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DYES AND PIGMENTS · 2019 · IF 4.018

Synthesis, characterization and photophysical properties of meso-indole-boron-dipyrromethene derivatives and their cell imaging and viscosity sensing

Ben Dong,Kailiang Zhong,Yun Lu

Based on the molecular design and structural modification of boron-dipyrromethene (BODIPY), two new BODIPY derivatives with meso -substituted functional indole moieties were successfully prepared. These new compounds were characterized by NMR, HRMS and FTIR , exhibiting the different UV–vis and PL spectral phenomena because of their varied molecular structures in various solvents and different degrees of negative solvatochromism. Theoretical calculations and CV results show that the substituted NO 2 group at 5-position of indole is favorable for increasing the oxidation potential of the molecules, while the NH 2 group is the opposite. These two BODIPY derivatives have different sensitivities to pH changes, and can be appropriately applied as cell imaging materials due to their good physical chemical characteristics and excellent biocompatibility. In particular, the fluorescence characteristics of BODIPY derivative with the substituted NH 2 group at 5-position of indole show a good solvent viscosity dependence, highlighting its potential application for testing the intracellular viscosity changes of the living cell in disease diagnosis.

CAS / MDL: 111-25-1 120-72-9
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BIOCHEMICAL ENGINEERING JOURNAL · 2019 · IF 3.371

Effect of nitrate on indole degradation characteristics and methanogenesis under mixed denitrification and methanogenesis culture

Yanjuan Gao,Guoying Wang,Aijuan Zhou,Xiuping Yue,Yanqing Duan,Xin Kong,Xiao Zhang

Batch experiments were conducted to investigate the effect of nitrate on indole degradation characteristics and methanogenesis under mixed denitrification and methanogenesis culture for the first time. The degradation characteristics were studied under various nitrate concentrations. Nitrate was found to facilitate indole degradation and inhibit methane formation, and the optimum concentration was 50 mg L −1 (COD/NO 3 − -N = 12). Balance analyses showed that nitrate mainly affected indole-C, which generated a higher degree of indole mineralization under NO 3 − -N treatment than in the control. Furthermore, GC–MS combined with 13 C-isotope analyses conclusively identified the intermediate metabolites, which included the hydroxylated compounds oxindole and isatin, and the methylated compound 3-methylindole. The results indicated that oxindole did not accumulate and was quickly reduced when nitrate was added, but 3-methylinole, as a recalcitrant material, accumulated without reduction. High-throughput sequencing technology was used to analyse the dynamic microbial community. Results showed that the denitrifying bacterial genera Acinetobacter , Candidimonas and Longilinea accumulated in denitrification stage and decreased in methanogenesis stage, whereas the fermentation genera Alcaligenes and Thermogutta increased in methanogenesis stage. The genera Methanosphaerula and Methanothrix constituted the dominant archaeal communities. The findings obtained in this work may provide a theoretical basis for treatment with N-heterocyclic compounds under mixed culture.

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ACS Applied Nano Materials · 2019 · IF 0

Switching Carbon Nanodots from Single Emission to Dual Emission by One-Step Electrochemical Tailoring in Alkaline Alcohols: Implications for Sensing and Bioimaging

Lihua Shen,Chenxing Wang,Azhar Abbas,Chunxia Yu,Sichun Zhang,Xinrong Zhang,Chengxiao Zhang

Fluorescent carbon nanodots (CNDs) capable of dual emission blue and red light (B-R-CNDs) (460 and 610 nm) have been synthesized by a simple and low cost electrochemical method of discharging indole dissolved in ethanol in the presence of alkali. The presence of alkali played an important role to achieve switching from single blue emission to dual emission (red and blue). The as-synthesized CNDs have been thoroughly characterized by different spectroscopic techniques. Moreover, the origin of the red emission has been investigated by analyzing the intermediate product of CNDs using gas chromatography–mass spectrometry. It was found that 2-naphthaleneamine, an intermediate product of B-R-CNDs, achieves an extended π-conjugated system and heteroatom functional groups to B-R-CNDs, which are synergistically responsible for emission at longer wavelength. Moreover, the alkali-ethanol system played a pivotal role in structural transition from single emission to dual emission, because surface oxidation is caused by hydroxyl radicals produced in the alkaline system. Surface oxidation creates surface defects thereby giving rise to the surface-state-related red emission. The red emission of B-R-CNDs are found highly pH dependent which makes them a potential candidate for application in pH sensing. Moreover, as-prepared B-R-CNDs have been used in full color bioimaging of HepG2 cells and exhibit an accurate mitochondrial-targeting ability.

