CN109265412A - 一种用于检测氟离子的探针化合物及其检测方法 - Google Patents
一种用于检测氟离子的探针化合物及其检测方法 Download PDFInfo
- Publication number
- CN109265412A CN109265412A CN201811377135.4A CN201811377135A CN109265412A CN 109265412 A CN109265412 A CN 109265412A CN 201811377135 A CN201811377135 A CN 201811377135A CN 109265412 A CN109265412 A CN 109265412A
- Authority
- CN
- China
- Prior art keywords
- fluorine ion
- probe compound
- concentration
- solution
- probe
- 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
- 239000000523 sample Substances 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title claims abstract description 25
- 238000001514 detection method Methods 0.000 title claims abstract description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000005259 measurement Methods 0.000 claims abstract description 6
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 8
- 238000002189 fluorescence spectrum Methods 0.000 claims description 6
- 230000005284 excitation Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims 1
- 239000007850 fluorescent dye Substances 0.000 abstract description 8
- -1 bisulfate ion Chemical class 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 230000002452 interceptive effect Effects 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- DVRLYACQMUSMGA-UHFFFAOYSA-M acetonitrile;tetrabutylazanium;fluoride Chemical compound [F-].CC#N.CCCC[N+](CCCC)(CCCC)CCCC DVRLYACQMUSMGA-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UQCGQRQIDBXBJZ-UHFFFAOYSA-M C(C)#N.P(=O)(O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC Chemical compound C(C)#N.P(=O)(O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC UQCGQRQIDBXBJZ-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
一种用于检测氟离子的探针化合物及其检测方法,本发明涉及一种具有氟离子检测用途的荧光探针化合物N‑3‑羟基‑4‑2’‑苯并噻唑苯‑3,5‑二苯甲氧苯甲酰胺,以及该化合物作为比率荧光探针检测氟离子的方法。本发明的氟离子荧光探针化合物检测范围较宽,响应范围2×10‑5~2×10‑3mol/L;选择性好,醋酸根、磷酸二氢根、硫酸氢根和氯离子对氟离子浓度的测定无明显干扰。适用于生物化学和环境化学等领域中氟离子的检测。
Description
技术领域
本发明属于阴离子荧光分析检测技术领域,尤其是涉及一种具有氟离子(F-)检测用途的荧光探针化合物N-3-羟基-4-2’-苯并噻唑苯-3,5-二苯甲氧苯甲酰胺,以及该化合物作为比率荧光探针检测氟离子的方法。
背景技术
阴离子广泛存在于生物体系中,在生物学、化学、医学和环境科学等领域扮演着重要的角色,因此,人们对阴离子的选择性识别和检测越来越感兴趣。在众多阴离子中,氟离子是电负性最强、离子半径最小的阴离子,广泛存在自然界之中,也是人体必需的微量元素之一,由于在龋齿预防、骨质疏松症治疗等领域的显著作用而受到特别关注。但是过量氟离子的摄入将引起氟中毒,对人体有极大的危害,导致氟斑牙,氟骨癌等疾病。因此,氟离子的识别与检测显得尤为重要。
传统的检测氟离子的方法主要有氟离子选择电极法、离子色谱法、19F NMR谱、氟试剂比色法和荧光探针法,其中,荧光探针法因具有选择性好、灵敏度高、方便快捷等特点而备受关注。目前已经报道的氟离子荧光探针多为荧光增强型探针[1-7],此类探针的量子效率易受环境影响,因此在实际应用中有一定的局限性,而比率型荧光探针可以避免检测环境的影响,实现对氟离子动态变化过程的定量检测,但是利用比率型荧光探针检测氟离子含量的报道较少[8,9],而且已报道的这类探针存在一些缺陷,如灵敏度低[8]、响应范围窄[9]等,所以发展测定氟离子的新的比率荧光探针十分重要。
[1]Cho E J,Moon J W,Ko S W,et al.Anew fluoride selective fluorescentas well as chromogenic chemosensor containing naphthalene urea derivative[J].J.Am.Chem.Soc.,2003,125(41):12376-12377.
[2]Xu G,Tarr M A.A novel fluoride sensor based on fluorescenceenhancement[J].Chem.Commun.2004,9:1050-1051.
[3]Liu X Y,Bai D R,Wang S.Charge-transfer emission in nonplanarthree-coordinate organoboron compounds for fluorescent sensing of fluoride[J].Angew.Chem.,2006,118:5601-5604.
[4]Sokkalingam P,Lee C H.Highly sensitive fluorescence“turn-on”indicator for fluoride anion with remarkable selectivity in organic andaqueous media[J].J.Org.Chem.,2011,76:3820–3828.
