CN110317175A - 一种萘衍生物及其合成方法和应用 - Google Patents
一种萘衍生物及其合成方法和应用 Download PDFInfo
- Publication number
- CN110317175A CN110317175A CN201910558697.7A CN201910558697A CN110317175A CN 110317175 A CN110317175 A CN 110317175A CN 201910558697 A CN201910558697 A CN 201910558697A CN 110317175 A CN110317175 A CN 110317175A
- Authority
- CN
- China
- Prior art keywords
- naphthalene derivatives
- concentration
- synthetic method
- fluorescence intensity
- solution
- 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
Links
- 150000002790 naphthalenes Chemical class 0.000 title claims abstract description 38
- 238000010189 synthetic method Methods 0.000 title claims abstract description 11
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 claims abstract description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000001514 detection method Methods 0.000 claims abstract description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000019441 ethanol Nutrition 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims abstract description 6
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 5
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011550 stock solution Substances 0.000 claims description 9
- 238000005259 measurement Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007995 HEPES buffer Substances 0.000 claims description 2
- 238000013507 mapping Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 239000007853 buffer solution Substances 0.000 claims 1
- 238000007811 spectroscopic assay Methods 0.000 claims 1
- 239000000523 sample Substances 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 150000001768 cations Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000003139 buffering effect Effects 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910003307 Ni-Cd Inorganic materials 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 210000002659 acromion Anatomy 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- OJIJEKBXJYRIBZ-UHFFFAOYSA-N cadmium nickel Chemical compound [Ni].[Cd] OJIJEKBXJYRIBZ-UHFFFAOYSA-N 0.000 description 1
- 208000022458 calcium metabolism disease Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003891 environmental analysis Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- -1 metals ion Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000002686 phosphate fertilizer Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- 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
