20588-62-9

Usage

Uses

Used in Organic Synthesis:
3-Methoxy triphenylamine 97 is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Its aromatic structure and methoxy group make it a valuable building block for the development of new molecules with potential applications in various industries.
Used in the Synthesis of Schiff Base Molecules:
3-Methoxy triphenylamine 97 is used as a starting material in the synthesis of Schiff base molecules. Schiff bases are a class of compounds formed by the condensation of amines with aldehydes or ketones, and they exhibit a wide range of biological and chemical properties.
Used as Fluorescence and Colorimetric Chemosensors:
3-Methoxy triphenylamine 97-based Schiff base molecules can be used as fluorescence and colorimetric chemosensors to selectively detect zinc(II) and cadmium(II) ions in acetonitrile/aqueous solutions. These chemosensors have potential applications in environmental monitoring, industrial processes, and medical diagnostics, as they can provide sensitive and selective detection of metal ions, which are often toxic and can have detrimental effects on human health and the environment.

InChI:InChI=1/C19H17NO/c1-21-19-14-8-13-18(15-19)20(16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2-15H,1H3

Upstream product

• 591-50-4 iodobenzene 
• 536-90-3 m-Anisidine 
• 12775-96-1 copper 
• 108-86-1 bromobenzene 
• 101-16-6 3-methoxy-N-phenylaniline 
• 2398-37-0 3-methoxyphenyl bromide 
• 90-04-0 2-methoxy-phenylamine 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 122-39-4 diphenylamine 
• 766-85-8 3-methoxy-1-iodobenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 107396-23-6 N-(3-hydroxyphenyl)-diphenylamine 
• 42481-46-9 o-Methoxy-p-diphenylaminobenzylidenmalonitril 

Relevant academic research and scientific papers

Biaryl Phosphine Based Pd(II) Amido Complexes: The Effect of Ligand Structure on Reductive Elimination

Kinetic studies conducted under both catalytic and stoichiometric conditions were employed to investigate the reductive elimination of RuPhos (2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl) based palladium amido complexes. These complexes were found to be the resting state in Pd-catalyzed cross-coupling reactions for a range of aryl halides and diarylamines. Hammett plots demonstrated that Pd(II) amido complexes derived from electron-deficient aryl halides or electron-rich diarylamines undergo faster rates of reductive elimination. A Hammett study employing SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) and analogues of SPhos demonstrated that electron donation of the lower aryl group is key to the stability of the amido complex with respect to reductive elimination. The rate of reductive elimination of an amido complex based on a BrettPhos-RuPhos hybrid ligand (2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,6′-diisopropoxybiphenyl) demonstrated that the presence of the 3-methoxy substituent on the "upper" ring of the ligand slows the rate of reductive elimination. These studies indicate that reductive elimination occurs readily for more nucleophilic amines such as N-alkyl anilines, N,N-dialkyl amines, and primary aliphatic amines using this class of ligands.

Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules

Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.

Rational design of coumarin fluorophore with solvatochromism, AIE and mechanofluorochromic enhancement properties

A new fluorophore 7-(diphenylamino)coumarin-4-yl pivalate (DPACP) with solvatochromism, aggregation-induced emission (AIE) and mechanofluorochromic (MFC) enhancement characteristics was rationally designed and synthesized by attaching bulky diphenylamine electron-donor and pivalate ester electron-acceptor to coumarin. With solvent polarity increase from n-hexane to acetonitrile, this molecular displayed a bathochromic shift in the emission wavelength (from 436 nm to 553 nm) and a decrease in the quantum yield (from 81.1% to 2.8%), indicating solvatochromic effect. Also, the AIE behaviors were observed in CH3CN/water and THF/water mixture systems. For example, the PL intensity increased 6 times in mixed solvent (CH3CN: water = 10 : 90) compared to that in pure CH3CN. Moreover, the emission of original powder samples was red-shifted (from 438 nm to 483 nm) with fluorescence enhancement (the solid-state quantum yield increase from 19% to 28%) upon grinding, and the emission behaviors of grinding powder samples could be reverted to original state by wetting with n-hexane. Furthermore, the relationship among the molecular structure, intermolecular interactions and emission properties was investigated by single-crystal diffraction analysis. DPACP had a twisted conformation because of steric hindrance from diphenylamine and pivalate ester groups, which played a decisive role in realizing AIE and MFC enhancement behaviors. The absence of π-π stacking observed in single-crystal structure was the main reason for the AIE property. The MFC enhancement property could be ascribed to the disturbance of weak electrostatic interaction of adjacent molecules upon grinding. The bulky group of pivalate ester was first used to construct MFC molecule, and this work provided insights for developing AIE and MFC materials based on conventional planar fluorophore which was always subject to ACQ effect.

