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DYES AND PIGMENTS · 2020 · IF 4.613

Ratiometric fluorescent strategy for malononitrile determination in organic and aqueous medium and biological imaging

Yan Gong,Xinjie Guo,Baohui Teng,Qian Zhang,Peng Zhang,Caifeng Ding

Malononitrile is a versatile dinitrile compound with high reactivity, which has wide prospect in application for multisynthetic organic medical chemistry and industrial manufacture. Considering of the transformation to HCN in animal tissue metabolism, malononitrile has potential environmental pollution and health risks. Here, a ratiometric fluorescent probe 4-(benzothiazol-2-yl)-2-hydroxy benzaldehyde (HBTA) for detection of malononitrile in organic and aqueous phase is developed on the basis of reaction-triggered fluorophore for the first time. The ratiometric assay with malononitrile-responsive fluorescence signal was contributed by Knoevenagel condensation and intramolecular cyclization , which was confirmed by HR-MS analysis and NMR titration spectra. In addition, this ratiometric probe provided a fancy strategy for detection of malononitrile with fast response, high sensitivity and selectivity, declaring excellent imaging performance in vivo capable of semi-quantification for malononitrile level.

研究领域: 有机化学 · 分析化学 · 环境科学 · 生物医学
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NEW JOURNAL OF CHEMISTRY · 2021 ·Vol. 45 ·期 18 ·8155-8165 · IF 3.591

One-step construction of a novel AIE probe based on diaminomaleonitrile and its application in double-detection of hypochlorites and formaldehyde gas

Xiaoye Wen,Li Yan,Zhefeng Fan

As the environmental residues of formaldehyde and hypochlorites are very harmful to human health, a new simple and efficient aggregation-induced emission probe based on diaminomaleonitrile was designed and applied in the independent detection of hypochlorites and formaldehyde. The probe shows high selectivity and anti-interference ability against other potential competitive substances. ClO− promotes the oxidized splitting of CN in the probe, and induces evident color changes visible to the naked eye together with quenched fluorescence. The detection of ClO− by this probe was fast, sensitive, and visible to the naked eye. The detection limit of the probe to ClO− in the range of 0.70–20 μM is 18 nM. Through the condensation mechanism and with amine as the binding site of formaldehyde, the exposed amino group in the probe structure responds sensitively and efficiently to formaldehyde. The probe can effectively monitor 0.50–25 μM formaldehyde in aqueous solutions, with a detection limit as low as 42 nM. A portable solid sensor – a formaldehyde detection plate was built by directly covering the probe on a thin-layer chromatography plate. Thereby, formaldehyde gas can be effectively and sensitively detected, which offers a clue for developing solid-state formaldehyde-detection plates. The high experimental recovery rates prove that this new probe is highly promising in hypochlorite detection in the real water environment.

研究领域: 分析化学 · 环境科学 · 生物医学
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Catalysts · 2019 ·Vol. 10 ·期 1 ·14 · IF 3.444

Asymmetric Michael Addition of Malononitrile with Chalcones via Rosin-Derived Bifunctional Squaramide

Ning Lin,Qiu-Xiang Wei,Li-Hua Jiang,Yan-Qiu Deng,Zhen-Wei Zhang,Qing Chen

A rosin-derived bifunctional squaramide catalyzed asymmetric Michael addition of malononitrile with chalcones was discovered. This protocol provides a methodology for the facile synthesis of chiral γ-cyano carbonyl compounds in high yields and enantioselectivities (up to 99% yield and 90%ee) with a lower catalyst loading (0.3 mol%). The predominantR-configured adducts were obtained by this organocatalystic reaction, according to the experimental findings.Keywords:asymmetric catalysis;michael addition;malononitrile;chalcone;rosin-derived bifunctional catalyst

研究领域: 有机化学 · 催化化学
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CHEMICAL ENGINEERING JOURNAL · 2019 · IF 8.355

Diaminomaleonitrile functionalized double-shelled hollow MIL-101 (Cr) for selective removal of uranium from simulated seawater

Jichi Zhang,Hongsen Zhang,Qi Liu,Dalei Song,Rumin Li,Peili Liu,Jun Wang

Hollow metal-organic frameworks (MOFs) have attracted wide interest because of their unique core-shell structure. As a novel uranium adsorbent, diaminomaleonitrile (DAMN) functionalized double-shelled hollow (DSHM) metal-organic framework of chromium(III) terephthalate was prepared by a post-synthetic method of grafting amino group onto coordinatively unsaturated sites (CUS). TEM, XRD, nitrogen sorption and FT-IR spectrometry were used to characterize the obtained DAMN functionalized hollow MOF. The maximum capacity of uranium adsorption is 601 mg g −1 , which exceeds all known functionalized MIL-101 uranium adsorption materials. The optimal adsorption pH is 8 which is close to the pH of seawater. Furthermore, the high selectivity of uranium and high adsorption rate in simulated seawater provide a promising prospect to introduce DSHM-DAMN for the extraction of uranium from seawater. In this work, we first applied hollow MOF for uranium adsorption, which greatly improves the uranium adsorption performance of MOF materials; we also explored the practical application of hollow MOF materials.