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
Abstract
本发明提供了一种萘衍生物及其合成方法和应用，属于萘衍生物和镉离子的检测领域。萘衍生物的合成方法：将2，3‑二氨基萘和咪唑‑2‑甲醛在甲醇和乙醇的混合溶液(v/v＝1：1)中加热回流，抽滤，洗涤得到。本发明还提供了一种检测镉离子的方法：以萘衍生物为探针，在EtOH‑H2O(pH＝7.4)的溶液中定量检测Cd2+的含量。该检测方法可以高选择性、高灵敏性地检测水溶液中的镉离子，操作简单、方便、快捷。
Description
技术领域
本发明涉及镉离子检测试剂，具体涉及一种萘衍生物及其合成方法和在检测Cd2+中的应用。
背景技术
镉是一种剧毒的重金属，即使在低浓度下也会引起严重的健康问题。通过直接摄入受污染的水或食物或通过香烟烟雾暴露摄入Cd2+会对人体肾脏，肺脏，骨骼和神经系统产生毒性作用，导致肾功能不全，钙代谢紊乱和各种癌症发病率增加。但是，镉作为一种重要的天然元素已被广泛应用于采矿，冶金，军事，农业中含Cd的磷肥的应用，镍镉充电电池的生产等。所有这些应用都大大提高了环境污染的可能性，并可能导致镉暴露水平增加。由于其不可生物降解的性质和在人体中长的消除半衰期(10-30年)，镉被美国环境保护署(EPA)列为126种污染物之一。由世界卫生组织(WHO)和美国环境保护署(EPA)设定的饮用水中Cd2+的最大允许浓度分别为3μgL-1和5μgL-1。因此，在环境分析和生命科学领域非常需要高选择性和高灵敏度的荧光探针用于Cd2+的检测。
荧光光谱法具有灵敏度高，准确度较高，操作简便快速的特点，并且通常伴随着溶液颜色的变化，可以通过裸眼识别进行快速检测分析。比率荧光传感更有利，因为测量两个不同波长的发射强度比可以减少外部因素的影响，从而大大提高测量的可靠性。
发明内容
本发明的目的在于提供一种萘衍生物及其合成方法和在检测Cd2+中的应用。该萘衍生物能避免多种金属离子的干扰，可以通过光谱法高选择性、高灵敏性地检测水溶液中的镉离子，操作简单、方便、快捷，不需要特殊仪器设备和专业培训，易于推广，结果清晰易辩。
为实现上述目的，本发明提供的技术方案为：
一种萘衍生物，其结构式为：
一种萘衍生物的合成方法，包括如下步骤：将反应物2，3-二氨基萘和咪唑-2-甲醛在甲醇和乙醇的混合溶液(v/v＝1:1)加热回流，反应20-25小时，抽滤，洗涤得到萘衍生物NIS。
反应式如下：
作为优选，所述步骤中2，3-二氨基萘和咪唑-2-甲醛的摩尔比为1:2-2.2。
为了保证反应物能充分反应，得到纯净的产物，优选反应时间为24小时。
为了保证反应物能充分反应，得到纯净的产物，优选加热回流温度为80℃。
一种比率荧光光谱法用于检测镉离子的方法，包括如下步骤：
(1)配置10-3M萘衍生物的DMSO储备液，配置10-2M Cd2+的水溶液；
(2)取20μL萘衍生物储备液加入干净的比色管中，随着Cd2+浓度的增加，在荧光光度计上测定472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强，体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系(R2＝0.98306)，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F＝3658.41667+131.40774[Cd2+]；
(3)取2.5mL含有4×10-6M萘衍生物的EtOH-水溶液加入干净的比色管中，取xμL待测样品溶液加入，在荧光分光光度计上检测，测得的荧光强度，带入步骤(2)的线性方程，得到[Cd2+]的浓度，待测样品[Cd2+]待测＝5000μL×[Cd2+]×10-6/xμL,即可求得Cd2+的浓度。
与现有技术相比，本发明具有以下优点和效果：
(1)方法经济：萘衍生物制备所需试剂价格便宜，产物收率高，检测成本低。
(2)特异性高：萘衍生物在水溶液中可高选择性地实现对镉离子的检测，不受其他共存阳离子的干扰，尤其不受具有相似结构Zn2+的影响。
(3)快捷：检测时间只需30-60s，完全能够满足紧急情况的检测需要。
(4)操作简单方便：只需通过荧光分光光度计进行检测，检测手段简便，结果清晰可辩。
附图说明
图1为本发明萘衍生物用于测定Cd2+的荧光光谱图；
图2为本发明萘衍生物测定Cd2+的工作曲线图；
图3为本发明萘衍生物用于测定Cd2+的紫外吸收光谱图；
图4为本发明实施例4共存金属离子对NIS-Cd2+体系的影响对比图。
具体实施方式
实施例1 2，3-二氨基萘衍生物的合成和表征
在50mL圆底烧瓶中，将2,3-二氨基萘(0.079g，0.5mmol)和咪唑-2-甲醛(0.1g，1.1mmol)溶解在混合的乙醇-甲醇溶剂中(20mL，v/v＝1：1)，然后加入2-3滴乙酸。将所得混合物加热回流(80℃)，将其连续搅拌24小时，然后冷却至室温。过滤出固体，用CH3OH洗涤并在真空下干燥，得到黄色固体，即为本技术所述萘衍生物。1H NMR(600MHz,DMSO-d6),δ(ppm):8.423(1H,s),8.199(1H,s),8.0045(2H,d),7.943(1H,s),7.915(1H,m),7.626(1H,s),7.467(1H,m),7.413(1H,s),7.378(2H,t),7.241(1H,s),13.468(1H,s),13.085(1H,s).13C NMR(DMSO-d6):δ148.669,144.566,138.750,135.711,130.813,130.416,130.251,128.411,127.884,124.279,123.555,120.482,115.304,107.351.HRMS(ESI):calcd.forC18H14N6(M+H)+315.13584,found 315.13480.
