CN105541697A - 一种三苯胺衍生物及其制备方法 - Google Patents
一种三苯胺衍生物及其制备方法 Download PDFInfo
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- CN105541697A CN105541697A CN201610041795.XA CN201610041795A CN105541697A CN 105541697 A CN105541697 A CN 105541697A CN 201610041795 A CN201610041795 A CN 201610041795A CN 105541697 A CN105541697 A CN 105541697A
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- triphenylamine derivative
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- 125000006617 triphenylamine group Chemical group 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000001514 detection method Methods 0.000 claims abstract description 20
- 239000000523 sample Substances 0.000 claims description 27
- 238000000862 absorption spectrum Methods 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 20
- 238000002189 fluorescence spectrum Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 10
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- 239000007850 fluorescent dye Substances 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 6
- 230000003595 spectral effect Effects 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 3
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 abstract description 7
- 150000001768 cations Chemical class 0.000 abstract description 2
- 230000035945 sensitivity Effects 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 231100000739 chronic poisoning Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- KBYOBAICCHNMNJ-UHFFFAOYSA-L diperchloryloxymercury Chemical group [Hg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O KBYOBAICCHNMNJ-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004186 food analysis Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- -1 sterilant Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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"
-
- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- 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
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pathology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Plasma & Fusion (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
Description
试样 | 1 | 2 | 3 | 4 | 5 |
理论含量 | 10-5 | 2×10-5 | 4×10-5 | 10-4 | 1.5×10-4 |
检测含量 | 0.97×10-5 | 2.02×10-5 | 3.98×10-5 | 1.02×10-4 | 1.48×10-4 |
试样 | 1 | 2 | 3 | 4 | 5 |
理论含量 | 10-5 | 2×10-5 | 4×10-5 | 10-4 | 1.5×10-4 |
检测含量 | 0.98×10-5 | 1.97×10-5 | 4.02×10-5 | 1.02×10-4 | 1.48×10-4 |
Claims (6)
Priority Applications (1)
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CN201610041795.XA CN105541697B (zh) | 2016-01-21 | 2016-01-21 | 一种三苯胺衍生物及其制备方法 |
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CN201610041795.XA CN105541697B (zh) | 2016-01-21 | 2016-01-21 | 一种三苯胺衍生物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN105541697A true CN105541697A (zh) | 2016-05-04 |
CN105541697B CN105541697B (zh) | 2018-01-12 |
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CN201610041795.XA Expired - Fee Related CN105541697B (zh) | 2016-01-21 | 2016-01-21 | 一种三苯胺衍生物及其制备方法 |
Country Status (1)
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CN (1) | CN105541697B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105717102A (zh) * | 2016-01-21 | 2016-06-29 | 北京理工大学 | 一种用三苯胺衍生物对Hg2+和CN-的高选择性识别的方法 |
CN110041266A (zh) * | 2019-06-03 | 2019-07-23 | 江苏萨瑞斯医疗科技有限公司 | 具有aie特性的三苯胺衍生物及其制备方法和应用 |
Citations (7)
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JPH05216258A (ja) * | 1992-02-03 | 1993-08-27 | Konica Corp | 電子写真感光体 |
CN102503885A (zh) * | 2011-11-28 | 2012-06-20 | 上海交通大学 | 一种新型荧光分子探针及其应用 |
CN102516994A (zh) * | 2011-12-14 | 2012-06-27 | 南京邮电大学 | 用于汞离子检测的荧光化学传感器及制备和应用方法 |
CN103992292A (zh) * | 2014-04-18 | 2014-08-20 | 西北师范大学 | 一种希夫碱类传感器分子及其合成和荧光比色检测水中cn-的应用 |
CN104710344A (zh) * | 2015-04-03 | 2015-06-17 | 齐鲁工业大学 | 一种以咔唑为中心的希夫碱类荧光探针化合物及其制备 |
CN104788356A (zh) * | 2015-04-24 | 2015-07-22 | 黑龙江大学 | 一种含吡咯基三苯胺共轭型席夫碱化合物及制备方法和应用 |
CN105181684A (zh) * | 2015-07-16 | 2015-12-23 | 西南大学 | 一种检测氰根离子的单分子层探针及其制备和应用方法 |
-
2016
- 2016-01-21 CN CN201610041795.XA patent/CN105541697B/zh not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH05216258A (ja) * | 1992-02-03 | 1993-08-27 | Konica Corp | 電子写真感光体 |
CN102503885A (zh) * | 2011-11-28 | 2012-06-20 | 上海交通大学 | 一种新型荧光分子探针及其应用 |
CN102516994A (zh) * | 2011-12-14 | 2012-06-27 | 南京邮电大学 | 用于汞离子检测的荧光化学传感器及制备和应用方法 |
CN103992292A (zh) * | 2014-04-18 | 2014-08-20 | 西北师范大学 | 一种希夫碱类传感器分子及其合成和荧光比色检测水中cn-的应用 |
CN104710344A (zh) * | 2015-04-03 | 2015-06-17 | 齐鲁工业大学 | 一种以咔唑为中心的希夫碱类荧光探针化合物及其制备 |
CN104788356A (zh) * | 2015-04-24 | 2015-07-22 | 黑龙江大学 | 一种含吡咯基三苯胺共轭型席夫碱化合物及制备方法和应用 |
CN105181684A (zh) * | 2015-07-16 | 2015-12-23 | 西南大学 | 一种检测氰根离子的单分子层探针及其制备和应用方法 |
Non-Patent Citations (6)
Title |
---|
BRIAN CONERNEY等: "The ‘Trinity’ helix: synthesis and structural characterisation of a C3-symmetric tris-bidentate ligand and its coordination to Ag(I)", 《CHEM. COMMUN.》 * |
HAILIN WEN等: "Synthesis and acidochromic, electrochromic properties of Schiff bases containing furan and triphenylamine units", 《SYNTHETIC METALS》 * |
LI WENFENG等: "A self-assembled triphenylamine-based fluorescent chemosensor for selective detection of Fe3+ and Cu2+ ions in aqueous solution", 《RSC ADV》 * |
QINGHAI SHU等: "Electrochemiluminescent polymer films with a suitable redox "turn-off" absorbance window for remote selective sensing of Hg2+", 《ANALYST》 * |
张静静: "对金属离子敏感的荧光探针的制备及其性能研究", 《齐鲁工业大学硕士学位论文》 * |
杨杨等: "三苯胺类荧光探针的研究进展", 《材料导报A:综述篇》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105717102A (zh) * | 2016-01-21 | 2016-06-29 | 北京理工大学 | 一种用三苯胺衍生物对Hg2+和CN-的高选择性识别的方法 |
CN105717102B (zh) * | 2016-01-21 | 2018-08-28 | 北京理工大学 | 一种用三苯胺衍生物对Hg2+和CN-的高选择性识别的方法 |
CN110041266A (zh) * | 2019-06-03 | 2019-07-23 | 江苏萨瑞斯医疗科技有限公司 | 具有aie特性的三苯胺衍生物及其制备方法和应用 |
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Inventor after: Shu Qinghai Inventor after: Lu Xiaoxiao Inventor after: Jin Shaohua Inventor after: Li Lijie Inventor after: Chen Shusen Inventor before: Lu Xiaoxiao Inventor before: Shu Qinghai Inventor before: Jin Shaohua Inventor before: Li Lijie Inventor before: Chen Shusen |
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