[5]Ke B,Chen W,Ni N,et al.A fluorescent probe for rapid aqueousfluoride detection and cell imaging[J].Chem.Commun.2013,49:2494-2496.
[6]Sui B,Kim B,Zhang Y,et al.Highly selective fluorescence turn-onsensor for fluoride detection[J].ACS Appl.Mater.Interfaces,2013,5(8):2920-2923.
[7]Sakamoto T,Hasegawa D,Fujimoto K.Fluorine-modified bisbenzimidederivative as a molecular probe for bimodal and simultaneous detection ofDNAsby19F NMR and fluorescence[J].Chem.Commun.2015,51:8749-8752.
[8]Badugu R,Lakowicz J R,Geddes C D.Awavelength-ratiometric floride-sensitive probe based on the quinolinium nucleus and boronic acid moiety[J].Sensor.Actuat.B:Chemical,2005,104(1):103-110.
[9]Yang X F,Qi H P,Wang L P,et al.Aratiometric fluorescent probe forfluoride ion employing the excited-state intramolecular proton transfer[J].Talanta,2009,80(1):92-97.
发明内容
为弥补现有技术不足,本发明提供了一种具有F-检测用途的化合物N-3-羟基-4-2’-苯并噻唑苯-3,5-二苯甲氧苯甲酰胺(简称为a)。
本发明提供的探针化合物的结构为:
本发明的探针化合物检测F-浓度的方法:
将探针化合物溶于DMSO配成浓度为1×10-3mol/L的溶液A,取溶液A溶于含有乙腈的样品池中,混合均匀后得到探针化合物浓度为1×10-5mol/L的混合液B,向混合液B中逐渐滴加含F-的乙腈溶液,使得加入后F-的摩尔浓度依次是探针化合物的2,5,10,50,80,100,150,200,230倍,分别测定每次滴加含F-的乙腈溶液后激发波长为370nm的荧光光谱,以450nm与500nm荧光强度的比值(I450/I500)为纵坐标,F-浓度与探针化合物浓度比值([F-]/[a])为横坐标做工作曲线,趋势线方程为:
I450/I500=0.0012[F-]/[a]+0.0562(R2=0.9938)。
探针化合物对F-的工作浓度范围2×10-5~2×10-3mol/L,AcO-、H2PO4 -、HSO4 -和Cl-对F-浓度的测定无明显干扰。
进一步的,所述的含F-的乙腈溶液为四丁基氟化铵的乙腈溶液。
本发明的探针化合物对F-的选择性很高,能够选择性识别F-,适用于生物化学和环境化学等领域中F-的检测。本发明的探针化合物是F-检测的比率荧光识别探针,从而消除了荧光增强型探针等受外界不稳定带来的仪器的系统误差、背景误差等,使其灵敏度提高。
附图说明
图1是本发明实施例1中探针化合物的乙腈溶液在加入不同阴离子后的荧光吸收光谱图;
图2是本发明实施例2中探针化合物的乙腈溶液在加入0-230摩尔倍数的四丁基氟化铵后的荧光吸收光谱图;
图3是本发明实施例2中探针化合物在乙腈溶液中450nm与500nm荧光强度的比值(I450/I500)和F-摩尔浓度与探针化合物a摩尔浓度比值([F-]/[a])的工作曲线。
具体实施方式
下面通过具体实施例详述本发明,但不限制本发明的保护范围。如无特殊说明,本发明所采用的实验方法均为常规方法,所用实验器材、材料、试剂等均可从化学公司购买。
实施例1
将探针化合物N-3-羟基-4-2’-苯并噻唑苯-3,5-二苯甲氧苯甲酰胺溶于DMSO配成浓度为1×10-3mol/L的溶液A,取30μL溶液A溶于含有3mL乙腈的样品池中,将溶液混合均匀后得到探针化合物的浓度为1×10-5mol/L的混合液B。分别制备含有不同阴离子的乙腈溶液,即四丁基氟化铵乙腈溶液、四丁基磷酸二氢铵乙腈溶液、四丁基硫酸氢铵乙腈溶液、四丁基乙酸铵乙腈溶液和四丁基氯化铵的乙腈溶液,向混合液B中分别加入上述五种溶液,使得加入后四丁基氟化铵的浓度为探针化合物的200倍,其它四种四丁基铵盐的浓度为探针化合物的1000倍,分别测定各溶液在激发波长为370nm的荧光光谱(如图1)。从图1可以看出,探针化合物对AcO-的响应非常弱,H2PO4 -、HSO4 -和Cl-都不能引起探针化合物的荧光光谱的变化,而只有F-在500nm处荧光发射峰猝灭的同时,在450nm处出现了新峰,呈现出比率荧光的特征。以上结果说明探针化合物作为F-的荧光探针具有很好的选择性。
实施例2
将探针化合物N-3-羟基-4-2’-苯并噻唑苯-3,5-二苯甲氧苯甲酰胺溶于DMSO配成浓度为1×10-3mol/L的溶液A,取30μL溶液A溶于含有3mL乙腈的样品池中,将溶液混合均匀后得到探针化合物的浓度为1×10-5mol/L的混合液B,向混合液B中逐步滴加四丁基氟化铵的乙腈溶液,使得加入后四丁基氟化铵的浓度分别是探针化合物的2,5,10,50,80,100,150,200,230倍,分别测定每次滴加后激发波长为370nm的荧光光谱(如图2)。随着氟离子浓度的增加,荧光光谱上500nm处荧光峰强度逐渐减弱,而在450nm处出现了一个新峰,且荧光峰强度逐渐增强,以450nm与500nm荧光强度的比值(I450/I500)为纵坐标,F-浓度与探针化合物浓度比值([F-]/[a])为横坐标做工作曲线,如图3所示,趋势线方程为:I450/I500=0.0012[F-]/[a]+0.0562(R2=0.9938)。
