CN103254891A - Mercury ion fluorescence sensor as well as synthetic method and application thereof - Google Patents
Mercury ion fluorescence sensor as well as synthetic method and application thereof Download PDFInfo
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- CN103254891A CN103254891A CN2013101636999A CN201310163699A CN103254891A CN 103254891 A CN103254891 A CN 103254891A CN 2013101636999 A CN2013101636999 A CN 2013101636999A CN 201310163699 A CN201310163699 A CN 201310163699A CN 103254891 A CN103254891 A CN 103254891A
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Abstract
The invention discloses a mercury ion fluorescence sensor shown in a formula (I). The sensor comprises a rhodamine b framework, anion bonding unit urea or thiourea and a signal element fluorescent molecular radical sensed. The invention further discloses a synthetic method of the mercury ion fluorescence sensor. The invention further provides an application of the mercury ion fluorescence sensor show in the formula (I) in mercury ion detection. Compared with the prior art, the raw materials used by the invention are available, the synthetic steps are simple and the post-treatment is convenient, and industrialized production is easy to realize.
Description
Technical field
The invention belongs to biological chemistry material field, be specifically related to a kind of mercury ion fluorescent sensor and synthetic method and application.
Background technology
Mercury and compound thereof are a kind of heavy metals of serious harm HUMAN HEALTH, owing to have persistence, easily transport property and biomagnification highly, make it become one of the most noticeable environmental pollutant in the present whole world.Mercury ion can be accumulated in vivo, by food chain transport in human body.The Trace Mercury of accumulation can't be drained by self metabolism in the human body, will directly cause heart, liver, thyroid disease, causes neurological disorder, chronic mercury poisoning, even the formation of initiation malignant tumour.In view of mercury poisoning can produce extremely ill effect to entire society, on global environment supervisory system inventory, the whole world all spends great amount of manpower and material resources and financial resources in the method for the novel detection mercury ion of R and D to mercury by dominated column.
Atomic fluorescence elder generation method particularly Cold Atomic Fluorescent Mercury light method has application (Tao Shu peak, environmental science Leader, 2008,27,89.) more widely in present showing in the ion detection.Liao Lifu (what is rich, Liao Lifu, and lion advances Gao Shuqin, Xiao Xidong recklessly. analytical chemistry, 2009,37,123.) wait general through having reported that a kind of catalysis precipitation wireless sensing method detects trace and shows ion.But show in the detection method of ion existing, always be difficult to get rid of the interference that has closely with other ions of charge distribution and volume.
Advantages such as fluorescence chemical sensor is good, highly sensitive owing to its selectivity, the time of response is fast, the present extensive concern that in the trace detection of mercury ion, has been subjected to people.Design for the fluorescence chemical sensor of most of mercury ions, mainly comprise two parts: one is the luminous group that exports fluorescent signal, another is receptor, usually contain ligating atoms such as nitrogen or sulphur, can strong effect take place with mercury ion, to reach the purpose that detects mercury ion.Oneself is widely used the rhodamine compounds aspect the biotechnology as fluorescent marker, and the principle of design of this class sensor molecule is: metal ion by with the coordination of acceptor, induced the formation of look down limb open loop structure in the volution.According to the identification of this process realization to ion, such advantage is arranged: when sensor molecules has recognition reaction to metal ion, not only make to absorb and intensity of fluorescence has bigger enhancing, and solution is occurred by colourless to coloured variation, this process can realize easily that naked eyes identify.
Be used for detecting the chemical sensor that shows ion at present; all there are some problems in actual applications in great majority, and are very long such as the synthetic route of fluorescent optical sensor, are not suitable for large-scale production; the metal ion of various competitions makes its application be subjected to certain restriction to the interference measured etc.
Summary of the invention
The present invention overcomes the above-mentioned deficiency of prior art, proposes that a kind of synthesis step is simple and convenient, good biocompatibility, has high-sensitive mercury ion fluorescent chemical sensor and the synthetic method thereof of particular optical response.
Mercury ion fluorescent sensor of the present invention comprises the rhodamine B skeleton, the strong signal element fluorescence molecule group of unit urea or thiocarbamide and sensing thereof that closes of negatively charged ion.The structure of mercury ion fluorescent sensor of the present invention, as with shown in the following formula (I):
Wherein, A is O, S, and R is to trifluoromethylbenzene.
The present invention also provides a kind of synthetic method of mercury ion fluorescent sensor; rhodamine B and excessive hydrazine hydrate be the hydrazinolysis reaction in organic solvent; the intermediate that aforementioned hydrazinolysis reaction is obtained is dissolved in the organic solvent; under the N2 protection; add isocyanic ester; the reaction solution that obtains obtains the described mercury ion fluorescent sensor of purpose product after suction filtration, drying.