CAS / MDL: 120-72-9
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RESEARCH ON CHEMICAL INTERMEDIATES · 2019 ·Vol. 45 ·期 10 ·4757-4778 · IF 2.064

Kinetic insights into removal of indole in aqueous solutions by ozonation: operating parameters, modeling and degradation pathways

Jiang Longxin,Wang Chunrong,Chen Xiaoya,Liu Dan,Zhang Qi,Wang Xingmin,Li Haiyan,Sun Moxin

Nitrogenous heterocyclic compounds (NHCs) pose a serious threat to human health and ecosystems, and ozonation has been widely applied in the efficient removal of NHCs in water environments. In the present study, the degradation performance of indole in aqueous solutions was investigated. The second-order rate constants of indole reacting with molecular ozone at pH 2 and ·OH at pH 9 were determined to be 223.24 M −1  s −1 and 12.3 × 10 9  M −1  s −1 , respectively. The effect of different operating parameters both on the mass transfer and chemical kinetics was evaluated during the degradation of indole by ozonation. To attain a better removal performance, a pH value around 9 and a temperature of 35.6 °C were preferred. Additionally, the higher initial ozone concentrations were proved to be beneficial for the enhancement of the removal rate. Compared with synthetic solutions, the removal of indole appeared to be more efficient in real bio-treated coal gasification wastewater. A chemical kinetic model was built based on the rate constants and exposures of O 3 and ·OH, and experimental results demonstrated that the removal rates can be satisfactorily predicted. The relative contributions of O 3 and ·OH measured by the modeling results indicated that the molecular ozone played a dominant role in the reaction system. By further analysis of intermediates with gas chromatography–mass spectrometry (GC–MS), a number of products were detected, and three degradation pathways were tentatively proposed. This work provides a reference for kinetic studies on the treatment of other NHCs using ozone technologies.

CAS / MDL: 75-09-2 120-72-9 67-56-1
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SEPARATION SCIENCE AND TECHNOLOGY · 2019 · IF 1.354

Adsorptive removal of nitrogen compounds from fuel oil by a poly ionic liquid PVIm-PXDC

Chenhua Shu,Lina Wang,Peijun Kong,Meizhu Gao

A poly ionic liquid, poly(1-vinyl imidazole)-p-xylylene dichloride (PVIm-PXDC), was synthesized and used for fuel oil denitrogenation. The structure of PVIm-PXDC was characterized and the denitrogenation performance was investigated. Results indicate that the pseudo-second-order kinetic model and Langmuir model are appropriate to describe the adsorption kinetics and thermodynamics, respectively. The adsorption ability of PVIm-PXDC for different nitrogen compounds follows the order of indole > pyrrole > quinoline > pyridine. The equilibrium adsorption amount decreased about 10% for all the nitrogen compounds after six regeneration cycles and the denitrogenation and regeneration processes have no influence on the structure of PVIm-PXDC.

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RSC Advances · 2018 ·Vol. 8 ·期 40 ·22422-22428 · IF 2.936

Fabrication of a porous β-cyclodextrin-polymer-coated solid-phase microextraction fiber for the simultaneous determination of five contaminants in water using gas chromatography-mass spectrometry

Jiongxiu Pan,Shuming Li,Fuquan Dang,Zhiqi Zhang,Jing Zhang

A novel solid-phase microextraction fiber coated with a porous β-cyclodextrin polymer was developed. The porous β-cyclodextrin polymer cross-linked using tetrafluoroterephthalonitrile, possessed well-distributed pores and the largest surface area among current β-cyclodextrin polymers. Scanning electron microscopy revealed that the coating had a continuous wrinkled and folded structure, which guarantees a sufficient loading capacity for contaminants. The properties of the developed fiber were evaluated using headspace solid-phase microextraction of five contaminants as model analytes coupled with gas chromatography-mass spectrometry. Owing to the advantages of a large surface area and three-dimensional cavities, the novel fiber exhibited excellent operational stability and extraction ability. After optimisation of the extraction conditions, including extraction temperature, extraction time, salt effect, and desorption time, validation of the method with water samples achieved good linearity over a wide range (0.01–120 μg L−1) and low detection limits (0.003–1.600 μg L−1). The single-fiber and fiber-to-fiber repeatabilities were 1.7–11.0% and 1.9–11.0%, respectively. The method was applied to the simultaneous analysis of five analytes with satisfactory recoveries (76.6–106.0% for pond water and 89.0–105.9% for rainwater).

