41097-51-2Relevant academic research and scientific papers
An Ullmann coupling of aryl iodides and amines using an air-stable diazaphospholane ligand
Yang, Minghua,Liu, Fei
, p. 8969 - 8971 (2007)
(Chemical Equation Presented) A copper-based catalytic system, using an air-stable diazaphospholane as the ligand, was developed for an efficient Ullmann reaction between aryl iodides and alkyl or heterocyclic amines.
Subtle structural variation in azine/imine derivatives controls Zn2+ sensitivity: ESIPT-CHEF combination for nano-molar detection of Zn2+ with DFT support
Khanra, Somnath,Ta, Sabyasachi,Ghosh, Milan,Chatterjee, Sudeshna,Das, Debasis
, p. 21302 - 21310 (2019)
Excited-state intra-molecular proton transfer (ESIPT)-active imine and azine derivatives, structurally characterised by XRD, and denoted L1, L2, L3 and L4, possess weak fluorescence. The interaction of these probes with Zn2+ turns ON the fluorescence to allow its nano-molar detection. Among the four ESIPT-active molecules, L2, L3 and L4 are bis-imine derivatives while L1 is a mono-imine derivative. Among the three bis-imine derivatives, one is symmetric (L3) while L2 and L4 are unsymmetrical. The lowest detection limits (DL) of L1, L2, L3 and L4 for Zn2+ are 32.66 nM, 36.16 nM, 15.20 nM and 33.50 nM respectively. All the probes bind Zn2+ (105 M-1 order) strongly. Computational studies explore the orbital level interactions responsible for the associated photo-physical processes.
Selective electrochemical determination of trace level copper using a salicylaldehyde azine/MWCNTs/Nafion modified pyrolytic graphite electrode by the anodic stripping voltammetric method
Liao, Yuan,Li, Qian,Yue, Ying,Shao, Shijun
, p. 3232 - 3238 (2015)
A novel Cu2+ electrochemical sensor based on a salicylaldehyde azine/MWCNTs/Nafion-modified pyrolytic graphite electrode was prepared for anodic stripping analysis of Cu2+. Salicylaldehyde azine was synthesized and then used for the selective determination of the heavy metal pollutant Cu2+ due to its azine structure, which gave selective complexing ability toward Cu2+. The use of MWCNTs with their strong adsorption ability could greatly enhance the sensitivity. Nafion, a proton-exchange polymer, was used as the conductive matrix in which the salicylaldehyde azine and MWCNTs could be strongly fixed to the substrate electrode surface. The as-prepared electrochemical sensor showed remarkably enhanced selectivity and sensitivity towards Cu2+. The response current of the sensor was linear with Cu2+ concentration ranging from 5 to 300 nM under 15 min accumulation at open-circuit potential, with a very low detection limitation of about 1 nM. The hybrid functionalized electrode also exhibited good selectivity to avoid the interference of other heavy metal ions like Cd2+, Pb2+ and Hg2+ in the mixture solution together with Cu2+. Real application towards environmental sample analysis confirmed that the modified electrode could be applied for the selective determination of trace levels of Cu2+ in the Yellow River.
Excited state intramolecular single proton transfer mechanism of pigment yellow 101 in solid state: Experiment and DFT calculation
Shen, Shen,Liu, Xian,Sun, Jianqi,Wang, Mingda,Jiang, Zhengjun,Xia, Guomin,Wang, Hongming
, p. 93 - 100 (2019)
To investigate fluorescence mechanism of Pigment Yellow 101 (P. Y. 101) in solid state, three aromatic aldehyde azines (1–3) including P. Y. 101 have been synthesized and compared with each other. Results indicated that P. Y. 101 prepared by solvothermal method is actually the mixture of two polymorphs, whose molecular packing mode can be transformed into each other by recrystallizing or external stimuli such as pressure and grinding. The ESIPT properties of 1–3 were investigated by DFT/TD-DFT calculations and time-correlated single photon counting (TCSPC) technique. Both experimental and theoretical results revealed that the dual fluorescence properties of P. Y. 101 in solid state are ascribed to the excited-state intramolecular single proton transfer fluorescence emissions of two structurally different polymorphs rather than the results of the sequential or concerted excited-state intramolecular double proton transfers, which provide a potential valuable tool for developing multistimuli-responsive luminescent materials.
Crystal structure and feasibility of intramolecular proton transfer reaction of salicylaldazine
Mijanuddin,Sheldrick,Mayer-Figge,Ali, Mahammad,Chattopadhyay, Nitin
, p. 161 - 165 (2004)
The work describes characterization of salicylaldazine by IR, NMR and single crystal X-ray diffraction studies. The compound crystallizes in the monoclinic crystal system with the space group P21/n, a=8.554(3), b=6.338(2), c=11.864(5)?, and β=107.89(2)°. There are two strong intramolecular hydrogen bonds of the type O-H?N and two weak hydrogen bridges of the type C-H?O which help the molecules to pack in a layered structure. Semi-empirical calculations have been performed to predict theoretically the feasibility of intramolecular ground and/or excited state proton transfer reaction/s. Potential energy curves have been generated in the ground (S0) and the lowest excited (S1) singlet states to judge the feasibility of intramolecular single and double proton transfer reactions. Semi-empirical (AM1) calculations suggest that only the excited state intramolecular single proton transfer process is favored both thermodynamically and kinetically. No other prototropic processes are theoretically feasible.