The synthetic method of mercury ion fluorescent sensor of the present invention; compared with prior art; its route is short; the reaction conditions gentleness does not all have the hydrazinolysis reaction in organic solvent of high temperature rhodamine B and excessive hydrazine hydrate in the synthetic process, the intermediate that aforementioned hydrazinolysis reaction is obtained is dissolved in the organic solvent; under the N2 protection; add isocyanic ester, the reaction solution that obtains obtains the described mercury ion fluorescent sensor of purpose product after suction filtration, drying.The synthetic route of mercury ion fluorescent sensor of the present invention is as follows:
In the synthetic method of the present invention, described organic solvent is ethanol, methyl alcohol, methylene dichloride or N, dinethylformamide.
The present invention also provides the application of the mercury ion fluorescent sensor shown in a kind of formula (I) in mercury ion fluorescent detects.
During the present invention used, the mercury ion fluorescent sensor can also optionally detect mercury ion.
During the present invention used, the mercury ion fluorescent sensor can also be used for the detection of mercury ion in cell simultaneously.
Compared with prior art; synthetic method of the present invention by the different organic solvent of screening can be simply, the hydrazinolysis intermediate of one-step synthesis rhodamine B; and then the rhodamine B derivative of synthetic a series of different structures accordingly; the raw material that the inventive method is used is easy to get; synthesis step is simple, is conducive to accomplish scale production.
Description of drawings
Fig. 1 is the nucleus magnetic resonance figure of rhodamine B hydrazine hydrolysis products of the present invention
1H NMR;
Fig. 2 is the product nucleus magnetic resonance figure of embodiments of the invention 2
1HNMR
13C NMR;
Fig. 3 is the product nucleus magnetic resonance figure of embodiments of the invention 3
1HNMR
13C NMR;
Fig. 4 is the product uv-absorbing titration curve of embodiments of the invention 2;
Fig. 5 is the product fluorometric titration curve of embodiments of the invention 2;
Fig. 6 is the product ion selectivity lab diagram of embodiments of the invention 2;
Fig. 7 is the product cell imaging figure of embodiments of the invention 2;
Fig. 8 is the product uv-absorbing titration curve of embodiments of the invention 3;
Fig. 9 is the product fluorometric titration curve of embodiments of the invention 3;
Figure 10 is the product ion selectivity lab diagram of embodiments of the invention 3;
Figure 11 is the product cell imaging figure of embodiments of the invention 3.
Embodiment
In conjunction with following specific embodiments and the drawings, the present invention is described in further detail, and protection content of the present invention is not limited to following examples.Under the spirit and scope that do not deviate from inventive concept, variation and advantage that those skilled in the art can expect all are included in the present invention, and are protection domain with the appending claims.Implement process of the present invention, condition, reagent, experimental technique etc., except the following content of mentioning specially, be universal knowledege and the common practise of this area, the present invention is not particularly limited content.
The synthetic method of mercury ion fluorescent sensor of the present invention, concrete steps comprise as follows:
The preparation of step (1) intermediate:
Rhodamine B and excessive hydrazine hydrate are in organic solvent, and the control temperature of reaction is at 50-120 ℃, and the reaction times is the rhodamine B after 24-40h obtains hydrazinolysis;
Wherein, the structural formula of rhodamine B is:
Wherein, the intermediate that obtains of step (1) is that the structural formula of the rhodamine B behind the hydrazinolysis is:
Wherein, organic solvent is ethanol, methyl alcohol, methylene dichloride or N, dinethylformamide.
The preparation of step (2) mercury ion fluorescent sensor:
The hydrazinolysis intermediate of the rhodamine B that obtains is dissolved in the organic solvent, and the N2 protection adds the isocyanic ester of equivalent down, and the control temperature of reaction is in room temperature, and the reaction times is 24-40h.After reaction is finished, the reaction solution of gained is poured in the frozen water, suction filtration, drying, obtaining the purpose product is the mercury ion fluorescent sensor shown in the formula (I).
Wherein, A is O, S, and R is to trifluoromethylbenzene.
Wherein, the related organic solvent of step 2 is ethanol, methyl alcohol, methylene dichloride or N, dinethylformamide.
The preparation of the hydrazinolysis product (intermediate) of embodiment 1 rhodamine B:
In the glass flask of 250mL, the 20g rhodamine B is dissolved in fully in the ethanol of 100mL, control temperature at 100 ℃, backflow 24h.Removal of solvent under reduced pressure is poured in the frozen water then, filters drying.Obtain the solid 18.7g of white, productive rate 98%.The nuclear-magnetism phenogram is seen Fig. 1.
