42910-72-5Relevant academic research and scientific papers
Designing multistep transformations using the Hammett equation: Imine exchange on a Copper(I) template
Schultz, David,Nitschke, Jonathan R.
, p. 9887 - 9892 (2006)
Herein, we quantify how imine exchange may be used to selectively transform one metalloorganic structure into another. A series of imine exchange reactions were studied, involving a set of 4-substituted anilines, their 2-pyridylimines and 1,10-phenanthrolyl-2,9-diimines, as well as the copper complexes of these imine ligands. Electron-rich anilines were found to displace electron-poor anilines in all cases. Linear free energy relationships (LFERs) were discovered connecting the electron-donating or -withdrawing character of the 4-substituent of an aniline, as measured by the Hammett σpara parameter, to that aniline's ability to compete with unsubstituted aniline to form imines. The quality of these LFERs allowed for quantitative predictions: to obtain the desired degree of selectivity in an imine exchange between anilines A and B, the required σpara differential could be predicted using a variant of the Hammett equation, log(KAB) = ρ(σA - σB). We validated this methodology by designing and executing a three-step transformation of a series of copper(I)-containing structures. Each step proceeded in predictably high yield, as calculated from σ differentials. At each step in the series of transformations, macrocyclic structures could be created or destroyed through the selection of mono- or di-amines as subcomponents. The same methodology could be used to predict the formation of a diverse dynamic library of helicates from a set of four aniline precursors, as well as the collapse of this library into one helicate upon the addition of a fifth aniline.
Different conjugated system Zn(II) Schiff base complexes: Supramolecular structure, luminescent properties, and applications in the PMMA-doped hybrid materials
Dong, Yu-Wei,Fan, Rui-Qing,Chen, Wei,Zhang, Hui-Jie,Song, Yang,Du, Xi,Wang, Ping,Wei, Li-Guo,Yang, Yu-Lin
, p. 1266 - 1276 (2017)
A series of Zn(ii) complexes with different conjugated systems, [ZnL1Cl2]2 (Zn1), [ZnL2Cl2] (Zn2), [Zn(L3)2]·(ClO4)2 (Zn3), [Zn2L4Cl4] (Zn4), and [ZnL5Cl2] (Zn5), were synthesized and subsequently characterized via single crystal X-ray diffraction, 1H and 13C NMR, FT-IR, elemental analyses, melting point, and PXRD. The X-ray diffraction analyses revealed that the supramolecular frameworks of complexes Zn1-Zn5 are constructed by C-H?O/Cl hydrogen bonds and π?π interactions. Complexes Zn1-Zn3 feature 3D 6-connected {412·63} topological structures, whereas complex Zn4 exhibits a 3D 7-connected supramolecular framework with a {417·64} topological structure. However, complex Zn5 shows one-dimensional "wave-like" chains. Based on these varied structures, the emission maximum wavelengths of complexes Zn1-Zn5 can be tuned in a wide range of 461-592 nm due to the red shift direction of λem caused by different conjugated systems and their electron donating abilities. Complex Zn3 shows a strong luminescence in the solid state and in the acetonitrile solution. Therefore, a series of Zn3-poly(methylmethacrylate) (Zn3-PMMA) hybrid materials were obtained by controlling the concentration of complex Zn3 in poly(methylmethacrylate) (PMMA). At an optimal concentration of 4%, the doped polymer film of Zn3-PMMA displays strong green luminescence emissions that are 19-fold in the luminescence intensities and 98 °C higher in the thermal stability temperature compared to the Zn3 film.
Aryl variation and anion effect on CT-DNA binding and in vitro biological studies of pyridinyl Ag(I) complexes
Adeleke, Adesola Abimbola,Islam, Md. Shahidul,Sanni, Olakunle,Mocktar, Chunderika,Zamisa, Sizwe J.,Omondi, Bernard
, (2020/11/09)
Synthesis and spectroscopic characterization of five ligands ((E)-2-((pyridin-2-ylmethylene)amino)phenol L1, 2-(pyridin-2-yl)benzo[d]thiazole L2, (E)-N-(2-fluorophenyl)-1-(pyridin-2-yl)methanimine L3, (E)-1-(pyridin-2-yl)-N-(p-tolyl)methanimine L4 and (E)
(E)-N-(Pyridine-2-ylmethylene)arylamine as an Assembling Ligand for Zn(II)/Cd(II) Complexes: Aryl Substitution and Anion Effects on the Dimensionality and Luminescence Properties of the Supramolecular Metal-Organic Frameworks
Dong, Yu-Wei,Fan, Rui-Qing,Wang, Xin-Ming,Wang, Ping,Zhang, Hui-Jie,Wei, Li-Guo,Chen, Wei,Yang, Yu-Lin
, p. 3366 - 3378 (2016/06/14)
Using five Schiff base ligands (E)-N-(pyridine-2-yl) (CH=NPhR) (where R = 4-CH3, L1; 2,6-(CH3)2, L2; 2,4,6-(CH3)3, L3; 2,6-(C2H5)2, L4; 2,6-(i-C3H7)2, L5), nine Zn(II)/Cd(II) complexes, namely, Zn1-Zn3, Cd1, Cd2, Cd3a, Cd3b, Cd4, and Cd5, have been successfully synthesized. The structures of the Zn(II)/Cd(II) complexes have been established by single crystal X-ray diffraction and further physically characterized by 1H NMR, FT-IR, and elemental analysis. The crystal structures of these complexes indicate that the structures of ligand and anions can directly influence the formation of 1D → 3D supramolecular metal-organic frameworks (SMOFs) via C-H···O/C-H···Cl hydrogen bonds and π···π interactions. Upon irradiation with UV light, the nine Zn(II)/Cd(II) complexes display deep blue emissions of 401-436 nm in acetonitrile solution and light blue or bluish green emissions of 485-575 nm in the solid state, respectively. The photoluminescence properties of nine Zn(II)/Cd(II) complexes can be finely and predictably tuned over a wide range of wavelengths by small and easily implemented changes to ligand structure. It is worth noting that Zn1 and Cd1 exhibit obvious aggregation-induced emission enhancement (AIEE) properties in the CH3CN-H2O mixture solutions.
