CN107021953A - 一种香豆素荧光探针和制备方法及其在检测次氯酸根离子上的应用 - Google Patents

一种香豆素荧光探针和制备方法及其在检测次氯酸根离子上的应用 Download PDF

Info

Publication number
CN107021953A
CN107021953A CN201710338890.0A CN201710338890A CN107021953A CN 107021953 A CN107021953 A CN 107021953A CN 201710338890 A CN201710338890 A CN 201710338890A CN 107021953 A CN107021953 A CN 107021953A
Authority
CN
China
Prior art keywords
fluorescent probe
hypochlorite ion
coumarin fluorescent
probe
detection
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.)
Granted
Application number
CN201710338890.0A
Other languages
English (en)
Other versions
CN107021953B (zh
Inventor
但飞君
鲁茜
刘瑶
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.)
China Three Gorges University CTGU
Original Assignee
China Three Gorges University CTGU
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 China Three Gorges University CTGU filed Critical China Three Gorges University CTGU
Priority to CN201710338890.0A priority Critical patent/CN107021953B/zh
Publication of CN107021953A publication Critical patent/CN107021953A/zh
Application granted granted Critical
Publication of CN107021953B publication Critical patent/CN107021953B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • 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
    • 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
    • G01N21/6402—Atomic fluorescence; Laser induced fluorescence
    • 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"
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • G01N2021/6417—Spectrofluorimetric devices
    • 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"
    • G01N2021/6443—Fluorimetric titration

Landscapes

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

Abstract

本发明提供了一个香豆素的荧光探针，制备方法及其在次氯酸根离子检测上的应用。具体涉及的探针为3‑[2‑[8‑(1H‑苯并咪唑‑2‑基)喹啉‑2‑基]乙烯基]‑7‑二乙胺基香豆素。它是以2‑甲基‑8‑(1H‑苯并咪唑‑2‑基)喹啉和3‑甲酰基‑7‑二乙胺基香豆素为原料经缩合制备得到的。次氯酸根离子与探针C作用后，裸眼可见C溶液由橘黄色变成淡黄色，在365nm紫外灯下，溶液由橘黄色荧光变成亮黄色荧光。紫外可见分光光度法检测次氯酸根离子的最低检测限4.6698×10‑8mol/L，荧光分光光度法检测次氯酸根离子的最低检测限为2.1037×10‑8mol/L。本发明可用紫外可见分光光度法和荧光分光光度法对不同来源的样品微/痕量氯酸根离子的定量检测。