Nuclear-magnetism characterize 1H NMR (500MHz, DMSO) δ 1.09 (t, J=6.7Hz, 12H), 3.31 (q, J=19.7Hz, 8H), 4.19 (br, 2H), 6.34 (br, 4H), 6.38 (br, 2H), 6.98 (d, J=6.5Hz, 1H), 7.46 (t, J=3.6Hz, 2H), 7.75 (d, J=6.7Hz, 1H).
The preparation (F1) of embodiment 2 mercury ion fluorescent sensors 1:
In the glass flask of 250mL, 5g rhodamine B hydrazinolysis is dissolved in the N of 50mL fully, in the dinethylformamide solution, under the N2 protection, add equivalent to the trifluoromethylbenzene isocyanic ester, the control temperature is at stirring at room 2h.Then reaction solution is poured in a large amount of frozen water, filtered drying.Obtain F16.8g, productive rate 97%.F1 nuclear-magnetism phenogram and carbon spectrum phenogram are seen Fig. 2.
Nuclear-magnetism characterizes
1H NMR (500MHz, DMSO) δ 0.85 (br, 12H), 3.28 (q, J=3.4Hz, 8H), 6.32 (d, J=5.25Hz, 4H), 6.33 (s, 2H), 7.04 (d, J=7.25Hz, 1H), 7.46-7.60 (m, 6H), 7.85 (d, J=7.15Hz, 1H), 8.21 (s, 1H).
The carbon stave is levied
13C NMR (500MHz, DMSO) δ 12.9,44.6, and 68.2,97.7,106.5,114.3,121.9,124.1,125.3,128,128.3,128.8,129.2,131.3,139.5,132.1,132.6,142.7,149.4,151.9,153.8,160.8.
HRMS (ESI) C
36H
37F
3N
5O
3[M+H]
+=644.2839, theoretical value is 644.2843.
The preparation (F2) of embodiment 3 mercury ion fluorescent sensors 2:
In the glass flask of 250mL, 5g rhodamine B hydrazinolysis is dissolved in the N of 50mL fully, in the dinethylformamide solution, at N
2Protection add down equivalent to the trifluoromethyl PhNCS, the control temperature is at stirring at room 2h.Then reaction solution is poured in a large amount of frozen water, filtered drying.Obtain F217.lg, productive rate 98%.F2 nuclear-magnetism phenogram and carbon spectrum phenogram are seen Fig. 3.
Nuclear-magnetism characterizes
1H NMR (500MHz, DMSO) δ 1.06 (br, 12H), 3.28 (q, J=7.645Hz, 8H), 6.08 (s, 2H), 6.32 (s, 3H), 6.97 (s, 1H), 7.12 (d, J=7.29Hz1H), 7.48 (t, J=10.725Hz, 3H), 7.60 (m, 4H), 7.91 (d, J=7.25Hz, 1H), 9.02 (s, 1H), 9.77 (s, 1H).
The carbon stave is levied
13C NMR (500MHz, DMSO) δ 12.9,44.6, and 68.2,97.7,106.5,114.3,121.9,124.1,125.3,128,128.3,128.8,129.2,131.3,139.5,132.1,132.6,142.7,149.4,151.9,153.8,160.8.
HRMS (ESI) C
36H
37F
3N
5O
2S[M+H]
+660.2596 theoretical value is 660.2615.