实施例2 2，3-二氨基萘衍生物用于Cd2+的荧光光谱测定
用DMSO配置1mM的萘衍生物储备液，用蒸馏水配置0.01M的Cd2+溶液，并配置pH＝7.4、浓度为0.025M的HEPES缓冲溶液；取20μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、12μL、14μL)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测，随着Cd2+的加入，472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强。荧光光谱图见图1。
实施例3萘衍生物测定Cd2+的线性关系
取20μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、12μL、14μL)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测，随着Cd2+的加入，472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强。体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系(R2＝0.98306)，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F＝3658.41667+131.40774[Cd2+]，[Cd2+]的单位为10-6mol/L；工作线性图见图2。
实施例4萘衍生物用于Cd2+的紫外吸收测定
取100μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、15μL、20μL、25μL、30μL、40μL、50μL、60μL、70μL)，加入0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在紫外可见分光光度计上检测，随着Cd2+的加入，在272nm处的吸收峰逐渐减弱，283nm处的吸收峰逐渐减弱，并且342nm处的吸收峰发生红移至347nm，365nm处出现肩峰。紫外光谱吸收图见图3。
实施例5共存阳离子对Cd2+的干扰性的荧光测定
取20μL的萘衍生物储备液加入干净的比色管中，分别加入20μL的Cd2+，14μL的其他各种阳离子(K+,Ca2+,Na+,Mg2+,Al3+,Zn2+,Hg2+,Ag+,Pb2+,Co2+,Ni2+,Cr3+,Hg2+,Fe3+)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测。共存阳离子对NIS-Cd2+的荧光强度的干扰见图4。
实验证明，其它常见阳离子不干扰体系对Cd2+的测定。
Claims (7)
1.一种萘衍生物，其特征在于，结构式为：
2.如权利要求1所述的萘衍生物的合成方法，其特征在于，包括如下步骤：将反应物2，3-二氨基萘和咪唑-2-甲醛在体积比1：1的甲醇和乙醇的混合溶液中加热回流，反应20-25小时，抽滤，洗涤得到萘衍生物。
3.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述2，3-二氨基萘和咪唑-2-甲醛的摩尔比为1:2-2.2。
4.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述的反应时间为24小时。
5.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述加热回流温度为80℃。
6.如权利要求1所述的萘衍生物在检测Cd2+中的应用。
7.一种比率荧光光谱测定Cd2+的方法，其特征在于，包括如下步骤：
(1)用DMSO配置1mM的如权利要求1所述的萘衍生物的储备液，用蒸馏水配置10-2M的Cd2+溶液，并配置pH＝7.4、浓度为25mM的HEPES的缓冲溶液；
(2)取20μL萘衍生物储备液加入干净的比色管中，随着Cd2+浓度的增加，在荧光光度计上测定472nm处的荧光强度逐渐减弱，398nm处的荧光强度逐渐增强，体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系(R2＝0.98306)，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F＝3658.41667+131.40774[Cd2+]；
(3)取2.5mL含有4×10-6M萘衍生物的EtOH-水溶液加入干净的比色管中，取xμL待测样品溶液加入，在荧光分光光度计上检测，测得的荧光强度，带入步骤(2)的线性方程，得到[Cd2+]的浓度，待测样品[Cd2+]待测＝5000μL×[Cd2+]×10-6/xμL，即可求得Cd2+的浓度。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910558697.7A CN110317175B (zh) | 2019-06-26 | 2019-06-26 | 一种萘衍生物及其合成方法和应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910558697.7A CN110317175B (zh) | 2019-06-26 | 2019-06-26 | 一种萘衍生物及其合成方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110317175A true CN110317175A (zh) | 2019-10-11 |
| CN110317175B CN110317175B (zh) | 2021-11-19 |
Family
ID=68120292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910558697.7A Active CN110317175B (zh) | 2019-06-26 | 2019-06-26 | 一种萘衍生物及其合成方法和应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110317175B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112250674A (zh) * | 2020-10-27 | 2021-01-22 | 山西大学 | 一种2，3-二氨基吩嗪衍生物及其合成方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104498023A (zh) * | 2014-11-26 | 2015-04-08 | 南京大学 | 一种新型的含喹啉的荧光比率探针在检测Cd2+中的应用 |