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RSC Advances · 2018 ·Vol. 8 ·期 38 ·21252-21264 · IF 2.936

Synthesis and characterization of novel donor–acceptor type neutral green electrochromic polymers containing an indolo[3,2-b]carbazole donor and diketopyrrolopyrrole acceptor

Yan Zhang,Lingqian Kong,Xiuping Ju,Hongmei Du,Jinsheng Zhao,Yu Xie

Indolocarbazole bearing donor–acceptor type polymers have rarely been reported in the electrochromic field despite them having considerable development in the applications of organic photoelectric devices. In this paper, two novel soluble electrochromic polymers, namely PDTCZ-1 and PDTCZ-2, were prepared by chemical polymerization including indolo[3,2-b]carbazole (IC) units as the donor, diketopyrrolopyrrole (DPP) units as the acceptor and bithiophene units as the bridging group. Through diverse characterization techniques such as cyclic voltammetry (CV), scanning electron microscopy (SEM), UV-vis spectroscopy and thermogravimetric analysis (TGA), it was found that PDTCZ-1 and PDTCZ-2 exhibited saturated green in the neutral state and pale green in the oxidized state with optical band gaps of 1.44 eV and 1.39 eV, respectively, as well as demonstrating fast switching speed, satisfactory coloration efficiency and favorable thermal stability. In addition, the proportion of donors to acceptors definitely exerted an influence on the electrochromic properties of the polymers. As the thiophene/IC/DPP ratio changed from 4/3/1 (PDTCZ-1) to 5/4/1 (PDTCZ-2), meaning an increase of the donor ratio, the polymer showed a reduced onset oxidation potential, decreased optical band gap and different dynamic parameters. The positive results suggest that PDTCZ-1 and PDTCZ-2 could be promising candidates as neutral green electrochromic materials and deserve more attention and penetrating research.

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INSECT MOLECULAR BIOLOGY · 2018 ·Vol. 28 ·期 1 ·23-34 · IF 2.492

An odorant receptor mediates the attractiveness of cis-jasmone to Campoletis chlorideae, the endoparasitoid of Helicoverpa armigera

Y.-L. Sun,J.-F. Dong,C. Ning,P.-P. Ding,L.-Q. Huang,J.-G. Sun,C.-Z. Wang

Parasitic wasps rely on olfaction to locate their hosts in complex chemical environments. Odorant receptors (ORs) function together with well-conserved odorant coreceptors (ORcos) to determine the sensitivity and specificity of olfactory reception. Campoletis chlorideae (Hymenoptera: Ichneunmonidae) is a solitary larval endoparasitoid of the cotton bollworm, Helicoverpa armigera , and some other noctuid species . To understand the molecular basis of C. chlorideae ’s olfactory reception, we sequenced the transcriptome of adult male and female heads (including antennae) and identified 211 OR transcripts, with 95 being putatively full length. The tissue expression profiles, as assessed by reverse-transcription PCR, showed that seven OR s were expressed only or more highly in female antennae. Their functions were analysed using the Xenopu slaevis oocyte expression system and two-electrode voltage-clamp recordings. CchlOR62 was tuned to cis -jasmone, which was attractive to female C. chlorideae adults and H. armigera larvae in the subsequent behavioural assays. Further bioassays using caged plants showed that the parasitism rate of H. armigera larvae by C. chlorideae on cis -jasmone-treated tobacco plants was higher than on the control plants. Thus, cis -jasmone appears to be an important infochemical involved in the interactions of plants, H. armigera and C. chlorideae , and CchlOR62 mediates the attractiveness of cis -jasmone to C. chlorideae .

CAS / MDL: 120-72-9
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Scientific Reports · 2018 ·Vol. 8 ·期 1 ·1-13 · IF 4.122

Synthesis, characterization and in vitro biological evaluation of two matrine derivatives

Cheng Xingan,Ye Jingmin,He Huiqing,Liu Zhanmei,Xu Chunbao (Charles),Wu Bo,Xiong Xialing,Shu Xugang,Jiang Xuhong,Qin Xiangjing

Matrine is a traditional Chinese medicine and botanical pesticide with broad biological activities, including pharmacological and agricultural activities. In present work, two matrine derivatives have been successfully synthesized via introducing indole and cyclohexylamino to 13 position of matrine, respectively, with sophocarpine as starting material, and structurally characterized via infrared spectroscopy(IR), MS, 1 H NMR, 13 C NMR and X-ray crystal diffraction. The results of the in vitro biological activity tests showed that these two matrine derivatives exhibited even better activities against human cancer cells Hela229 and insect cell line Sf9 from Spodoptera frugiperda (J. E. Smith) than that of parent matrine, suggesting that the heterocyclic or cyclic group can dramatically increase the biological activity of matrine. It is worth to mention that 13-indole-matrine could possibly inhibit the growth of insect cells or human cancer cells by inducing cell apoptosis. The results of the present study provide useful information for further structural modifications of these compounds and for exploring new, potent anti-cancer agents and environment friendly pesticides.