Design, synthesis and biological evaluation of Schiff’s base derivatives as multifunctional agents for the treatment of Alzheimer’s disease
Shi, Jian,Zhou, Yi,Wang, Keren,Ma, Qinge,Wei, Rongrui,Li, Qingfeng,Zhao, Yiyang,Qiao, Zhanpin,Liu, Shuang,Leng, Yumin,Liu, Wenmin,Sang, Zhipei
, p. 624 - 634 (2020/11/30)
A series of Schiff’s base derivatives was rationally designed, synthesized, and evaluated as multi-function agents for the treatment of Alzheimer’s disease (AD). The results revealed that compound 3b was a novel multifunctional agent. It acted as a highly selective monoamine oxidase-B inhibitor (IC50 = 8.4 nM), which was explained by the docking study. Compound 3b also was an antioxidant agent (2.3 eq) and could significantly inhibit self-induced Aβ1-42 aggregation (31.8%). Meanwhile, compound 3b was a selective metal chelator and could inhibit Cu2+-induced Aβ1-42 aggregation (62.3%). Furthermore, compound 3b presented good neuroprotective effects on H2O2-induced PC12 cell injury. More importantly, compound demonstrated good blood brain barrier permeability and druglike properties. Therefore, compound 3b, a promising multi-targeted active molecule, offers an attractive starting point for further study in the drug-discovery process against AD.[Figure not available: see fulltext.].
A New Alternative Synthesis of Salicylaldazine via Microwave Irradiation Method
Kassim, Karimah,Hamali, Muhamad Azwan,Yamin, Bohari
, (2019/06/06)
Two diazine Schiff base ligands, HLa and HLb, derived from thiocarbohydrazide and salicylaldehyde derivatives were synthesized using the microwave-assisted synthesis approach. The confirmation of both ligands was elucidated through physiochemical and spectroscopy techniques as well as single X-ray crystallography diffraction. The analyses showed that the ligands synthesized were formed as azine instead of thiocarbohydrazone based on the missing thione, C=S moiety, throughout FTIR and NMR spectrascopic data. This finding was further concluded by X-ray crystal analysis. The biological properties of these ligands were screened using the disc diffusion method. The result shows that HLb shows significant inhibition towards all of the bacteria tested.
Tunable Color of Aggregation-Induced Emission Enhancement in a Family of Hydrogen-Bonded Azines and Schiff Bases
Guieu, Samuel,Cardona, Francisco,Rocha, Jo?o,Silva, Artur M. S.
supporting information, p. 17262 - 17267 (2018/11/10)
A simple synthesis strategy afforded a family of hydrogen-bonded azines and Schiff-bases. Although in dilute solution these dyes are faint light emitters, all exhibit bright luminescence upon aggregation. Changing the peripheral substituents from electron donating to electron withdrawing allows emission fine-tuning in a range from bluish-green to orange-red. The crystal structures of the materials reveal that the restriction of intramolecular rotations is the main mechanism for the aggregation-induced emission enhancement properties.
Fluorine ion detection probe based on aggregation-induced emission as well as preparation method and application of fluorine ion detection probe
-
Paragraph 0048-0050, (2017/07/07)
The invention discloses a fluorine ion detection probe based on aggregation-induced emission as well as a preparation method and application of the fluorine ion detection probe. The structure of a fluorescent probe is shown as a formula (I); the fluorescent probe is formed by taking salicylic aldehyde as a raw material, forming salicylic aldehyde azine through the raw material and hydrazine hydrate and carrying out silicon protection. The probe disclosed by the invention has stable optical performances, high fluorine ion detection sensitivity and low detection lower limit; the detection limit is 1mu.M and a response range is 1mu.M to 50mu.M. The fluorine ion detection probe has good selectivity and no response on negative and positive ions including chlorine ions, bromine ions, iodate ions, periodate ions, nitrate ions, nitrite ions, acetate ions, carbonate ions, sulfate ions, sulfite ions, silver ions, barium ions, calcium ions, lithium ions, magnesium ions, ammonium ions, nickel ions, zinc ions and the like. The fluorine ion detection probe has the advantages of simple synthesis, moderate conditions and high yield. The fluorescent molecular probe has an actual application value in the fields of biochemistry and environmental chemistry, especially detection of fluorine ions in water and the like. (The formula (I) is shown as the description.).
A family of silatrane-armed triazole-encapped salicylaldehyde-derived Schiff bases: Synthesis, spectral analysis, and antimicrobial and quantum chemical evaluation
Singh, Gurjaspreet,Arora, Aanchal,Rani, Sunita,Kalra, Pooja,Aulakh, Darpandeep,Wriedt, Mario
, (2017/09/26)
This work describes the successful synthesis of salicylaldehyde-derived Schiff base-linked organosilicon compounds following a highly efficient click approach. Hydroxyl-terminated Schiff bases were alkylated to bis-acetylenes (1–3) which upon 3?+?2 cycloaddition with 3-azidopropyltriethoxysilane yielded triazole-decorated bis-silanes (4–6). These silanes further underwent base-catalyzed transesterification to afford Schiff base-linked triazole-bound organosilatranes (7–9). The final silatranes as well as precursor alkynes and silanes were comprehensively characterized using NMR (1H and 13C) and infrared spectroscopic techniques together with elemental analysis and mass spectrometry of compounds 7–9. Also, the structures of alkynes 1–3 and silatrane 7 were validated using single-crystal X-ray crystallography. Organosilatranes were initially screened for their pharmacokinetic profile using absorption, distribution, metabolism, excretion and toxicity (ADMET) tools and then explored for their antimicrobial activities, with compound 9 emerging as the most potent antimicrobial agent. Compounds 1–3 and 7–9 also underwent thorough computational analysis by applying the density functional theory (DFT) approach with B3LYP/6-31G(d) level of theory and the results were found to be consistent with the experimental data. Several DFT-based descriptors were also evaluated providing a valuable insight into molecular stability and reactivity.