以上所述,仅为本发明创造较佳的具体实施方式,但本发明创造的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明创造披露的技术范围内,根据本发明创造的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明创造的保护范围之内。
Claims (3)
1.一种用于检测氟离子的探针化合物,其特征在于,氟离子探针化合物的化学名称为N-3-羟基-4-2’-苯并噻唑苯-3,5-二苯甲氧苯甲酰胺,结构式如下:
2.权利要求1所述的氟离子探针化合物检测氟离子的方法,其特征在于,具体步骤为:
(1)将探针化合物溶于DMSO配成浓度为1×10-3mol/L的溶液,取30μL上述溶液溶于含有3mL乙腈的样品池中,将溶液混合均匀后得到探针化合物的浓度为1×10-5mol/L的混合液;
(2)向上述混合液中滴加四丁基氟化铵的乙腈溶液,并逐渐加大浓度,使得加入后四丁基氟化铵的浓度分别是探针化合物的2,5,10,50,80,100,150,200,230倍,分别测定每次滴加后激发波长为370nm的荧光光谱,以450nm与500nm荧光强度的比值I450/I500为纵坐标,氟离子浓度与探针化合物浓度比值[F-]/[a]为横坐标做工作曲线;
工作曲线为:I450/I500=0.0012[F-]/[a]+0.0562(R2=0.9938)。
3.根据权利要求2所述的氟离子探针化合物检测氟离子的方法,其特征在于,溶液中还可以存在AcO-、H2PO4 -、HSO4 -和Cl-。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811377135.4A CN109265412B (zh) | 2018-11-19 | 2018-11-19 | 一种用于检测氟离子的探针化合物及其检测方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811377135.4A CN109265412B (zh) | 2018-11-19 | 2018-11-19 | 一种用于检测氟离子的探针化合物及其检测方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109265412A true CN109265412A (zh) | 2019-01-25 |
CN109265412B CN109265412B (zh) | 2020-06-02 |
Family
ID=65189947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811377135.4A Active CN109265412B (zh) | 2018-11-19 | 2018-11-19 | 一种用于检测氟离子的探针化合物及其检测方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109265412B (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004093652A2 (en) * | 2003-04-22 | 2004-11-04 | Molecular Technologies, Inc. | System and method for synthesis of molecular imaging probes including fdg |
CN101626765A (zh) * | 2006-06-23 | 2010-01-13 | 帕拉特克药品公司 | 转录因子调节化合物及其使用方法 |
CN102250134A (zh) * | 2010-05-21 | 2011-11-23 | 中国科学院化学研究所 | 一种识别氟离子的荧光探针及其制备方法和用途 |
CN102469788A (zh) * | 2009-06-30 | 2012-05-23 | 西佳技术公司 | 登革病毒感染的治疗和预防 |
CN102925136A (zh) * | 2012-10-23 | 2013-02-13 | 大连大学 | 一种Zn2+比率荧光探针化合物和制备方法及应用 |
CN103467410A (zh) * | 2013-07-17 | 2013-12-25 | 大连大学 | 一种醋酸根荧光探针化合物及其应用 |
-
2018
- 2018-11-19 CN CN201811377135.4A patent/CN109265412B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004093652A2 (en) * | 2003-04-22 | 2004-11-04 | Molecular Technologies, Inc. | System and method for synthesis of molecular imaging probes including fdg |
CN101626765A (zh) * | 2006-06-23 | 2010-01-13 | 帕拉特克药品公司 | 转录因子调节化合物及其使用方法 |
CN102469788A (zh) * | 2009-06-30 | 2012-05-23 | 西佳技术公司 | 登革病毒感染的治疗和预防 |