Description

一种香豆素荧光探针和制备方法及其在检测次氯酸根离子上 的应用
技术领域
本发明涉及离子分析检测技术领域，特指一种次氯酸根离子显色剂及其制备方法和应用。
背景技术
作为生命内重要的活性氧之一，次氯酸根离子参与了生命体众多的生理过程，是正常的细胞代谢副产品之一，在生命活动中发挥着重要的作用。另一方面，次卤酸盐作为一种有效的抗菌剂和漂白剂也被广泛应用于日常生活中。但是过量的次氯酸根离子也会导致组织损伤，并引发系列疾病，如心血管疾病、肾病、肺损伤、关节炎、哮喘，甚至癌症等。由于次氯酸根离子在环境和生物样品广泛存在，因此检测环境(水样)和生命体系中的次氯酸含量越来越引起人们的关注。
目前已建立的检测次氯酸根离子的方法包括碘量滴定法、电化学法、分光光度法和荧光分析法。近年来，由于科学技术的不断发展，以紫外可见分光光度法、荧光分分光光度法因所需仪器相对简单、选择性和灵敏度高、检测范围广、响应时间快速，并且检测过程对样品没有破坏，对细胞危害小等特点在环境、生命、医药等领域的应用越来越广泛。
比率型的探针是在两个不同波长下测定荧光强度(或吸光度)，并以其比值作为测定信号，因此其可以通过内置的校正消除环境因素、光源稳定性、探针浓度等因素的干扰，从而使检测结果不受光源强度、仪器灵敏度、探针浓度、环境因素的影响，克服了传统荧光探针所存在的缺点，故比率型荧光探针分子可以得到更精确的检测结果，进而提高检测方法的灵敏度和更宽的动态响应范围，受到了越来越多的关注。此外，基于比色基的紫外可见光、荧光检测能实现次氯酸根离子含量的原位检测和实时监控，在环境、生命、医药等领域有良好的应用前景。
发明内容
本发明的目的在于提供一种比率型检测次氯酸根离子的探针C，该探针为3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素。
本发明的另一目的在于提供一种比率型检测次氯酸根离子的荧光探针C的制备方法，包括如下步骤：向两口瓶中加入2-甲基-8-苯并咪唑基喹啉和3-甲酰基-7-二乙胺基香豆素，装上分水器，滴加正丁醇，加热搅拌使固体溶解，加入催化剂，搅拌回流反应；反应结束后纯化得到探针C。
所述的制备方法中2-甲基-8-(1H-苯并咪唑-2-基)喹啉和3-甲酰基-7-二乙胺基香豆素的摩尔比为1：0.8～3。
所述的溶剂为极性溶剂，包括乙醇或丙醇或正丁醇或戊醇，优选正丁醇。
所述的催化剂为碱和酸，其中碱为哌啶或吡啶或N,N-二甲基吡啶或碳酸钠或碳酸钾，酸为乙酸或乙酸酐或硫酸，优选哌啶和乙酸，且哌啶和乙酸的摩尔比为1：0.5～4。
所述的纯化方法为打浆洗涤法，滤饼用二氯甲烷溶解，加入醇包括甲醇或乙醇或丙醇或正丁醇，优选乙醇，析出固体。
所述的纯化步骤为硅胶柱层析，洗脱液为石油醚与乙酸乙酯的混合溶液，石油醚与乙酸乙酯的体积比为0-1：3-100。
本发明的又一目的在于比率型检测次氯酸根离子的探针C在次卤酸根离子分析检测上作为显色指示剂上的应用。
次氯酸根离子存在时，探针C溶液由橘黄色变成淡黄色。于此同时，在365nm紫外灯下，探针分子溶液由橘黄色荧光变成亮黄色荧光。可用于定性检测次氯酸根离子，包括其盐及酸中的次卤酸根离子。
随着次氯酸根离子的浓度增加，探针C最大吸收波长460nm减弱。于此同时，其570nm发射峰逐渐减弱，在470nm出现新的发射峰并逐渐增强。该探针对其他阴离子(S2O8 2-，SO4 2-，P2O7 4-，HPO4 2-，NO3 -，SO3 2-，CO3 2-，ClO-，Cl-，F-，S2-)的抗干扰能力强，是一种比率型高灵敏的荧光探针；该探针分子对次氯酸根离子紫外可见分光光度法最低检测限4.6698×10- 8mol/L，荧光分光光度法最低检测限为2.1037×10-8mol/L。故本探针可用于紫外可见分光光度法和和荧光分光光度法对次氯酸根离子包括其盐及酸中的次卤酸根离子的定量检测。
本发明有益效果：
与现有技术相比本发明的优点：本发明的次氯酸根离子光谱探针合成方法简单，易于生产；与次氯酸根离子反应迅速，对次氯酸根离子选择性好，响应快，灵敏度高；并且检测过程快速、结果准确，应用前景广泛等优点，可用于复杂样品的实时和快速定性测量，也能用于不同来源的样品微/痕量的定性、定量检测。
附图说明
图1为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)检测次氯酸根离子的吸收光谱。
图2为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)检测次氯酸根离子的紫外可见光吸收随次氯酸浓度变化线性关系图。
