53338-51-5

Upstream product

• 4181-05-9 4-(diphenylamino)benzaldehyde 
• 603-34-9 N,N-diphenylaminobenzene 

Relevant academic research and scientific papers

Excited state intramolecular proton transfer induced fluorescence in triphenylamine molecule: Role of structural conformation and reversible mechanofluorochromism

Triphenylamine (TPA) based Schiff base molecules (1–4) were synthesized and role of molecular structure and conformation on excited state intramolecular proton transfer (ESIPT) induced fluorescence in both solution as well as solid state has been explored

Azine based AIEgens with multi-stimuli response towards picric acid

Multifunctional aggregation induced emission luminogens (AIEgens) are novel materials which have significant applications in various fields including biomedical, optoelectronics and sensors. Enormous efforts have been directed towards the strategic development and characterisation of AIEgens, in order to better understand the AIE mechanism. Herein, we studied the photophysical properties of symmetrical azine (D-π-D) based AIEgens in detail by varying the solvent polarity and viscosity. The AIE behaviour of the azine derivatives relies on the substituents on the nitrogen atom of the amine moiety. Further, these azine derivatives sense the picric acid (PA) with high selectivity and sensitivity in both monomer and aggregated forms. The hydrogen bonding interaction of PA with any one side of the amine nitrogen leads to the formation of a new intramolecular charge transfer state which results in the formation of new absorption and emission spectra. Interestingly in the presence of PA, azine monomers exhibit fluorescence enhancement in pure THF, while aggregated azine molecules show fluorescence quenching in THF-water mixtures.

N,N-disubstituted azines attenuate LPS-mediated neuroinflammation in microglia and neuronal apoptosis via inhibiting MAPK signaling pathways

Background: Activated microglia interact with astrocytes and neuronal cells to induce neuroinflammation, which can contribute to the pathogenesis and progression of Alzheimer's and Parkinson's disease. To identify the most effective anti-neuroinflammatory agent, we designed and synthesized a family of 13 new azine derivatives and investigated their anti-neuroinflammatory activities in LPS-activated BV-2 microglial cells. Results: Out of 13 derivatives, compound 3 [4,4'-(1E,1'E,3E,3'E)-3,3'-(hydrazine-1,2-diylidene) bis-(prop-1-ene-1-yl-3-ylidene) bis-(2-methoxyphenol)] exhibited excellent anti-neuroinflammatory activities (IC50 = 12.47 μM), which protected neurons from microglia-mediated neurotoxicity. Specifically, the anti-neuroinflammatory effects of compound 3 inhibited MAPK signaling pathways through the inhibition of p38 and JNK mediated signaling and the production of pro-inflammatory cytokines, and inflammatory mediators. Additionally, compound 3 strongly exhibited neuroprotective effect by inhibiting LPS-mediated necrosis and apoptosis. Preliminary SAR analysis suggests that the presence of methoxyphenol and the substitution pattern within hydrazine may influence the anti-neuroinflammatory activity. FACS analysis also strongly supports the neuroprotective effect of compound 3. Conclusions: Based on our results, the compound 3 exhibited excellent anti-neuroinflammatory activity against LPS-activated microglia, which resulted in the inhibition of neuronal apoptosis and neuronal degeneration.

Photophysical properties of isoelectronic oligomers with vinylene, imine, azine and ethynylene spacers bearing triphenylamine and carbazole end-groups

Ten symmetrical oligomers containing either triphenylamine or carbazole substituents as end-groups and 1,4-phenylenevinylene, 1,4-phenylene imine, azine and 1,4-phenylene ethynylene as π-spacers, have been synthesized by polycondensation reactions between aromatic aldehydes (4- formyltriphenylamine and 3-formyl N-hexylcarbazole) or iodides (4-iodotriphenylamine and 3-iodo Nhexylcarbazole) with bisphosphonate derivative, 1,4-diaminobenzene, hydrazine or 1,4- diethynylbenzene, respectively. These oligomers are models for the corresponding conducting polymers, have a well-defined molecular structure, can be highly purified using common methods and processed as thin films by vacuum evaporation, dip or spin coating. The oligomers preserve all of the properties and potential applications of the corresponding polymers. The structural characterization of these oligomers was performed using usual spectroscopic methods (1H-RMN, FT-IR and DSC) and their photophysical properties were analyzed by UVeVis and fluorescence spectroscopy. Their redox properties were studied by cyclic voltammetry.

Comparative studies of structural, thermal, optical, and electrochemical properties of azines with different end groups with their azomethine analogues toward application in (opto)electronics

Two series of azines and their azomethine analogues were prepared via condensation reaction of benzaldehyde, 2-hydroxybenzaldehyde, 4-pyridinecarboxaldehyde, 2-thiophenecarboxaldehyde, and 4-(diphenylamino) benzaldehyde with hydrazine monohydrate and 1,4-phenylenediamine, respectively. The structures of given compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy as well as elemental analysis. Optical, electrochemical, and thermal properties of all compounds were investigated by means of differential scanning calorimetry (DSC), UV-vis spectroscopy, stationary and time-resolved photoluminescence spectroscopy, and cycling voltammetry (CV). Additionally, the electronic properties, that is, orbital energies and resulting energy gap were calculated theoretically by density functional theory (DFT). Influence of chemical structure of the compounds on their properties was analyzed.