| CN108727257A (zh) * | 2018-08-07 | 2018-11-02 | 陕西科技大学 | 一种用于检测镉离子的荧光化学传感器及制备方法 |
| CN109503565A (zh) * | 2018-12-29 | 2019-03-22 | 河南坤和信息科技有限公司 | 一种镉离子检测试剂及其制备方法和应用 |
-
2019
- 2019-06-26 CN CN201910558697.7A patent/CN110317175B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104498023A (zh) * | 2014-11-26 | 2015-04-08 | 南京大学 | 一种新型的含喹啉的荧光比率探针在检测Cd2+中的应用 |
| CN108727257A (zh) * | 2018-08-07 | 2018-11-02 | 陕西科技大学 | 一种用于检测镉离子的荧光化学传感器及制备方法 |
| CN109503565A (zh) * | 2018-12-29 | 2019-03-22 | 河南坤和信息科技有限公司 | 一种镉离子检测试剂及其制备方法和应用 |
Non-Patent Citations (2)
| Title |
|---|
| KARUPPIAH KRISHNAVENI，等: "A new multifunctional benzimidazole tagged coumarin as ratiometric fluorophore for the detection of Cd2+/F− ions and imaging in live cells", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| 王宇斌，等: "检测Al3+ 的席夫碱荧光探针的合成和性能研究", 《分析化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112250674A (zh) * | 2020-10-27 | 2021-01-22 | 山西大学 | 一种2，3-二氨基吩嗪衍生物及其合成方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110317175B (zh) | 2021-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100360932C (zh) | 一类检测水中汞离子的化学试剂及其制备方法 | |
| Chen et al. | A new off–on chemosensor for Al 3+ and Cu 2+ in two different systems based on a rhodamine B derivative | |
| CN110229147A (zh) | 一种香豆素-苯并噻唑基腙类化合物及其制备方法和用途 | |
| CN107286102A (zh) | 一种小分子聚集态荧光增强型汞离子探针 | |
| CN109142306A (zh) | 一种裸眼或荧光检测Ag+双菲并咪唑探针及使用方法 | |
| CN103666451A (zh) | 一种用于Fe3+、Cr3+检测与识别的含有咔唑-噻吩基席夫碱荧光探针化合物 | |
| Mattison et al. | Small molecule optical sensors for nickel: The quest for a universal nickel receptor | |
| CN107746406B (zh) | 一种超灵敏高选择性次氯酸荧光探针的制备及应用 | |
| Chen et al. | A fluorescent and colorimetric probe based on isatin-appended rhodamine for the detection of Hg2+ | |
| CN106518763B (zh) | 一种选择性比率式检测氰根离子的荧光探针及其合成方法与应用 | |
| CN102516978A (zh) | 用于检测水中汞离子及银离子的分子探针及其制备方法 | |
| Hu et al. | A rhodamine-based dual chemosensor for the naked-eye detection of Hg 2+ and enhancement of the fluorescence emission for Fe 3+ | |
| CN104132920A (zh) | 一种荧光猝灭测定Ag+或F-的方法 | |
| CN104789209A (zh) | 一种基于罗丹明B的水溶性Cu2+、Hg2+探针及其制备方法和应用 | |
| CN113004256B (zh) | 一种检测汞离子的比率型探针及其制备方法和应用 | |
| CN113087651B (zh) | 一种含有吲哚基团的化合物及其制备方法和应用 | |
| CN105131004B (zh) | 1‑萘基异硫氰酸酯修饰的罗丹明b衍生物、制备方法以及应用 | |
| CN110317175A (zh) | 一种萘衍生物及其合成方法和应用 | |
| CN108640867A (zh) | 一种含有氰基-咔唑基席夫碱荧光探针化合物及其制备方法和用途 | |
| CN104892504B (zh) | 一种能连续识别CN‑和Cu2+的传感器分子及其合成和应用 | |
| CN107501284B (zh) | 一种探针及应用该探针同时检测微量Cu2+和/或Hg2+的方法 | |
| CN110627737A (zh) | 一种检测锌离子的水溶性苯并恶唑类荧光探针及制备方法和应用 | |
| CN107831165B (zh) | 一种双通道铜离子检测试纸及其制备方法 | |
| CN107402206B (zh) | 一种汞离子比色传感器及其制备方法和应用 | |
| CN109776519A (zh) | 一种7-硝基-1,2,3-苯并恶二唑衍生物及其合成方法和应用 |
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 |