6310-10-7Relevant academic research and scientific papers
Rational Design of Azo-Azomethine Receptors for Sensing of Inorganic Fluoride: Construction of Molecular Logic Gates and DFT Study
Khanmohammadi, Hamid,Rezaeian, Khatereh,Shabani, Nafiseh
, p. 1254 - 1262 (2017)
New azo-azomethine receptors, HLn (n≤1-3), have been synthesised via condensation reaction of 5-(4-X-phenyl)-azo-salicylaldehyde (X≤NO2, Cl and CH3) with (4-nitrobenzylidene)hydrazine. The receptor with a p-NO2 substituent on the aromatic ring of the azo moiety (HL1) has excellent sensitivity and selectivity towards basic anions with proper discrimination between F- and AcO- or H2PO4- in DMSO-water (4:1). A Job's plot displays a 1:1 stoichiometry between HL1 and F- alone with a detection limit of 0.737M for fluoride ions. The solvatochromic behaviour of HL1 was probed by studying its UV-vis spectra in four pure organic solvents of different polarities and a meaningful correlation was observed. Furthermore, HL1 was used for detection of inorganic fluoride in toothpaste. The systematic density functional theory (DFT) and time dependent-DFT calculations have been carried out to investigate the mechanism of colourimetric sensing of fluoride ion by HL1 in the gas phase and in solution. Moreover, by using F- and H+ as chemical inputs, and the absorbance as output, a INHIBIT logic gate was constructed, which exhibits 'Write-Read-Erase-Read' ability without obvious degradation in its optical output.
Ferrocene Appended Asymmetric Sensitizers with Azine Spacers with phenolic/nitro anchors for Dye-Sensitized Solar Cells
Chauhan, Ratna,Gosavi, Suresh W.,Kociok-K?hn, Gabriele,Kumar, Abhinav,Muddassir, Mohd.,Singh, Amita
, (2021/10/20)
Two extensively conjugated asymmetric ferrocene appended compounds with azine spacers, and phenolic and nitro groups as terminal groups with the following formulas Fc-CH=N-N=CH-p-C6H4-OH (Fc-OH) and Fc-CH=N-N=CH-p-C6H4-NO2 (Fc-NO2) (Fc= ferrocene) have been synthesized and characterized using micro-analyses, FTIR, 1H and 13C NMR, UV-Vis and for Fc-NO2 single crystal X-ray diffraction. The structural studies reveal that Fc-NO2 possess an extensively conjugated system where C5H4(Cp)-CH=N-N=CH-p-C6H4-NO2 is nearly planar which suggest strong electron communication from the ferrocene moiety to the p-C6H4-NO2 group via a -CH=N-N=CH- spacer. Both compounds have been used as sensitizers in titanium oxid based dye-sensitized solar cells (DSSCs) which indicate that amongst both sensitizers the Fc-OH one exhibited a better cell performance with Jsc 12.91 mA·cm?2, Voc 0.710 V, η 5.88% and incident photon to a current conversion efficiency of 53%. Electron injection in the conduction band of the titanium oxide semiconductor have been authenticated with the help of density of states calculations.
Synthesis, in-vitro and in-silico studies of triazinoindole bearing bis-Schiff base as β-glucuronidase inhibitors
Ahmad, Shakeel,Aziz, Aamir,Khan, Fahad,Rahim, Fazal,Sarfraz, Maliha,Taha, Muhammad,Ullah, Hayat,Wadood, Abdul
, (2021/07/16)
Triazinoindole bearing bis-Schiff base analogs (1–20) were synthesized by triazinoindole-thione ring formation, triazinoindole-thiol-phenylethanone, followed by triazinoindole bis-Schiff base formation. Synthesized analogs showed β-glucuronidase potential with IC50 value ranging between 2.60 ± 0.10 to 55.40 ± 1.60 μM as compared to standard D-saccharic acid 1,4-lactone (IC50 = 48.10 ± 1.2 μM). Analog 20 was the most potent one with IC50 value 2.60 ± 0.10 μM. Analogs 17, 4 showed IC50 values 5.20 ± 0.20 and 5.70 ± 0.20 μM respectively and withstand 2nd and 3rd ranked scaffolds among the synthesized analogs. All other sixteen analogs showed many-fold better potency with IC50 values ranging from 7.9 ± 0.2 to 48.1 ± 1.2 μM. The structure-activity relationship was established and confirmed of binding interactions through molecular docking studies.
Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes
Zhao, Zhensheng,Ma, Kevin C. Y.,Legault, Claude Y.,Murphy, Graham K.
supporting information, p. 11240 - 11245 (2019/08/20)
Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.
Metal-Free Construction of the C(sp3)-CF3 Bond: Trifluoromethylation of Hydrazones with Togni's Reagent under Mild Conditions
Zeng, Huiying,Luo, Zhen,Han, Xinlong,Li, Chao-Jun
supporting information, p. 5948 - 5951 (2019/08/29)
A metal-free trifluoromethylation of hydrazones with Togni's reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)-CF3 bonds.
Colorimetric anion sensors based on positional effect of nitro group for recognition of biologically relevant anions in organic and aqueous medium, insight real-life application and DFT studies
Singh, Archana,Sahoo, Suban K.,Trivedi, Darshak R.
, p. 596 - 610 (2017/08/07)
A new six colorimetric receptors A1-A6 were designed and synthesized, characterized by typical common spectroscopic techniques like FT-IR, UV–Visible, 1H NMR, 13C NMR and ESI-MS. The receptor A1 and A2 exhibit a significant naked-eye response towards F? and AcO? ions in DMSO. Due to presences of the NO2 group at para and ortho position with extended π-conjugation of naphthyl group carrying –OH as a binding site. Compared to receptor A2, A1 is extremely capable of detecting F? and AcO? ions present in the form of sodium salts in an aqueous medium. This is owed to the occurrence of –NO2 group at para position induced in increasing the acidity of –OH proton. Consequently, it easily gets deprotonated in aqueous media. The detection limit of receptor A1 was turned out to be 0.40 and 0.35?ppm for F? and AcO? ions which is beneath WHO permission level (1.0?ppm). Receptor A1 shows a solitary property of solvatochromism in different aprotic solvents in presence of AcO? ion. Receptor A1 depicts high selectivity towards AcO? ion in DMSO: HEPES buffer (9:1, v/v). Receptor A1 proved itself for real life application by detecting anion in solution and solid state. The binding mechanism of receptor A1 with AcO? and F? ions was monitored from 1HNMR titration and DFT study.
Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water
Aldoshin, Alexander S.,Tabolin, Andrey A.,Ioffe, Sema L.,Nenajdenko, Valentine G.
, p. 3816 - 3825 (2018/07/31)
The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.
Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation
Zhu, Dianhu,Lv, Leiyang,Li, Chen-Chen,Ung, Sosthene,Gao, Jian,Li, Chao-Jun
supporting information, p. 16520 - 16524 (2018/11/23)
Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
A Transition-Metal-Free and Base-Mediated Carbene Insertion into Sulfur-Sulfur and Selenium-Selenium Bonds: An Easy Access to Thio- and Selenoacetals
Arunprasath, Dhanarajan,Sekar, Govindasamy
, p. 698 - 708 (2017/02/23)
A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol-free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated. (Figure presented.).
Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones
Zhao, Zhensheng,Kulkarni, Kaivalya G.,Murphy, Graham K.
supporting information, p. 2222 - 2228 (2017/07/07)
We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non-α-stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).
