CN103497189A - 1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 - Google Patents
1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 Download PDFInfo
- Publication number
- CN103497189A CN103497189A CN201310470705.5A CN201310470705A CN103497189A CN 103497189 A CN103497189 A CN 103497189A CN 201310470705 A CN201310470705 A CN 201310470705A CN 103497189 A CN103497189 A CN 103497189A
- Authority
- CN
- China
- Prior art keywords
- tetracarboxylic acid
- perylene tetracarboxylic
- acid diimides
- hydroxyl
- tetracarboxylic diimide
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000011737 fluorine Substances 0.000 title claims abstract description 17
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 17
- 238000005259 measurement Methods 0.000 title claims abstract description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title abstract 6
- 229910000071 diazene Inorganic materials 0.000 title abstract 6
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 8
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 8
- -1 halogen ions Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002500 ions Chemical class 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- 238000000207 volumetry Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003759 clinical diagnosis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007860 molecular communication Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000003958 nerve gas Substances 0.000 description 1
- 238000004204 optical analysis method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001009 osteoporotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004557 single molecule detection Methods 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
- G01N21/17—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"
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
本发明涉及1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用。将1-NO2-3,4:9,10-苝四羧酸二酰亚胺与碱性盐混合溶于极性有机溶剂中40-80℃反应2-4小时，得到1-OH-3,4:9,10-苝四羧酸二酰亚胺。1-OH-3,4:9,10-苝四羧酸二酰亚胺对环境中F-的变化有着非常敏锐的吸收及荧光的变化并且不受其他卤素离子的干扰，可以用于对氟离子检测。
Description
技术领域
本发明涉及1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及应用，属于有机合成技术领域。
背景技术
氟是人体必需的微量元素之一，它以氟化物的形式广泛分布于土壤、水和动植物等整个中自然界，并且与生活饮用水、龋齿防治、骨质疏松的临床诊断及神经毒气、核武器的铀提炼等密切相关。氟是一种累积性毒物，动植物体内含氟量超过一定程度可引起氟中毒，因此氟含量的测定在环境氟污染和地方性氟中毒的监测、评价和防治控制中具有重要的意义。
目前传统的检测方法包括：容量分析法、光学分析法、比色法、离子色谱法、氟离子选择电级等。容量法是比较准确、简便快速的分析方法，但常用的钍或锆、铝盐容量分析法滴定不明显；离子色谱色法是一种分析无机和有机离子的液相色谱技术，非常适合于多组分与多元素的同时分析，其灵敏度高、选择性好，样品用量少，易实现自动化，但该设备价格较高，难以普及；氟离子选择电极法已成为测定氟离子浓度的经典标准方法，氟离子选择电极具有良好的性能，很好的选择性，主要应用于水及无机溶液中氟化物的测定、矿物材料中氟的测定、有机或生物原料中氟含量的测定以及大气中氟气体的测定等多种领域。
