CN111116629A - 一种苯并噻唑类氟离子荧光探针 - Google Patents

一种苯并噻唑类氟离子荧光探针 Download PDF

Info

Publication number
CN111116629A
CN111116629A CN201811283045.9A CN201811283045A CN111116629A CN 111116629 A CN111116629 A CN 111116629A CN 201811283045 A CN201811283045 A CN 201811283045A CN 111116629 A CN111116629 A CN 111116629A
Authority
CN
China
Prior art keywords
fluorescent probe
fluorine
benzothiazole
fluoride ion
ions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201811283045.9A
Other languages
English (en)
Inventor
杨绍祥
田红玉
刘永国
孙宝国
武小明
王皓
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beijing Technology and Business University
Original Assignee
Beijing Technology and Business University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beijing Technology and Business University filed Critical Beijing Technology and Business University
Priority to CN201811283045.9A priority Critical patent/CN111116629A/zh
Publication of CN111116629A publication Critical patent/CN111116629A/zh
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Immunology (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

本发明公开了一种检测氟离子的苯并噻唑类荧光探针，具体化学结构式如下所示：

Description

一种苯并噻唑类氟离子荧光探针
技术领域
本发明涉及一种苯并噻唑类氟离子荧光探针以及其在检测氟离子中的应用。
背景技术
氟是一种人体必需的微量元素，与人体健康密切相关，人体各组织中都含有氟，但主要积聚在牙齿和骨骼中。在天然饮用水和食物中都有低浓度的氟离子存在，而地下水中的氟含量更高。海水中氟离子含量为1.2-1.5ppm，淡水中为0.01-0.3ppm。适当的氟是人体所必需的，过量的氟对人体有危害，过量氟的摄入可引起神经元功能异常，血脑屏障被破坏，干扰正常的脑组织代谢，进而对脑功能产生影响；对人体内分泌激素水平以及内分泌器官如甲状腺、垂体、性腺等均会产生影响，且对生殖系统毒性作用和不育之间存在明显关系。氟化钠对人的致死量为6-12克，饮用水含2.4-5毫克/升则可出现氟骨症。人体摄入氟的途径有饮用水、食物、空气、含氟日用品。饮用水是最重要的摄入氟途径，全世界不同地区对饮用水中氟的标准不同主要是因为氟作为一种地区性分布明显的元素，各国人群的敏感性与各地区氟含量的差异导致世界不同地区都在根据实际制定相应的标准。我国规定饮用水中氟浓度小于1.0毫克/升。氟化物的测定方法有氟试剂比色法、茜素磺酸锆比色法和离子选择电极法、离子色谱法等。
有机小分子荧光探针检测法由于其具有成本低廉、检测快速、操作简便、灵敏高、选择性好等优点，是一种非常有效的检测方法。因此，以荧光探针作为检测工具，测定氟离子的含量，对食品安全研究具有重要的意义。
发明内容
本发明目的是提供一种检测氟离子的荧光探针，它适于在药品、食品、水等样品中检测氟离子。
更具体的是，本发明涉及一种检测氟离子的荧光探针，它通过下式表示：
Figure BSA0000172983560000011
附图说明
图1是在二甲基亚砜溶液中，随着不同浓度氟离子的加入，本发明的荧光探针(10μM)的荧光强度变化。嵌入图：氟离子的浓度。
图2是在二甲基亚砜溶液中，本发明的荧光探针(10μM)荧光强度随着氟离子浓度变化的标准曲线。
图3是254nm紫外灯下，本发明的荧光探针试纸浸染不同浓度氟离子溶液(0，1，2，3，4，5，6μM)后试纸发光强度变化情况。
具体实施方式
实施例1.检测氟离子的荧光探针的制备
合成路线如下式所示：
Figure BSA0000172983560000021
化合物1(0.999g，3.609mmo)、化合物2(0.543g，3.609mmol)、4-二甲氨基吡啶(0.120g，1.083mmol)、二氯甲烷(20mL)加入到100mL三口烧瓶中，搅拌升温至80℃，反应8h，冷却至室温，抽滤，滤液真空旋蒸，柱层析得固体化合物3。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，DMSO)，δ(ppm)：8.54(s，1H)，8.15(dd，J＝13.7，5.1Hz，2H)，7.95-7.77(m，3H)，7.52(t，J＝7.1Hz，1H)，7.40(t，J＝7.1Hz，1H)，7.23(d，J＝2.1Hz，1H)，7.15(dd，J＝8.8，2.4Hz，1H)，1.04(s，9H)，0.28(s，6H)；13C NMR(75MHz，DMSO)，δ(ppm)：167.47，154.15，152.94，135.15，133.84，129.45，127.85，126.53，125.40，124.13，123.78，122.14，121.98，120.60，113.96，28.69，28.35，24.69，21.68，17.28.
实施例2.检测氟离子的荧光探针试纸的制备
将滤纸剪裁成1cm×1cm大小的正方形试纸，并将其浸泡于1mM本发明荧光探针溶液(DMSO溶剂)中，得本发明的荧光探针试纸。
如图1所示，本发明荧光探针为比率型荧光探针，512nm发射峰强度逐渐降低，406nm发射峰强度逐渐增强，依据该变化可作出该荧光探针(10μM)荧光强度(F512nm/F406nm)随着氟离子浓度变化的标准曲线，标准曲线如图2所示，通过该标准曲线的建立，本发明的荧光探针可用于氟离子的定量检测。如图3所示，本发明的荧光探针试纸在低浓度氟离子作用下无发光现象，当氟离子浓度达到4μM时，本发明的试纸有发光现象，当氟离子浓度增加到5μM(0.95mg/L)时，发光明显。本发明的荧光探针可用于氟离子的定性及半定量检测。

