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Fast Response Fluorescent Probe with a Large Stokes Shift for thiophenol Detection in Water Samples and Cell Imaging

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Journal of Analysis and Testing 2023年第1期7卷 69-78页

作者： Jinjie You Hua Liu Qiaofen Pan Aili Sun Zeming Zhang Xizhi Shi State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products School of Marine SciencesNingbo UniversityNingbo 315211China College of Food and Pharmaceutical Sciences Ningbo UniversityNingbo 315211China

Herein,the 2,4-dinitrophenyl functional group acting as the thiophenol reactive site was introduced into a carbazole-chalcone fluorophore to synthesize probe-CCF2,which could result in a remarkable increase in fluorescence when reacting with thiophenols.The selectivity and accuracy of probe-CCF2 were investigated with thiophenols,hydrosulphide salt,aliphatic thiols,glutathione,cysteine,anions and metal cations.Probe-CCF2 exhibited a detection limit of 37 nmol/L(R^(2)=0.9951),a remarkable Stokes shift of approximately 130 nm,and a brief response time of 9 min with a remarkable increase in fluorescence of 90-fold.Probe-CCF2 was applied for thiophenol detection in water samples and imaging in living cells successfully,with high sensitivity and excellent selectivity.

关键词： thiophenol Large Stokes shift Fluorescent probe Water sample Cell imaging

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A NIR fluorescent probe for imaging thiophenol in the living system and revealing thiophenol-induced oxidative stress

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中国化学快报:英文版 2023年第8期34卷 497-501页

作者： Zesi Wang Jiao Li Jiao Chen Zifeng Cao Hui Li Yaopeng Cao Quanquan Li Mengyao She Ping Liu Shengyong Zhang Jianli Li Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education College of Chemistry&Materials ScienceNorthwest UniversityXi’an 710127China Key Laboratory of Resource Biology and Biotechnology in Western China Ministry of EducationBiomedicine Key Laboratory of Shaanxi ProvinceLab of Tissue EngineeringCollege of Life SciencesNorthwest UniversityXi’an 710127China Shaanxi Key Laboratory of Earth Surface System and Environmental Carrying Capacity College of Urban and Environmental SciencesNorthwest UniversityXi’an 710127China

thiophenol(PhSH)is an important raw material for organic synthesis,while its high toxicity to organisms makes it an environmental pollutant.Therefore,it is crucial to accurately detect PhSH and explore its metabolic process in the living system.Herein,a near-infrared(NIR)fluorescent probe TEM-FB was developed for sensing PhSH with a turn-on fluorescent signal at 719nm and a large Stokes shift(198 nm)based on generating the intramolecular charge transfer(ICT)process.TEM-FB shows high specificity and significant sensitivity towards PhSH(detection limit:10 nmol/L)via the aromatic nucleophilic substitution mechanism.Furthermore,it was successfully applied to image PhSH in multiple cell lines and in zebrafish.Notably,we revealed the oxidative stress process caused by PhSH and demonstrated that the hydrogen peroxide(H_(2)O_(2))in cells would alleviate the poisonousness from exogenous PhSH for the first time.This work provides a promising bioimaging tool for monitoring PhSH in living systems and visualizing the process of oxidative stress induced by PhSH.

关键词： Fluorescent probe Near-infrared Oxidative stress thiophenol Large Stokes shift Dicyanoisophorone

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A BODIPY-based Fluorescent Probe for thiophenol

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Chinese Journal of Chemistry 2018年第2期36卷 119-123页

作者： Dongxiang Zhang Ning Xu Liman Xian Haoying Ge Jiangli Fan Jianjun Du Xiaojun Peng State Key Laboratory of Fine Chemicals Dalian University of Technology Dalian 116024 China

thiophenol has been listed as one of the main sources of pollution. Sensitive probes for thiophenol are very significant. Herein, a BODIPY-based fluorescent probe, named BDP, for poisonous thiophenol detection has been reported. BDP shows rapid response （15 s） and clear fluorescence enhancement （30 folds） to thiophenol in solution. The intensity of fluorescence and concentration of thiophenol have a good linear relationship. The detection limit is as low as 13.6 nmol·L^-1： BDP is stable towards pH and light radiation. Cell experiments demonstrate that BDP has good cell membrane penetrability, low cell toxicity and excellent imaging properties in living cells. Therefore, BDP has significant value on the detection of thiophenol in solution and in living cell.