分子吸收、荧光作为传感信号可达到单分子检测的高灵敏性、可开关、可实现人与分子的通讯、对亚微粒具有可视的亚纳米空间分辨并且是亚毫秒时间分辨的，广泛应用于生物化学、细胞生物学和分析化学等相关领域。因此设计合成简便易用、反应迅速、准确灵敏等特性的氟离子荧光化学传感器一直受到人们的重视。
苝二酰亚胺具有大的共轭π体系，是封闭的缺电子发色体系，有着强烈荧光的芳香类化合物，同时具有优异的化学、热和光化学稳定性，对可见区到红外区的光有很强的吸收，荧光量子产率几乎是定量，且产率和寿命不受氧的影响。因此，苝二酰亚胺可以作为一种优良的荧光探针分子的信号单元，经过化学修饰，利用其优异的光学特性，可对特定物质进行选择性检测。
发明内容
本发明的目的是克服上述不足而提供一种1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用。
本发明采取的技术方案为：
1-羟基-3,4:9,10-苝四羧酸二酰亚胺，其结构式如下：
其中，R1为任意烃基，优选脂肪烃基，进一步优选C1-8的直链、支链烷烃或环烷烃。
所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，包括步骤如下：
将1-NO2-3,4:9,10-苝四羧酸二酰亚胺与碱性盐混合溶于极性有机溶剂中，所述的1-NO2-3,4:9,10-苝四羧酸二酰亚胺与碱性盐的质量比为5-7:2-4，极性有机溶剂的用量为每克1-NO2-3,4:9,10-苝四羧酸二酰亚胺用40-50毫升；加热，40-80℃反应2-4小时，得到1-OH-3,4:9,10-苝四羧酸二酰亚胺。
所述的碱性盐为羧酸盐、碳酸盐或碳酸氢盐，优选乙酸钠。
所述的极性有机溶剂为N-甲基吡咯烷酮、N,N’-二甲基甲酰胺或N,N’-二甲基乙酰胺，优选N-甲基吡咯烷酮。
本发明合成路线：
注：M为金属离子
R1、R2为任意烃基。
所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺在氟含量测定中的应用。应用方法为：将样品的溶液加入到1-羟基-3,4:9,10-苝四羧酸二酰亚胺的溶液中，利用紫外可见分光光度法测700-800nm吸收强度，对比工作曲线求得样品中的氟含量。
本发明的有益效果是：
（1）该化合物为未见报道的新化合物，一步反应完成、反应时间短、反应条件温和、产率高。（2）1-OH-3,4:9,10-苝四羧酸二酰亚胺对环境中F-的变化有着非常敏锐的吸收及荧光的变化并且不受其他卤素离子的干扰，可以实现其对氟离子检测。
附图说明
图1本发明实施例1化合物的核磁共振氢谱；
图2本发明实施例1化合物的质谱；
图3本发明化合物在不同卤素离子环境中的紫外可见吸收光谱；
图4为1×10-5mol/L本发明化合物的二氯甲烷溶液，分别加入四丁基氟化铵、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵，使卤素离子浓度为2×10-5mol/L时的照片；
图5为1×10-5mol/L本发明化合物的二氯甲烷溶液，分别加入四丁基氟化铵、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵，使卤素离子浓度为2×10-5mol/L，在365nm紫外灯下的照片。
具体实施方式
下面结合实施例进一步说明。
实施例1
取600毫克N,N’-二环己基-1-NO2-3,4:9,10-苝四羧酸二酰亚胺和200毫克乙酸钠溶于30毫升N-甲基吡咯烷酮，加热至45℃，反应3小时，冷却，将反应液滴入到2mol/L的稀盐酸中，析出沉淀，抽滤，水洗3次，烘干。粗产品进行硅胶柱层析，淋洗液为二氯甲烷：乙酸乙酯=20:1。得到N,N’-二环己基-1-OH-3,4:9,10-苝四羧酸二酰亚胺400毫克，产率70％。
实施例2
取755毫克N,N’-二(1,5-二异丙基)苯基-1-NO2-3,4:9,10-苝四羧酸二酰亚胺和400毫克碳酸钾溶于30毫升N,N’-二甲基甲酰胺，加热至45℃，反应3.5小时，冷却，将反应液滴入到2mol/L的稀盐酸中，析出沉淀，抽滤，水洗3次，烘干。粗产品进行硅胶柱层析，淋洗液为二氯甲烷：乙酸乙酯=20:1。得到N,N’-二(1,5-二异丙基)苯基-1-OH-3,4:9,10-苝四羧酸二酰亚胺477毫克，产率66％。
实施例3
取599毫克N,N’-二环己基-1-NO2-3,4:9,10-苝四羧酸二酰亚胺和300毫克碳酸氢钾溶于30毫升N,N’-二甲基乙酰胺，加热至60℃，反应2.5小时，冷却，将反应液滴入到2mol/L的稀盐酸中，析出沉淀，抽滤，水洗3次，烘干。粗产品进行硅胶柱层析，淋洗液为二氯甲烷：乙酸乙酯=20:1。得到N,N’-二环己基-1-OH-3,4:9,10-苝四羧酸二酰亚胺389毫克，产率68％。
氟含量测定：
将产物配成1×10-5mol/L的二氯甲烷溶液，分别加入四丁基氟化铵、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵，使卤素离子浓度为2×10-5mol/L。对产物空白样及添加卤素离子的试样进行紫外可见吸收光谱、荧光光谱测试。
Claims (8)
1.1-羟基-3,4:9,10-苝四羧酸二酰亚胺，其结构式如下：
其中，R1为任意烃基。
2.根据权利要求1所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺，其特征是，所述的R1选
脂肪烃基。
3.权利要求1所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，其特征是，包括步骤如下：将1-NO2-3,4:9,10-苝四羧酸二酰亚胺与碱性盐混合溶于极性有机溶剂中，所述的1-NO2-3,4:9,10-苝四羧酸二酰亚胺与碱性盐的质量比为5-7:2-4，极性有机溶剂的用量为每克1-NO2-3,4:9,10-苝四羧酸二酰亚胺用40-50毫升；加热，40-80℃反应2-4小时，得到1-OH-3,4:9,10-苝四羧酸二酰亚胺。
