficacy. Here, we conveniently synthesized three iridium (Ir) complexes with red fluorescence via the simple non-conjugate modification of the side arm of the ligand. Bio-evaluation revealed that upon adding non-conjugate selenium (Se) arene derivatives, the lipid-water distribution coefficient of Ir-Se was found to be suitable, not only decreasing the toxic side effects of complexes to normal cells, but also effectively improving their anticancer activity via enhancing their penetration into tumor cells. Moreover, mechanistic investigations demonstrated that Ir-Se entered R-HeLa cells through endocytosis, and triggered apoptosis via the down-regulation of the mitochondrial membrane potential and excessive production of singlet oxygen, thereby possessing a highly effective cytotoxicity to antagonize cisplatin resistance. Therefore, we developed a convenient strategy to derive functional metal complexes and revealed that the introduction of Se on the side arm of the ligand provided the complexes with the capacity to reverse multidrug resistance.

Light-Activated Electron Transfer and Turnover in Ru-Modified Aldehyde Deformylating Oxygenases

Conversion of biological molecules into fuels or other useful chemicals is an ongoing chemical challenge. One class of enzymes that has received attention for such applications is aldehyde deformylating oxygenase (ADO) enzymes. These enzymes convert aliphatic aldehydes to the alkanes and formate. In this work, we prepared and investigated ADO enzymes modified with RuII(tris-diimine) photosensitizers as a starting point for probing intramolecular electron transfer events. Three variants were prepared, with RuII-modification at the wild type (WT) residue C70, at the R62C site in one mutant ADO, and at both C62 and C70 in a second mutant ADO protein. The single-site modification of WT ADO at C70 using a cysteine-reactive label is an important observation and opens a way forward for new studies of electron flow, mechanism, and redox catalysis in ADO. These Ru-ADO constructs can perform the ADO catalytic cycle in the presence of light and a sacrificial reductant. In this work, the Ru photosensitizer serves as a tethered, artificial reductase that promotes turnover of aldehyde substrates with different carbon chain lengths. Peroxide side products were detected for shorter chain aldehydes, concomitant with less productive turnover. Analysis using semiclassical electron transfer theory supports proposals for hopping pathway for electron flow in WT ADO and in our new Ru-ADO proteins.

Cyclometalated Iridium(III) Bipyridine–Phenylboronic Acid Complexes as Bioimaging Reagents and Luminescent Probes for Sialic Acids

Sialic acids play important roles in mammalian development, cell–cell attachment, and signaling. As cancer cells utilize their overexpressed sialylated antigens to propagate metastases, the development of probes for sialic acids is of high importance. Herein, we report three luminescent cyclometalated iridium(III) bipyridine complexes bearing a phenylboronic acid (PBA) moiety. Spectrophotometric titrations revealed that the PBA complexes displayed higher binding affinity for the most common sialic acid N-acetylneuraminic acid (Neu5Ac) compared with simple sugars that are commonly found on glycoproteins. Notably, cellular imaging and uptake experiments showed that the PBA complexes were able to recognize cellular sialic acid residues, resulting in more efficient uptake than the boronic acid-free analogs. Additionally, one of the PBA complexes was shown to discriminate between cancerous and noncancerous cells.

Effect of ligand sequence-specific modification on DNA hybrid catalysis

Development of a stereoselective asymmetric catalytic system with high conversion is the key to success for acquiring chiral materials. In recent years, DNA hybrid catalysts have attracted significant interest due to their excellent abilities in accelerat

Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts

The use of noncovalent interactions to direct transition-metal catalysis is a potentially powerful yet relatively underexplored strategy, with most investigations thus far focusing on using hydrogen bonds as the controlling element. We have developed an ion pair-directed approach to controlling regioselectivity in the iridium-catalyzed borylation of two classes of aromatic quaternary ammonium salts, leading to versatile meta-borylated products. By examining a range of substituted substrates, this provides complex, functionalized aromatic scaffolds amenable to rapid diversification and more broadly demonstrates the viability of ion-pairing for control of regiochemistry in transition-metal catalysis.

Palladium metal nanoparticles stabilized by ionophilic ligands in ionic liquids: Synthesis and application in hydrogenation reactions

The reduction of [Pd(acac)(COD)]BF4 (acac = acetylacetonate; COD = 1,5-cyclooctadiene), dissolved in BMI·BF4, in the presence of P- or N-containing ionophilic ligands by H2 yields "soluble" and stable [Pd(0)]n nanoparticles (NPs). These ionic liquid soluble NPs are active and selective catalysts for the hydrogenation of 1,3-dienes and alkynes under mild reaction conditions. Selectivities up to 87% to cis-2-pentene and 95% conversion were obtained using Pd NPs modified with 1-(3-(diphenylphosphino)propyl)-2,3-dimethyl-1H-imidazol-3-ium N-bis(trifluoromethylsulfonyl)imide in 1-n-butyl-3-methylimidazolium tetrafluoroborate.

Artificial photosynthesis dendrimers integrating light-harvesting, electron delivery and hydrogen production

A series of artificial photosynthesis complexes, Gn-Ir-Hy (n = 1-4), were constructed by attaching iridium complexes and [Fe-Fe]-hydrogenase mimic to the periphery and core, respectively, of poly(aryl ether) dendrimers of different generations. The iridium complexes act as the light-harvesting antennae and the hydrogenase mimic core is the catalytic center. Light-harvesting, photoinduced electron-transfer, and hydrogen photochemical production were hierarchically realized within the dendritic photosynthesis mimics using triethylamine as the sacrificial electron donor. The catalytic activity is enhanced as the generation of dendritic catalysts increases, and the turnover number for generation 4 is nearly 4 times more than that of generation 1. The peripheral antennae not only harvest photons but also act as electronic energy reservoirs for the photochemical production, which facilitates the catalytic process together with the increased light-harvesting and protection effects of dendritic frameworks. Therefore, efficient artificial photosynthesis systems with complete light-harvesting and catalytic functions can be advanced with such rational design.