CN113698353A - 一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 - Google Patents
一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 Download PDFInfo
- Publication number
- CN113698353A CN113698353A CN202110999929.XA CN202110999929A CN113698353A CN 113698353 A CN113698353 A CN 113698353A CN 202110999929 A CN202110999929 A CN 202110999929A CN 113698353 A CN113698353 A CN 113698353A
- Authority
- CN
- China
- Prior art keywords
- imidazolyl
- schiff base
- compound
- particles
- fluorescence sensor
- 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
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000002245 particle Substances 0.000 title claims abstract description 22
- -1 Imidazolyl Schiff base Chemical class 0.000 title claims abstract description 16
- 239000002262 Schiff base Substances 0.000 title claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 9
- 238000010189 synthetic method Methods 0.000 title description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims abstract description 5
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 229940125782 compound 2 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- IRGONGJBIVBVLQ-UHFFFAOYSA-N N=1C2=CC(N)=CC=C2NC=1C1=CC=CC=C1O Chemical compound N=1C2=CC(N)=CC=C2NC=1C1=CC=CC=C1O IRGONGJBIVBVLQ-UHFFFAOYSA-N 0.000 claims description 4
- NLOABUHTENDFSD-UHFFFAOYSA-N chembl1944806 Chemical compound OC1=CC=CC=C1C1=NC2=CC([N+]([O-])=O)=CC=C2N1 NLOABUHTENDFSD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007853 buffer solution Substances 0.000 description 4
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
-
- 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
- C09K2211/1007—Non-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (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 Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110999929.XA CN113698353B (zh) | 2021-08-27 | 2021-08-27 | 一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110999929.XA CN113698353B (zh) | 2021-08-27 | 2021-08-27 | 一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113698353A true CN113698353A (zh) | 2021-11-26 |
CN113698353B CN113698353B (zh) | 2023-05-05 |
Family
ID=78656388
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110999929.XA Active CN113698353B (zh) | 2021-08-27 | 2021-08-27 | 一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113698353B (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103320118A (zh) * | 2013-05-08 | 2013-09-25 | 济南大学 | 一种希夫碱铜离子荧光探针及其制备方法 |
CN108586382A (zh) * | 2018-04-08 | 2018-09-28 | 山西大学 | 一种希夫碱化合物及其制备和在铜离子检测中的应用 |
KR20190025788A (ko) * | 2017-09-01 | 2019-03-12 | 삼성디스플레이 주식회사 | 벤즈아졸 유도체를 리간드로 하는 유기 금속 착물 및 이를 포함한 유기 전계발광 소자 |
CN112812075A (zh) * | 2020-12-30 | 2021-05-18 | 山西大学 | 一种基于苯并噻唑类希夫碱荧光探针的制备方法及应用 |
-
2021
- 2021-08-27 CN CN202110999929.XA patent/CN113698353B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103320118A (zh) * | 2013-05-08 | 2013-09-25 | 济南大学 | 一种希夫碱铜离子荧光探针及其制备方法 |
KR20190025788A (ko) * | 2017-09-01 | 2019-03-12 | 삼성디스플레이 주식회사 | 벤즈아졸 유도체를 리간드로 하는 유기 금속 착물 및 이를 포함한 유기 전계발광 소자 |
CN108586382A (zh) * | 2018-04-08 | 2018-09-28 | 山西大学 | 一种希夫碱化合物及其制备和在铜离子检测中的应用 |
CN112812075A (zh) * | 2020-12-30 | 2021-05-18 | 山西大学 | 一种基于苯并噻唑类希夫碱荧光探针的制备方法及应用 |
Non-Patent Citations (2)
Title |
---|
MASAHIRO MUTO ET AL.: "Tripodal Trimanganese(III) Complexes of New Unsymmetrical Pentadentate Ligands Derived from 2-(Salicylideneamino)phenol: Syntheses, Crystal Structures and Properties" * |
RAJASEKHAR YERRASANI ET AL.: "Thermal, optical and Photophysical behaviour of some Mesogenic Benzimidazole-based Schiff-bases" * |
Also Published As
Publication number | Publication date |
---|---|
CN113698353B (zh) | 2023-05-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113979998B (zh) | 基于1,8-萘酰亚胺为母体的铝离子检测荧光探针及其制备方法和应用 | |
CN104962278B (zh) | 一种钯离子荧光探针及其制备方法和应用 | |
CN106632064B (zh) | 可逆双羟基菲并咪唑Hg2+荧光探针合成与使用方法 | |
CN109232626B (zh) | 一种基于二氟硼氧基香豆素的so2比率型荧光探针 | |
CN109608414B (zh) | 检测过氧亚硝酸根的荧光探针及其制备方法和应用 | |
CN111808109B (zh) | 一种哒嗪并喹喔啉二胺席夫碱钴离子荧光探针及其制备方法 | |
CN113121576B (zh) | 一种对酸、碱环境具有不同检测信号的分子传感器及应用 | |
CN113620891B (zh) | 一种可控催化制备喹喔啉-2-酮类衍生物的方法 | |
CN109608382B (zh) | 一种检测氰根离子和次氯酸的荧光探针及其制备和应用 | |
CN101475539B (zh) | 一种制备高纯度氧嗪酸钾的精制方法 | |
CN107892654B (zh) | 一类异长叶烷基荧光型酸碱指示剂及其合成方法和应用 | |
CN108250211B (zh) | 一种用于检测Zn2+的荧光探针及其制备方法 | |
Chen et al. | A reusable cyanide sensor via activation of C–H group: trifluoromethylcarbinol-directed meta-C–H cyanomethylation of naphthalimide | |
CN113698353B (zh) | 一种用于水溶液中铜(ii)粒子检测的咪唑基希夫碱荧光传感器及其合成方法 | |
CN117105760A (zh) | 识别手性组氨酸的化合物、荧光探针及其制备方法和应用 | |
CN103044406A (zh) | 香豆素类衍生物及其制备方法和在检测氰根离子中的应用 | |
CN108623611B (zh) | 一种检测过氧化氢的荧光探针的合成与应用 | |
CN109912512B (zh) | 一种新的替米沙坦杂质化合物及其制备方法和用途 | |
CN113912612B (zh) | 一种碱性pH荧光探针哒嗪并[4,5-b]喹喔啉-1,4-二胺席夫碱及其制备方法和应用 | |
CN106220531B (zh) | 用于识别铜离子的荧光探针、膜材料、制备方法及应用 | |
CN112538051B (zh) | 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法 | |
CN110964516B (zh) | 一种吡唑类Schiff碱荧光探针、其合成方法及其应用 | |
CN110964022A (zh) | 一种检测过氧亚硝酸根离子的荧光探针及其制备方法和应用 | |
CN109535114B (zh) | 一种对NaClO敏感的荧光化合物及其制备与应用 | |
CN108949159B (zh) | 一种检测钯离子的荧光探针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 | ||
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20211126 Assignee: URIT Medical Electronic Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980044137 Denomination of invention: An imidazole based Schiff base fluorescence sensor and its synthesis method for detecting copper (II) particles in aqueous solutions Granted publication date: 20230505 License type: Common License Record date: 20231023 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20211126 Assignee: URIT Medical Electronic Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980044257 Denomination of invention: An imidazole based Schiff base fluorescence sensor and its synthesis method for detecting copper (II) particles in aqueous solutions Granted publication date: 20230505 License type: Common License Record date: 20231026 |