图3为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)的荧光光谱。
图4为为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)检测次氯酸根离子的荧光发射比率(F470nm/F570nm)随次氯酸根离子浓度变化线性关系图。
图5为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)对不同阴离子荧光选择性测试的荧光光谱。
图6为实施例1所制备的3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)在不同阴离子时对次氯酸根离子测定影响的荧光法光谱。
具体实施方式
下面结合实施例来进一步说明本发明，但本发明要求保护的范围并不局限于实施例表述的范围。
实施例1
苯并咪唑取代的喹啉衍生物3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素(C)(次氯酸根离子探针)
向50mL两口瓶中加入0.5193g(2.0mmol)2-甲基-8-苯并咪唑基喹啉，0.8021g(3.2mmol)3-甲酰基-7-二乙胺基香豆素，装上分水器，滴加10mL正丁醇，加热搅拌使固体溶解，加入1.3mL哌啶，0.17mL冰醋酸，回流8h至2-甲基-8-苯并咪唑基喹啉反应完全(TLC跟踪)，冷却至室温，抽滤，乙醇洗涤，干燥，得0.5103g红色固体，即3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素，产率53.06％，m.p.:250～252℃。1HNMR(400MHz,CDCl3):δ13.78(s,1H),9.06(d,J＝7.5Hz,1H),8.29–7.99(m,1H),7.97-7.50(m,7H),7.42–7.28(m,3H),6.59(dd,J＝8.8,2.3Hz,1H),6.47(d,J＝2.1Hz,1H),3.42(d,J＝7.1Hz,4H),1.24(t,J＝7.1Hz,6H).ESI-MS,m/Z(％):487.2705(M+1，100)。
实施例2
(1)测试液的配制：
在10mL样品瓶中，加入1.0mL双蒸水(pH＝7.40)，再加入0.01mol/L现配置的ClO-标准溶液(200μL，20eq)，再加入9.0mL乙腈，混匀；最后加入100μL探针C的THF溶液(10-3mol/L)，再次混匀。放置1小时后，于380nm为激发波长，测定紫外吸收和荧光发射。如上的操作，不加入阴离子溶液，即为空白试液的配制。测定紫外吸收和荧光发射。
(2)紫外光谱和荧光光谱测试：
探针C的空白试液在460nm处有较强最大吸收峰；当存在次氯酸根离子时，460nm处的吸收显著减弱，见图1。探针C的空白试液在570nm有较强的荧光发射峰，加入次氯酸根离子后，570nm荧光减弱，470nm出现新的发射峰，见图3。
(3)检测次氯酸根离子的紫外可见光滴定实验：
线性拟合得出检测次氯酸根离子的剂量曲线，见图2。根据最低检出限公式(LOD＝3σ/b)计算，在紫外可见分光光度法探针C对次氯酸根离子的LOD为：4.6698×10-8mol/L。
(4)检测次氯酸根离子的荧光滴定实验：
线性拟合得出检测次氯酸根离子的荧光强度F460nm/F570nm-剂量曲线，见图4。根据最低检出限公式(LOD＝3σ/b)计算，在荧光分光光度法探针C对次氯酸根离子的LOD为：2.1037×10-8mol/L。
(5)离子选择性实验：
当同样浓度的各种阴离子分别与探针C作用时，唯有次氯酸根离子能引起探针C在470nm荧光强度明显增强。其他阴离子与探针C作用时，相比较于探针C的空白试液，其在470nm处荧光强度无明显变化。这表明，就荧光分光光度法而言，探针C对次氯酸根离子的传感具有高度的特异性选择。见图5。
(6)共存离子对次氯酸根离子测定的影响：
为进一步考察探针C对次氯酸根离子传感的选择性，尝试了阴离子与次氯酸根离子共存时对体系荧光强度的影响。次氯酸根离子图6与同等浓度各种阴离子共存时体系的荧光发射。各阴离子分别为：S2O8 2-，SO4 2-，P2O7 4-，HPO4 2-，NO3 -，SO3 2-，CO3 2-，ClO-，Cl-，F-，S2-。由图6可见，其他阴离子对次氯酸根离子的检测几乎无影响。
上述的实施例仅为本发明的优选技术方案，而不应视为对于本发明的限制，本申请中的实施例及实施例中的特征在不冲突的情况下，可以相互任意组合。本发明的保护范围应以权利要求记载的技术方案，包括权利要求记载的技术方案中技术特征的等同替换方案为保护范围。即在此范围内的等同替换改进，也在本发明的保护范围之内。