Topological Evolution in Mercury(II) Schiff Base Complexes Tuned through Alkyl Substitution – Synthesis, Solid-State Structures, and Aggregation-Induced Emission Properties
Dong, Yu-Wei,Fan, Rui-Qing,Wang, Xin-Ming,Wang, Ping,Zhang, Hui-Jie,Wei, Li-Guo,Song, Yang,Du, Xi,Chen, Wei,Yang, Yu-Lin
, p. 3598 - 3610 (2016/08/09)
From two series of Schiff base ligands, (E)-N-(pyridine-2-yl)(CMe=NPhR) and (E)-N-(pyridine-2-yl)(CH=NPhR) [R = H, L1a, L1b; 2-CH3, L2a, L2b; 4-CH3, L3a, L3b; 2,6-(CH3)2, L4a, L4b; 2,6-(C2H5/sub
Insight into inhibition of the human amyloid beta protein precursor (APP: PDB ID 3UMI) using (E)-N-(pyridin-2-ylmethylene)arylamine (LR) models: Structure elucidation of a family of ZnX2-LR complexes
Basu Baul, Tushar S.,Kundu, Sajal,Singh, Palwinder,Shaveta,Guedes Da Silva, M. Ftima C.
, p. 2359 - 2369 (2015/01/30)
The amyloid beta precursor protein (APP) and its neurotoxic cleavage product amyloid beta (Aβ) are a cause of Alzheimer's disease and appear essential for neuronal development and cell homeostasis. Proteolytic processing of APP is influenced by metal ions
Synthesis, characterization, photoluminescent properties and supramolecular aggregations in diimine chelated cadmium dihalides
Basu Baul, Tushar S.,Kundu, Sajal,Ng, Seik Weng,Guchhait, Nikhil,Tiekink, Edward R.T.
, p. 96 - 119 (2014/03/21)
A series of 12 new cadmium compounds, [Cd(X2)(L)] (4, 10), [Cd(X2)(L)(DMSO)] (9), [Cd(X2)(L)]2 (1-3, 5, 7, 8, 11, and 12), and [Cd(Cl2)2(L)]n (6) where X = chloride, bromide, and
Aerobic oxidative coupling of alcohols and amines over Au-Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines
Zhang, Leilei,Wang, Wentao,Wang, Aiqin,Cui, Yitao,Yang, Xiaofeng,Huang, Yanqiang,Liu, Xiaoyan,Liu, Wengang,Son, Jin-Young,Oji, Hiroshi,Zhang, Tao
supporting information, p. 2680 - 2684 (2013/10/08)
A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au-Pd alloy catalysts (Au-Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.
Antifungal and cytotoxic activities of some N-substituted aniline derivatives bearing a hetaryl fragment
Kouznetsov, Vladímir V.,Vargas Méndez, Leonor Y.,Sortino, Maximiliano,Vásquez, Yelkaira,Gupta, Mahabir P.,Freile, Mónica,Enriz, Ricardo D.,Zacchino, Susana A.
, p. 794 - 809 (2008/09/17)
Diverse N-substituted anilines bearing hetaryl fragments were easily prepared from corresponding aldimines derived from commercially available aromatic aldehydes and anilines. 2-Furyl substituted anilines showed very good antifungal activities against dermatophytes, particularly against Trichophyton rubrum (MIC = 3.12-6.25 μg/mL). In addition, all active compounds, 45-47, 73, and 74, were tested for cytotoxic activities against breast (MCF-7), lung (H-460), and central nervous system (SF-268) human cancer cell lines with the NCI-anticancer-drug screen. The activity of amines described in this paper, along with the low toxicity of most of them, shows promise for the future development of non-toxic new antimycotic agents.
In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers
Vargas M., Leonor Y.,Castelli, Maria V.,Kouznetsov, Vladimir V.,Urbina G., Juan M.,Lopez, Silvia N.,Sortino, Maximiliano,Enriz, Ricardo D.,Ribas, Juan C.,Zacchino, Susana
, p. 1531 - 1550 (2007/10/03)
The synthesis, in vitro antifungal evaluation and SAR studies of 101 compounds of the 4-aryl-, 4-alkyl-, 4-pyridyl or -quinolinyl-4-N-arylamino-1-butenes series and related compounds, are reported here. Active structures showed to inhibit (1,3)-β-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.