Aggregation-induced emission type fluorescent materials, preparation method and application

The invention discloses aggregation-induced emission type fluorescent materials, a preparation method and an application. The general structural formula of the fluorescent materials is shown in the description, wherein R represents a hydrogen atom, cyano

Facile construction of boranil complexes with aggregation-induced emission characteristics and their specific lipid droplet imaging applications

A rational strategy was reported to construct boranil complexes (DPFB derivatives) with unique aggregation-induced emission effects by installing phenyl rings in the anil ligand as the intramolecular rotors. In view of the good biocompatibility and suitab

Yellow-red emitting, methoxy substituted triphenylamine-based styryl derivatives: Synthesis, photophysical properties, viscosity sensitivity, aggregation induced emission, NLO properties, and DFT study

Three novel triphenylamine based fluorescent molecular rotors (FMRs) are designed and synthesized to study the effect of auxiliary methoxy substituent on aggregation induced emission (AIE) and viscosity sensitivity. Instead of elongated, short conjugated

Methoxy supported, deep red emitting mono, bis and tris triphenylamine-isophorone based styryl colorants: Synthesis, photophysical properties, ICT, TICT emission and viscosity sensitivity

A novel strategy for the synthesis of triphenylamine based and methoxy supported deep red emitting push-pull chromophores is developed. The methoxy groups though not in conjugation with the acceptor exhibited a red shifted absorption and emissions (670?nm

Red emitting triphenylamine based rhodamine analogous with enhanced Stokes shift and viscosity sensitive emission

Four novel structural hybrid analogues of Rhodamine B and Rhodamine 101 are synthesized by condensing N-substituted amino phenols with keto-acids of N-substituted phenols in presence of trifluoroacetic acid and are characterized by spectroscopic methods. Triphenylamine based derivatives show large Stokes shift (47 nm–69 nm) and red shifted emission (close to Near Infrared region) as compared to parent Rhodamine B and Rhodamine 101. These N-phenyl substituted dyes exhibited negative solvatochromism and pronounced viscosity sensitivity (14–24 folds increase in emission intensity) as compared to parent rhodamines. Polarity graphs and mathematically calculated charge transfer descriptors are in good correlations with observed trends. Computed values obtained by Density Functional Theory are in good agreement with the experimental results.

Deep red emitting triphenylamine based coumarin-rhodamine hybrids with large Stokes shift and viscosity sensing: Synthesis, photophysical properties and DFT studies of their spirocyclic and open forms

We designed and synthesized triphenylamine based and coumarin fused rhodamine hybrid dyes and characterized using 1H, 13C NMR and HR-LCMS analysis. Both the newly synthesized hybrid dyes were found to show red shifted absorption as well as emissions and large Stokes shift (40–68 nm) as compared to the small Stokes shift (25–30 nm) of reported dyes Rhodamine B and 101. Photophysical properties of these dyes were studied in different solvents and according to the solvents acidity or basicity they preferred to remain in their spirocyclic or open form in different ratio. We studied the spirocyclic as well as open form derivatives of these dyes for their viscosity sensitivity in three different mixture of solvents i.e. polar-protic [EtOH-PEG 400], polar-aprotic [toluene-PEG 400] and non-polar-aprotic [toluene-paraffin]. They are found to show very high viscosity sensitivity in polar-protic mixture of solvents [EtOH-PEG 400] and hence concluded that both polarity as well as viscosity factor worked together for the higher emission enhancement rather than only viscosity factor. As these dyes showed very high viscosity sensitivity in their spirocyclic as well as open form, they can be utilized as viscosity sensors in visible as well as deep red region. We also correlated our experimental finding theoretically by using Density Functional theory computations.

Monocarboxylate transporter 1 inhibitors as potential anticancer agents

Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.