关键词： thiophenol BODIPY fluorescent probe cell imaging

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Fluorescent Turn-on Probe Based on Napthalimide Fused Triphenylamine Unit for Quickly Detecting thiophenol in Aqueous Solution

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Chemical Research in Chinese Universities 2019年第6期35卷 990-996页

作者： SUN Jiaojiao CAO Jian CHENG Hailong WANG Jincheng WANG Shuxin School of Chemistry atui Chemical Engineering Shanghai University of Engineering ScienceShanghai 201620P.R.China State Key Laboratory for Modification of Chemical Fibers and Polymer Materials College of Materials Science and EngineeringDonghua UniversityShanghai 201620P.R.China

A novel molecular probe system(NapTpa-dnbs)was prepared based on the chromophore napthalimide fused triphenylamine unit.NapTpa-dnbs was tuned to absorb a large fraction of UV and near-infrared radiation.The turn-on fluorescent response of NapTpa-dnbs to thiophenol caused an increased fluorescent emission by a factor of 11.5 at 597 nm in a PBS buffer solution.The photoinduced electron transform(PET)process of the probe became less feasible with the addition of thiophenol than that of the free probe.NapTpa-dnbs demonstrated high selective and sensitive detection toward thiophenol with respect to other competitive amine acids.The detection limit was determined to be 2.03×10^?7 mol/L thiophenol.The sensing process is rapid(3 min).NapTpa-dnbs can accurately detect the thiophenol with a qualified recovery in real water samples.NapTpa-dnbs on test strips can detect the thiophenol vapour in the atmosphere.

关键词： Napthalimide Probe thiophenol Tum-on Fluorescent

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Syntheses and Crystal Structures of Two New Iron-sulfur Carbonyl Complexes: [Fe_2(SC_6H_4Cl)_2(CO)_6]·0.5(Et_2O) and [Fe_3(SC_6H_4NH_2)_6(CO)_6]·2(MeOH)

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Chinese Journal of Structural Chemistry 2006年第3期25卷 326-332页

作者：马成丙陈昌能刘秋田 State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter The Chinese Academy of Sciences

Two new iron-sulfur carbonyl complexes, [Fe2（SC6H4Cl）2（CO）6]·0.5（Et2O） 1 and [Fe3（SC6H4NH2）6（CO）6]·2（MeOH） 2, have been prepared and characterized by elemental analysis, IR spectra and single-crystal X-ray diffraction. Crystal data for 1： monoclinic, C2/c, a = 18.4439（8）, b = 11.0999（5）, c = 25.1830（10）A°, β = 97.0370（10）°, V = 5116.8（4） A°^3, Z = 8, C20H13Cl2Fe2O6.50S2, Mr = 604.02, Dc = 1.568 g/cm^3, μ = 1.540 mm^-1, F（000） = 2424, the final R = 0.0545 and wR = 0.1454 for 3443 observed reflections with I 〉 2σ（I）; 2： monoclinic, P21/n, a = 12.350, b = 26.3050（11）, c = 16.057A°, β = 97.891 （3）°, V = 5166.9（2）A°^3, Z = 4, C44H44Fe3N6O8S6, Mr = 1144.76, Dc = 1.472 g/cm^3, μ = 1.128 mm^-1, F（000） = 2352, the final R = 0.0442 and wR = 0.1197 for 7978 observed reflections with I 〉 2σ（I）. Complex 1 contains one iron dimer, in which two tricarbonyliron（Ⅰ） fragments are bridged together by two 4-chlorophenylthiolate ligands, whereas complex 2 contains a linear tri-iron cluster, in which two terminal tricarbonyliron（Ⅱ） fragments and the central Fe（Ⅱ） atom are linked together by six 4-aminophenylthiolate bridging ligands.

关键词： iron-sulfur carbonyl complex thiophenol synthesis crystal structure

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Synthesis and Free-Radical Thiilation (Addition of thiophenols) of Unsaturated Cyclic Acetals

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Journal of Chemistry and Chemical Engineering 2019年第2期13卷 76-81页

作者： Farida Yusifli Gafar Ramazanov Abasgulu Guliyev Sumgait State University 124 S. Vurgun Sumgait Az5004 Azerbaijan Institute of Polymer Materials of Azerbaijan National Academy of Sciences 124 S.Vurgun Sumgait Az5004 Azerbaijan

The synthesis of a series of unsaturated 4-methylene-1,3-dioxolanes has been realized and the addition of thiophenol to the synthesized compounds in the presence of radical initiators has been carried out. It has been established the behavior of the addition reaction both with opening of dioxolane cycle and without it. The influence of nature of substituents of С2-carbon atom of dioxolane cycle, ratio of the initial reagents and temperature on direction of the addition reaction has been studied. The adducts obtained as a result of the addition reaction have a linear and cyclic structure, which have been established by data of the chemical and spectral analyses. It has been found that the ratio dioxolane compound: thiophenol, reaction temperature and nature of the functional substituent influences on quantity of these adducts.

关键词： Methylenedioxolane thiophenol adduct thiilation

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