CAS / MDL: 7789-02-8 100-21-0
研究领域: 材料科学 · 环境科学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Novel diaminomaleonitrile-based fluorescent probe for ratiometric detection and bioimaging of hypochlorite

Yuliang Jiang,Shishan Wu,Can Jin,Bingxiang Wang,Jian Shen

Highly sensitive and selective detection for hypochlorite anion (OCl − ) is of extreme significance due to its important role and function in biological systems. Herein, a diaminomaleonitrile derivative (DMD) has been developed as a novel ratiometric and colorimetric fluorescent probe for OCl − detection. Consistent with the UV–vis spectral change, the probe DMD exhibited promptly a color change from canary yellow to gules upon the addition of OCl − , which could be easily observed by naked-eyes. In addition, the detection limit was found to be 0.5 nM, which is much lower than that of many reported OCl − probes. More importantly, owing to its excellent sensing properties and negligible cytotoxicity, probe DMD can be conveniently applied to image intracellular OCl − in living cells, indicating it a promising tool in biological applications.

研究领域: 分析化学 · 生物化学 · 医学
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JOURNAL OF ORGANIC CHEMISTRY · 2018 · IF 4.805

One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3-d]pyrimidines and Furo[2,3-d]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide

Zhen-Hua Li,Zhi-Jiang Jiang,Qiao-Ling Shao,Jin-Jing Qin,Qiang-Feng Shu,Wen-Hao Lu,Wei-Ke Su

A one-pot cascade heterocyclization strategy has been developed for the synthesis of 2,4-dichloro-substituted pyrano[2,3-d]pyrimidines and furo[2,3-d]pyrimidines from linear γ- and β-ketomalononitriles using triphosgene and triphenylphosphine oxide. The reaction afforded synthetic useful products with moderate to good yields, bypassing the conventional harsh conditions of chlorination. The mechanistic study revealed that the reaction proceeded with a non-isocyanate route, and the second step may conduct in a triphenylphosphine oxide-catalyzed manner.

研究领域: 有机化学 · 药物化学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2018 · IF 2.891

Dye-sensitized hematite compososite photocatalyst and its photocatalytic performance of aerobic annulation

Dong-Liang Huang,Peng-Li Zhang,Ling-Ling Qu,Qiu-Yun Chen

A visible light initiated catalyst (DP-pfa@Fe 2 O 3 ) is synthesized and used as a photocatalyst for the synthesis of pyrazoles under mild reaction conditions. Holes (h + ) and   OH are the essential for the light-induced the pyrazole annulation reaction using water as oxygen source. Results demonstrate that photocatalyzed reaction of methyl hydrazine and 2-benzylidenemalononitrile produced 2-((2-methylhydrazinyl)(phenyl)methylene)malononitile, which can transfer into pyrazoles in the presence of ∙ OH. Our results provide a new catalyst and an economic synthetic method for the synthesis of pyrazoles through aerobic annulation.

研究领域: 化学 · 材料科学 · 催化 · 有机合成
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Journal of Environmental Chemical Engineering · 2024 · IF 7.4

Synergistic and efficient sorption of uranium by amidoxime-based chitosan with multiple functional groups

Lirong Yang,Fengying Chen,DePing Chen,Jianguo Gao,Hui Ju,Jie Tang,Qiaoling Jiang,Xiaojun Wang

A novel amidoxime-modified chitosan (CS-AO) containing amidoxime, amino and Schiff base was prepared, by introducing diaminomaleonitrile (DAMN) which contains both amino and nitrile groups into chitosan. CS-AO has a very good synergistic uranium sorption property with high efficiency, with the maximum uranium sorption capacity up to 596 mg/g, and 243.2 μg/g in seawater; besides, after four cycles of sorption-desorption, more than 90 % of its initial uranium sorption capacity is still left. In addition, the uranium sorption of the adsorbent is mainly carried out through the coordination of amidoxime with uranium, followed by amino and Schiff base. The sorption process is fitted by pseudo-second-order kinetics, Langmuir and Sips isothermal models. It is controlled primarily by chemisorption , as well as monolayer sorption and multilayer sorption, which is a spontaneous endothermic process.

研究领域: 材料科学 · 环境化学 · 核工程
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