CN102250134A (zh) * | 2010-05-21 | 2011-11-23 | 中国科学院化学研究所 | 一种识别氟离子的荧光探针及其制备方法和用途 |
CN102925136A (zh) * | 2012-10-23 | 2013-02-13 | 大连大学 | 一种Zn2+比率荧光探针化合物和制备方法及应用 |
CN103467410A (zh) * | 2013-07-17 | 2013-12-25 | 大连大学 | 一种醋酸根荧光探针化合物及其应用 |
Non-Patent Citations (1)
Title |
---|
吴玉防等: "4-AHBA为核的聚芳醚树枝状化合物的合成及其光学性能", 《合成化学》 * |
Also Published As
Publication number | Publication date |
---|---|
CN109265412B (zh) | 2020-06-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102925136B (zh) | 一种Zn2+比率荧光探针化合物和制备方法及应用 | |
CN103412034A (zh) | 微波消解/icp-ms法快速检测烟草中重金属含量的测定方法 | |
Elabd et al. | Spectroflourimetric assessment of UO22+ by the quenching of the fluorescence intensity of Clopidogrel embedded in PMMA matrix | |
CN103880853A (zh) | 罗丹明6g酰肼衍生物、其制备方法、应用及作为荧光探针对次氯酸进行荧光分析的方法 | |
CN113121513B (zh) | 一种咔唑-香豆素基腙类化合物及其制备方法和用途 | |
CN106905538A (zh) | 一种含锌金属有机框架材料及其制备方法和应用 | |
CN104418874A (zh) | 一种水溶液中检测氟离子荧光分子探针及其合成与应用 | |
CN106442515A (zh) | 一种简单低成本的银离子目视定量检测方法 | |
Aziz et al. | Detection of trace amounts of Hg2+ in different real samples based on immobilization of novel unsymmetrical tetradentate Schiff base within PVC membrane | |
CN111039972B (zh) | 4-羟基咔唑类化合物作为氟离子荧光探针的应用 | |
CN110484242B (zh) | 一种检测水中三价铁离子的荧光探针及其制备和检测方法 | |
CN109738412B (zh) | 一种饮用水中铝、铁、铬、汞、铕、铥和镱离子的检测方法 | |
CN107417681A (zh) | 一种含有香豆素‑噻二唑基席夫碱荧光探针化合物及其制备方法和用途 | |
CN113087651B (zh) | 一种含有吲哚基团的化合物及其制备方法和应用 | |
Abdel Aziz et al. | A Novel Fluorimetric Bulk Optode Membrane Based on NOS Tridentate Schiff Base for Selective Optical Sensing of Al 3+ Ions | |
CN104132920A (zh) | 一种荧光猝灭测定Ag+或F-的方法 | |
CN109293651B (zh) | 一种水溶液中检测锌离子的比率荧光探针化合物及其检测方法 | |
CN109265412A (zh) | 一种用于检测氟离子的探针化合物及其检测方法 | |
CN110057792A (zh) | 一种基于荧光石墨烯量子点的氟离子检测方法 | |
CN109574921B (zh) | 一种检测醋酸根离子的荧光探针及其制备方法和使用方法 | |
CN112345505B (zh) | 四(4-氨基联苯基)乙烯检测次氯酸根的方法及应用 | |
CN108169196B (zh) | 一种快速检测环境中氟离子的方法 | |
CN109608472B (zh) | 一种水溶性超分子荧光探针及其制备和应用 | |
Li et al. | Rational design of piperidine functionalized boron–dipyrromethene as fluorescent chromoionophore for ion-selective optodes | |
CN103467410B (zh) | 一种醋酸根荧光探针化合物及其应用 |
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: 20190125 Assignee: Dalian Youke Instrument Co.,Ltd. Assignor: DALIAN University Contract record no.: X2023210000248 Denomination of invention: A probe compound for detecting fluoride ions and its detection method Granted publication date: 20200602 License type: Common License Record date: 20231129 |
|
OL01 | Intention to license declared | ||
OL01 | Intention to license declared |