4.根据权利要求3所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，其特征是，所述的碱性盐为羧酸盐、碳酸盐或碳酸氢盐。
5.根据权利要求4所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，其特征是，所述的碱性盐为乙酸钠。
6.根据权利要求3所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，其特征是，所述的极性有机溶剂为N-甲基吡咯烷酮、N,N’-二甲基甲酰胺或N,N’-二甲基乙酰胺。
7.根据权利要求6所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺的制备方法，其特征是，所述的极性有机溶剂为N-甲基吡咯烷酮。
8.权利要求1所述的1-羟基-3,4:9,10-苝四羧酸二酰亚胺在氟含量测定中的应用。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310470705.5A CN103497189B (zh) | 2013-10-10 | 2013-10-10 | 1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310470705.5A CN103497189B (zh) | 2013-10-10 | 2013-10-10 | 1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103497189A true CN103497189A (zh) | 2014-01-08 |
| CN103497189B CN103497189B (zh) | 2015-03-25 |
Family
ID=49862473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310470705.5A Expired - Fee Related CN103497189B (zh) | 2013-10-10 | 2013-10-10 | 1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103497189B (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104101577A (zh) * | 2014-08-05 | 2014-10-15 | 贵州大学 | 一种比率吸收光度法测定Ag+或F-的方法 |
| CN105541839A (zh) * | 2016-02-05 | 2016-05-04 | 山东师范大学 | 单硝基单酰胺化3，4，9，10-苝四羧酸二酰亚胺及其制备方法 |
| CN106350060A (zh) * | 2015-07-17 | 2017-01-25 | 济南大学 | 一种反应型pH值分子探针及制备方法和用途 |
| CN107850538A (zh) * | 2015-07-09 | 2018-03-27 | 犹他大学研究基金会 | 传感器化合物和相关联的方法与设备 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101153848A (zh) * | 2007-10-10 | 2008-04-02 | 吉林大学 | 荧光离子探针及其在离子检测方面的应用 |
| DE102006048638A1 (de) * | 2006-10-13 | 2008-04-17 | Langhals, Heinz, Prof. Dr. | Perylenfarbstoffe mit NIR-Absorption, starker Fluoreszenz und großem Stokes-Shift |
-
2013
- 2013-10-10 CN CN201310470705.5A patent/CN103497189B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006048638A1 (de) * | 2006-10-13 | 2008-04-17 | Langhals, Heinz, Prof. Dr. | Perylenfarbstoffe mit NIR-Absorption, starker Fluoreszenz und großem Stokes-Shift |
| CN101153848A (zh) * | 2007-10-10 | 2008-04-02 | 吉林大学 | 荧光离子探针及其在离子检测方面的应用 |
Non-Patent Citations (2)
| Title |
|---|
| YONGJUN LI，ET AL.，: "Synthesis and Self-Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties", 《CHEM. ASIAN J.》 * |
| 滕明爽 等: "萘酰亚胺衍生物荧光探针的研究进展", 《染料与染色》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104101577A (zh) * | 2014-08-05 | 2014-10-15 | 贵州大学 | 一种比率吸收光度法测定Ag+或F-的方法 |
| CN107850538A (zh) * | 2015-07-09 | 2018-03-27 | 犹他大学研究基金会 | 传感器化合物和相关联的方法与设备 |
| US11261181B2 (en) | 2015-07-09 | 2022-03-01 | University Of Utah Research Foundation | Sensor compounds and associated methods and devices |