Claims (1)

1.一种检测氟离子的苯并噻唑类荧光探针，具体化学结构式如下所示：
Figure FSA0000172983550000011
CN201811283045.9A 2018-10-31 2018-10-31 一种苯并噻唑类氟离子荧光探针 Pending CN111116629A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811283045.9A CN111116629A (zh) 2018-10-31 2018-10-31 一种苯并噻唑类氟离子荧光探针

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811283045.9A CN111116629A (zh) 2018-10-31 2018-10-31 一种苯并噻唑类氟离子荧光探针

Publications (1)

Publication Number Publication Date
CN111116629A true CN111116629A (zh) 2020-05-08

Family

ID=70485011

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811283045.9A Pending CN111116629A (zh) 2018-10-31 2018-10-31 一种苯并噻唑类氟离子荧光探针

Country Status (1)

Country Link
CN (1) CN111116629A (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102250134A (zh) * 2010-05-21 2011-11-23 中国科学院化学研究所 一种识别氟离子的荧光探针及其制备方法和用途
CN104449677A (zh) * 2014-12-29 2015-03-25 大连理工常熟研究院有限公司 一种用于识别氟离子的特异性荧光探针及其应用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102250134A (zh) * 2010-05-21 2011-11-23 中国科学院化学研究所 一种识别氟离子的荧光探针及其制备方法和用途
CN104449677A (zh) * 2014-12-29 2015-03-25 大连理工常熟研究院有限公司 一种用于识别氟离子的特异性荧光探针及其应用

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
SHYAMAPROSAD GOSWAMI ET AL: "A colorimetric and ratiometric fluorescent turn-on fluoride chemodosimeter and application in live cell imaging: high selectivity via specific SiAO cleavage in semi aqueous media and prompt recovery of ESIPT along with the X-ray structures", 《TETRAHEDRON LETTERS》 *
WEI HU ET AL: "A Ratiometric Two-photon Fluorescent Probe for fluoride ions imaging in Living Cells and Zebrafish", 《ANALYST》 *
XIAOMING WU ET AL: "Highly Sensitive Ratiometric Fluorescent Paper Sensors for the Detection of Fluoride Ions", 《ACS OMEGA》 *
王少静 等: "新型香豆素类氟离子荧光探针的合成及细胞成像研究", 《化学学报》 *

Similar Documents

Publication Publication Date Title
Golet et al. Trace determination of fluoroquinolone antibacterial agents in urban wastewater by solid-phase extraction and liquid chromatography with fluorescence detection
King et al. The clinical biochemistry of aluminum
Pourreza et al. Solid phase extraction of cadmium on 2-mercaptobenzothiazole loaded on sulfur powder in the medium of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and cold vapor generation–atomic absorption spectrometric determination
CN108169189B (zh) 一种响应二氧化硫/亚硫酸（氢）盐的比率荧光探针
JP6258355B2 (ja) 水中の亜硝酸イオンの選択的な検出のための新規アザｂｏｄｉｐｙ化合物及びその調製方法
Buratti et al. Aluminum determination in biological fluids and dialysis concentrates via chelation with 8-hydroxyquinoline and solvent extraction/fluorimetry
Scully et al. Derivatization of organic and inorganic N-chloramines for high-performance liquid chromatography analysis of chlorinated water
Zu et al. Ultra-trace determination of methylmercuy in seafood by atomic fluorescence spectrometry coupled with electrochemical cold vapor generation
Wang et al. A highly sensitive and selective spectrofluorimetric method for the determination of nitrite in food products
CN106198518B (zh) 一种铜离子快速检测试纸及其制备方法
CN110646272A (zh) 一种亲水性离子液体的纯化方法
CN111116629A (zh) 一种苯并噻唑类氟离子荧光探针
Barve et al. Fluorescein tri-aldehyde promotes the selective detection of homocysteine
CN109370573B (zh) 一种二价汞离子和温度检测的荧光探针、制备方法及其应用
Adams et al. Residue Determination, Spectrophotofluorometric Method for Guthion Residues in Milk and Animal Tissues
CN111116630A (zh) 一种萘环类氟离子荧光探针
CN112442358B (zh) 一种苯并噻唑类汞离子荧光探针
de Blas et al. Determination and speciation of arsenic in human urine by ion-exchange chromatography/flow injection analysis with hydride generation/atomic absorption spectroscopy
CN112442357B (zh) 一种双反应位点荧光探针
Collecchi et al. The distribution of arsenic and cobalt in patients with laryngeal carcinoma
Hosseini et al. Nano Analysis in Biochemistry: In Vitro Separation and Determination of Aluminium in Blood of Dialysis Patients Based on Graphene Oxide Nanoparticles Dispersed to Ionic Liquid
Balcerzak Biomonitoring of human exposure to fluorine
Abou-El-Sherbini et al. A new selective chromogenic reagent for the spectrophotometric determination of thallium (I) and (III) and its separation using flotation and the solid-phase extraction on polyurethane foam
CN111072650A (zh) 一种苯并噻唑类硫化氢荧光探针
CN112441954A (zh) 一种双识别位点汞离子荧光探针

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20200508