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SCIENCE OF THE TOTAL ENVIRONMENT · 2018 · IF 4.61

Preparing coal slurry from coking wastewater to achieve resource utilization: Slurrying mechanism of coking wastewater–coal slurry

Ruikun Wang,Qianqian Ma,Xuemin Ye,Chunxi Li,Zhenghui Zhao

Coking wastewater is used to prepare coal slurry, which can be used as combustion and gasification fuel. This promising technology simultaneously achieves resource utilization and wastewater management . Slurrying properties are essential to the industrial application of coal slurry. These properties are considerably influenced by coal surface properties and the adsorption of an additive by coal. In this study, the effects of the internal components (e.g., phenol, ammonia nitrogen, and metal ions) of coking wastewater on the adsorption of an additive by coal and on coal surface properties were measured. Results showed that the competitive adsorption between phenol and the additive reduced the amount of additive adsorbed on coal. However, phenol acted as an additive to improve the wettability of coal particles. Cations (Ca 2+ , NH 4 + , and Na + ) adversely affected the slurrying because they weakened the negative charges of coal. Furthermore, a large amount of water was adsorbed due to the ionic bonding effects, thereby reducing the free water in the coal slurry system. The maximum slurrying concentration of CWCS was 0.8 percentage points higher than that of CWS, suggesting that coking wastewater enhanced the slurrying capability of the coal slurry by integrating the various effects induced by the different internal components.

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FUEL · 2019 · IF 5.128

Extractive removal of both basic and non-basic nitrogens from fuel oil by dicarboxyl-modified polyethylene glycol: Performance and mechanism

Xingmao Jiang,Shuang Zhu,Jiajun Gao,Yaqian Yu,Chunyan Xiong,Chunxi Li,Weimin Yang

Polyethylene glycol [PEG, H(OCH 2 CH 2 ) n OH] like PEG-600, a green extractant for organic N-compounds in fuel oil, was very active for non-basic nitrogens but not effective for basic ones. Modification of PEG that replaced –OH group with –OCH 2 COOH group can produce HOOCCH 2 (OCH 2 CH 2 ) n OCH 2 COOH (dcPEG). For denitrogenation, dcPEG-600 was highly effective for both basic and non-basic nitrogens. N-distribution coefficient [ D N , (μg N ·g dcPEG −1 )/(μg N ·g oil −1 )] of dcPEG-600 to n -octane can reach as high as 200 for indole, 92.6 for pyrrole, 42.0 for quinoline, and 81.5 for pyridine, respectively. Besides, denitrogenation selectivity of dcPEG-600 to toluene ( D N / D toluene ) can amount to 462 for indole, 230 for pyrrole, 146 for quinoline, and 366 for pyridine, respectively. The high performance was ascribed to contribution of active O atom on ether group and active H atom on –COOH group. The active O atom (Lewis basic site) formed H-bond with the non-basic nitrogen (Brønsted acid). The active H atom (Brønsted acidic site) not only interacted with the basic one (Lewis base) but also brought in the good selectivity. Moreover, dcPEG-600 was still effective for real oil and could be recycled for several times without the denitrogenation performance significantly decreasing.

CAS / MDL: 120-72-9
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JOURNAL OF APPLIED POLYMER SCIENCE · 2014 ·Vol. 132 ·期 15 · IF 1.64

Optimal design of an imprinted preassembled system by quantum chemical calculations and preparation of a surface-imprinted material for the selective removal of quinoline

Wenming Yang,Pengfei Ma,Ting Fan,Zhiping Zhou,Hong Liu,Wanzhen Xu

In this study, we examined the rational preparation of molecularly imprinted polymers (MIPs) for the selective removal of quinoline from octane. Before the preparation, density functional theory, as one of the methods of quantum chemical calculation, was used for the simulation of a quinoline-imprinted preassembly system. Methacrylic acid turned out to be the more suitable monomer for quinoline compared with acrylamide, and different template–monomer ratios, including 1:1, 1:2, and 1:3, were studied and are discussed. On the basis of the result of molecular simulation, quinoline-imprinted polymers were prepared with a combination of surface imprinting and living polymerization. The prepared quinoline–MIPs were characterized and used as selective adsorbents for batch-mode binding experiments. The fitting result of the adsorption data indicates that the adsorption kinetics and adsorption isotherms of the quinoline-imprinted polymers fit well a pseudo-second-order kinetics model and the Freundlich model, respectively. A selective recognition ability was demonstrated by equilibrium binding analysis. This study will provide needful guidance and a theoretical basis for the preparation of imprinted materials in the field of industrial denitrification. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132 , 41730.

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