| US11613537B2 (en) | 2015-07-09 | 2023-03-28 | University Of Utah Research Foundation | Sensor compounds and associated methods and devices |
| CN106350060A (zh) * | 2015-07-17 | 2017-01-25 | 济南大学 | 一种反应型pH值分子探针及制备方法和用途 |
| CN106350060B (zh) * | 2015-07-17 | 2018-08-17 | 济南大学 | 一种反应型pH值分子探针及制备方法和用途 |
| CN105541839A (zh) * | 2016-02-05 | 2016-05-04 | 山东师范大学 | 单硝基单酰胺化3，4，9，10-苝四羧酸二酰亚胺及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103497189B (zh) | 2015-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Polydiacetylene-based sensor for highly sensitive and selective Pb2+ detection | |
| CN103411935B (zh) | 一种掺杂量子点比率荧光法可视化检测有机磷农药残留的方法 | |
| CN102876323B (zh) | 一种镉离子荧光探针及制备方法和用途 | |
| Jin et al. | A reversible fluorescent probe for Zn2+ and ATP in living cells and in vivo | |
| CN107188876B (zh) | 一种用于检测多硫化氢的近红外荧光探针的合成及应用 | |
| Dong et al. | A new naphthopyran-based chemodosimeter with aggregation-induced emission: Selective dual-channel detection of cyanide ion in aqueous medium and test strips | |
| CN105131935B (zh) | 快速高选择性氟离子比色探针及其制备方法 | |
| CN112939956B (zh) | 一种用于检测汞离子和次氯酸根离子的荧光探针及其制备方法和应用 | |
| CN106905310A (zh) | 一种检测次氯酸的荧光探针及其制备方法和应用 | |
| CN103497189B (zh) | 1-羟基-3,4:9,10-苝四羧酸二酰亚胺、其合成方法及在氟含量测定中的应用 | |
| CN108276383A (zh) | 一种识别碘离子的荧光探针及其制备方法和识别方法 | |
| 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 | |
| CN104003906A (zh) | 芘类荧光探针及其制备方法与应用 | |
| Zhang et al. | An “OR-AND” logic gate based multifunctional colorimetric sensor for the discrimination of Pb2+ and Cd2+ | |
| CN107417671A (zh) | 一种含喹啉取代的香豆素衍生物及其制备方法和在比率型pH荧光探针上的应用 | |
| CN105548174B (zh) | 一种光开关型测定溶液pH的探针方法 | |
| Lin et al. | A green synthesis of a simple chemosensor that could instantly detect cyanide with high selectivity in aqueous solution | |
| CN105319194B (zh) | 一种采用聚集诱导发光型荧光传感分子连续检测I‑和Hg2+的方法 | |
| Yu et al. | Enhancing probe’s sensitivity for peroxynitrite through alkoxy modification of dicyanovinylchromene | |
| CN104132920A (zh) | 一种荧光猝灭测定Ag+或F-的方法 | |
| CN104892598B (zh) | 一种1,10‑菲啰啉衍生物及其制备方法与应用 | |
| Balasubramanian et al. | A novel Schiff base derived quinoline moieties as a selective fluorophore for Sn2+ ion sensing | |
| CN108997401A (zh) | 一种用于检测铅离子的荧光探针及其制备方法 | |
| CN108774226A (zh) | 一种用于检测银离子的荧光探针及其制备方法与应用 | |
| Karakuş et al. | Fluorescein based three-channel probe for the selective and sensitive detection of CO32− ions in an aqueous environment and real water samples |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150325 Termination date: 20161010 |