Claims (10)

1.一种香豆素荧光探针，其特征在于，该探针为3-[2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基]-7-二乙胺基香豆素，以下简称为探针C，具体结构式如下：
a)
2.权利要求1所述的香豆素荧光探针的制备方法，其特征在于，包括如下步骤：向两口瓶中加入2-甲基-8-苯并咪唑基喹啉和3-甲酰基-7-二乙胺基香豆素，装上分水器，滴加正丁醇，加热搅拌使固体溶解，加入催化剂，120℃搅拌回流反应6-10h；反应结束后，抽滤、纯化后得到探针C。
3.权利要求2所述的香豆素荧光探针的制备方法，其特征在于，2-甲基-8-(1H-苯并咪唑-2-基)喹啉和3-甲酰基-7-二乙胺基香豆素的摩尔比为1：0.8～3。
4.权利要求2所述的香豆素荧光探针的制备方法，其特征在于，所述的极性溶剂包括乙醇或丙醇或正丁醇或戊醇，优选正丁醇。
5.权利要求2所述的香豆素荧光探针的制备方法，其特征在于，所述的催化剂为碱和酸，其中碱为哌啶或吡啶或N,N-二甲基吡啶或碳酸钠或碳酸钾，酸为乙酸或乙酸酐或硫酸，优选哌啶和乙酸，且哌啶和乙酸的摩尔比为1：0.5～4。
6.权利要求2所述的香豆素荧光探针的纯化方法，其特征在于，可用打浆洗涤法和柱层析法。
7.权利要求6所述的香豆素荧光探针的纯化方法中打浆洗涤法，其特征在于：滤饼用二氯甲烷溶解，加入醇包括甲醇或乙醇或丙醇或正丁醇，优选乙醇，析出固体。
8.权利要求6所述的香豆素荧光探针的纯化方法中的柱层析，其特征在于，所述的硅胶柱层析，洗脱液为石油醚和/或乙酸乙酯的混合溶液，石油醚与乙酸乙酯的体积比为0-1：3-100。
9.权利要求1所述的香豆素荧光探针在定性和定量检测次氯酸根离子上的应用。
10.权利要求9所述的香豆素荧光探针在定性检测次氯酸根离子上的应用，其特征在于：自然光及365nm紫外灯下观察颜色变化。
CN201710338890.0A 2017-05-15 2017-05-15 香豆素荧光探针的制备方法及其应用 Active CN107021953B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710338890.0A CN107021953B (zh) 2017-05-15 2017-05-15 香豆素荧光探针的制备方法及其应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710338890.0A CN107021953B (zh) 2017-05-15 2017-05-15 香豆素荧光探针的制备方法及其应用

Publications (2)

Publication Number Publication Date
CN107021953A true CN107021953A (zh) 2017-08-08
CN107021953B CN107021953B (zh) 2019-11-08

Family

ID=59529657

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710338890.0A Active CN107021953B (zh) 2017-05-15 2017-05-15 香豆素荧光探针的制备方法及其应用

Country Status (1)

Country Link
CN (1) CN107021953B (zh)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108219774A (zh) * 2017-10-19 2018-06-29 泰山医学院 一种吡啶并[1,2-a]苯并咪唑取代的喹啉类检测次氯酸的荧光探针及其应用
CN108398409A (zh) * 2018-02-06 2018-08-14 河南牧业经济学院 一种荧光比率检测次氯酸根的方法
CN108689925A (zh) * 2018-05-16 2018-10-23 延边大学 基于1,8-二氨基萘单元的次氯酸和一氧化氮荧光探针
CN109796966A (zh) * 2019-02-25 2019-05-24 山东大学 一种次氯酸比率荧光探针及其应用
CN110041305A (zh) * 2019-05-15 2019-07-23 三峡大学 吲哚半菁荧光探针，制备方法及在氰根离子检测上的应用
CN110373181A (zh) * 2019-07-09 2019-10-25 济南大学 一种检测氟离子的荧光探针
CN111116564A (zh) * 2019-12-11 2020-05-08 江苏大学 检测次氯酸根离子的比率型荧光分子探针及其制备方法和应用
CN113004238A (zh) * 2021-03-19 2021-06-22 温州医科大学 一种多功能小分子荧光探针、制备方法及应用
CN113218922A (zh) * 2021-03-12 2021-08-06 天津理工大学 一种基于香豆素骨架快速检测次氯酸根比率型荧光探针及应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105647220A (zh) * 2016-01-20 2016-06-08 三峡大学 一种D-π-A结构硼氟染料及制备方法和应用
CN105669644A (zh) * 2016-02-03 2016-06-15 三峡大学 一种苯并咪唑喹啉衍生物，制备方法及其应用
CN106987152A (zh) * 2017-03-08 2017-07-28 三峡大学 一类氟硼近红外荧光染料及在非质子性溶剂中微量水的检测上的应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105647220A (zh) * 2016-01-20 2016-06-08 三峡大学 一种D-π-A结构硼氟染料及制备方法和应用
CN105669644A (zh) * 2016-02-03 2016-06-15 三峡大学 一种苯并咪唑喹啉衍生物，制备方法及其应用
CN106987152A (zh) * 2017-03-08 2017-07-28 三峡大学 一类氟硼近红外荧光染料及在非质子性溶剂中微量水的检测上的应用

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DAN CHENG，等: "Selective Visualization of the Endogenous Peroxynitrite in an Inflamed Mouse Model by a Mitochondria-Targetable Two-Photon Ratiometric Fluorescent Probe", 《J. AM. CHEM. SOC.》 *
JIAYU ZHA，等: "A ratiometric fluorescent probe for rapid and sensitive visualization of hypochlorite in living cells", 《RSC ADV》 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108219774A (zh) * 2017-10-19 2018-06-29 泰山医学院 一种吡啶并[1,2-a]苯并咪唑取代的喹啉类检测次氯酸的荧光探针及其应用
CN108398409B (zh) * 2018-02-06 2020-10-27 河南牧业经济学院 一种荧光比率检测次氯酸根的方法
CN108398409A (zh) * 2018-02-06 2018-08-14 河南牧业经济学院 一种荧光比率检测次氯酸根的方法
CN108689925A (zh) * 2018-05-16 2018-10-23 延边大学 基于1,8-二氨基萘单元的次氯酸和一氧化氮荧光探针
CN108689925B (zh) * 2018-05-16 2021-03-16 延边大学 基于1,8-二氨基萘单元的次氯酸和一氧化氮荧光探针
CN109796966A (zh) * 2019-02-25 2019-05-24 山东大学 一种次氯酸比率荧光探针及其应用
CN109796966B (zh) * 2019-02-25 2021-11-12 山东大学 一种次氯酸比率荧光探针及其应用
CN110041305A (zh) * 2019-05-15 2019-07-23 三峡大学 吲哚半菁荧光探针，制备方法及在氰根离子检测上的应用
CN110041305B (zh) * 2019-05-15 2021-05-18 三峡大学 吲哚半菁荧光探针，制备方法及在氰根离子检测上的应用
CN110373181B (zh) * 2019-07-09 2021-05-04 济南大学 一种检测氟离子的荧光探针
CN110373181A (zh) * 2019-07-09 2019-10-25 济南大学 一种检测氟离子的荧光探针
CN111116564A (zh) * 2019-12-11 2020-05-08 江苏大学 检测次氯酸根离子的比率型荧光分子探针及其制备方法和应用
CN111116564B (zh) * 2019-12-11 2022-04-26 江苏大学 检测次氯酸根离子的比率型荧光分子探针及其制备方法和应用
CN113218922A (zh) * 2021-03-12 2021-08-06 天津理工大学 一种基于香豆素骨架快速检测次氯酸根比率型荧光探针及应用
CN113004238A (zh) * 2021-03-19 2021-06-22 温州医科大学 一种多功能小分子荧光探针、制备方法及应用
CN113004238B (zh) * 2021-03-19 2022-05-06 温州医科大学 一种多功能小分子荧光探针、制备方法及应用

Also Published As

Publication number Publication date
CN107021953B (zh) 2019-11-08

Similar Documents

Publication Publication Date Title
CN107021953B (zh) 香豆素荧光探针的制备方法及其应用
Yang et al. A NIR ratiometric probe for hydrazine “naked eye” detection and its imaging in living cell
Ye et al. A novel colorimetric and ratiometric fluorescent probe for visualizing SO2 derivatives in environment and living cells
Wang et al. Rapidly responsive and highly selective fluorescent probe for bisulfite detection in food
Yang et al. A ratiometric colorimetric and fluorescent chemosensor for rapid detection hydrogen sulfide and its bioimaging
CN108003869B (zh) 一种高灵敏检测次氯酸根的荧光探针及其合成方法与应用
Zhu et al. A highly specific and ultrasensitive fluorescent probe for monitoring hypochlorous acid and its applications in live cells
Peng et al. A novel fluorescent probe for selective detection of hydrogen sulfide in living cells
Lan et al. All-in-one: Accurate quantification, on-site detection, and bioimaging of sulfite using a colorimetric and ratiometric fluorescent probe in vitro and in vivo
Lin et al. A two-photon near-infrared fluorescent probe for imaging endogenous hypochlorite in cells, tissue and living mouse
Zhao et al. A new “off-on” NIR fluorescence probe for determination and bio-imaging of mitochondrial hypochlorite in living cells and zebrafish
CN111073636B (zh) 一种用于甲醛检测的荧光探针及其制备方法与应用
CN110015992A (zh) 一种用于二氧化硫/亚硫酸(氢)盐检测的荧光探针及其制备方法和应用
CN106810561A (zh) 一种溶酶体靶向次氯酸比率荧光探针及其制备方法与应用
CN113121513A (zh) 一种咔唑-香豆素基腙类化合物及其制备方法和用途
CN107141256A (zh) 一种快速高选择性超灵敏硫化氢比率荧光探针及其制备方法
CN110128418A (zh) 一种基于半花菁结构衍生物的近红外荧光探针及其制备方法和应用
CN103387830B (zh) 一种铬离子比率型荧光探针及其制备方法和应用
Li et al. Development of a responsive probe for colorimetric and fluorescent detection of bisulfite in food and animal serum samples in 100% aqueous solution
Zhang et al. A colorimetric and far-red fluorescent probe for rapid detection of bisulfite/sulfite in full water-soluble based on biquinolinium and its applications
Dong et al. Selective visualization of cyanide in food, living cells and zebrafish by a mitochondria targeted NIR-emitting fluorescent probe
Yu et al. Enhancing probe’s sensitivity for peroxynitrite through alkoxy modification of dicyanovinylchromene
CN112945925B (zh) 一种香豆素基探针检测高锰酸根的方法
CN110452250A (zh) 一种荧光素母体结构的检测肼用荧光探针
CN107365289B (zh) 一种次氯酸响应型荧光传感材料的制备方法与应用

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
GR01 Patent grant
GR01 Patent grant