Accurately the concentration of configuration fluorescence chemical sensor 1 (F1) is 2 * 10
-5Mol/L and 1 * 10
-5Mol/L, the concentration of mercury ion is respectively 4 * 10
-2Mol/L and 2 * 10
-2Mol/L.Adopt ultraviolet-visible spectrophotometry and fluorophotometric method to investigate the titration situation of 1 pair of mercury ion of fluorescence chemical sensor.The ultraviolet titration experiments is seen shown in Figure 4, the concentration C of fluorescence chemical sensor 1
F1=2 * 10
-5M, ion concentration of mercury C
Hg2+=4 * 10
-2M is as no Hg
2+Add fashionablely, ultraviolet absorptivity is 0, increases Hg gradually
2+Equivalent, ultraviolet absorptivity increases gradually, works as Hg
2+When reaching 70 equivalents, the constant maximum value that reaches of absorbancy illustrates that this probe can detect Hg
2+The fluorometric titration experiment is seen shown in Figure 5, C
F1=1 * 10
-5M, C
Hg2+=2 * 10
-2M is along with Hg
2+Be increased to the process of 40 equivalents from 0 equivalent, probe has experienced by no fluorescence to the process that fluorescence is arranged, and the last constant maximum value that reaches of fluorescence intensity, further specifies this probe and can detect Hg
2+
Accurately the concentration of configuration fluorescence chemical sensor 1 (F1) is 1 * 10
-5Mol/L, metal ion Na
+, K
+, Zn2+, Ca
2+, Mg
2+, Ni
2+, Cd
2+, Ag
+, Cu
2+, Hg
2+Isoconcentration is 2 * 10
-2Mol/L when the amount of substance of metal ion is 40 times of amount of fluorescent probe, investigates fluorescence chemical sensor to the property the selected identification of ion.Experimental result is seen shown in Figure 6, as can be seen from the figure 1 couple of Zn of probe
2+, Mg
2+, Ag
+Very weak even do not have Deng metal-ion fluorescent response, to Hg
2+During special response, prove that probe 1 can be used as Hg
2+Efficient sensor and be not subjected to the interference of other ions.
Accurately the concentration of configuration fluorescence chemical sensor 1 (F1) is 5 * 10
-5The concentration of mol/L and mercury ion is 2 * 10
-2Mol/L investigates fluorescent probe 1 identification experiment to mercury ion on cell levels.Concrete enforcement is as follows, and probe 1 is cultivated 1h with lewis lung cell in 37 ℃ of constant incubators after, the PBS damping fluid is removed extracellular probe 1, adds Hg then
2+Cultivate 1h altogether.
The fluorescence co-focusing microscopically is taken pictures, and can see that cell sends very strong fluorescence, proves that probe can enter cell, and detect Hg in cell
2+Experimental result is seen shown in Figure 7, a: cell imaging picture under the visible light; B: add cell imaging picture under the fluorescence after fluorescent probe F1 cultivates 1h; C: add fluorescent probe F1 and cultivate 1h, after add Hg again
2+Cell imaging picture under the fluorescence behind the cultivation 1h.
Accurately the concentration of configuration fluorescence chemical sensor 2 (F2) is 1 * 10
-5Mol/L, the concentration of mercury ion is 2 * 10
-3Mol/L.Adopt ultraviolet-visible spectrophotometry and fluorophotometric method to investigate the titration situation of 2 pairs of mercury ions of fluorescence chemical sensor.The ultraviolet titration experiments is seen shown in Figure 8, the concentration C of fluorescence chemical sensor 1
F1=1 * 10
-5M, ion concentration of mercury C
Hg 2+=2 * 10
-3M, along with the increase of ion concentration of mercury, the uv-absorbing of fluorescent probe F2 strengthens, and when the amount of mercury ion reached an equivalent, the uv-absorbing of probe F2 reached capacity.The fluorometric titration experiment is seen shown in Figure 9, and similar with the ultraviolet titration, when the concentration of mercury ion reached equivalent, the fluorescence intensity of probe F2 no longer changed.
Investigate the selectivity experiment of the ion of probe F2, specifically implement as followsly, the concentration that the concentration of preparing configuration probe F2 is is 1 * 10
-5Mol/L, metal ion Na
+, K
+, Zn2+, Ca
2+, Mg
2+, Ni
2+, Cd
2+, Ag
+, Cu
2+, Hg
2+, Fe
3+Isoconcentration is 2 * 10
-2Mol/L.Concrete enforcement is as follows, and the amount of measuring ion respectively is 10 times and the fluorescence intensity of coexisting ion (10 times of amounts of 10 times of amounts of other ion and mercury ion) of probe F2.Experimental result is seen Figure 10, and from result of experiment, other metal ion is very little to the influence of mercury ion, can know by inference thus, and probe F2 is, and mercury ion has selectivity.
Investigate probe F2 in the identification level of cell levels to mercury ion, experimental result as shown in figure 11.Concrete enforcement is as follows, and the concentration that accurately disposes probe F2 is that the concentration of 5 * 10-5mol/L and mercury ion is 2 * 10-2mol/L.Probe F2 and lewis lung cell cultivated 1h in 37 ℃ of constant incubators after, the PBS buffering is removed extracellular probe F2, so adds Hg2 and cultivates 1h.The fluorescence co-focusing microscopically is taken pictures, and experimental result shows, the more about probe F1 of the fluorescence intensity after probe F2 and the mercury ion effect.Prove that thus probe F2 can enter cell, and in cell, detect Hg
2+Effect be better than probe F1.A: cell imaging picture under the visible light; B: add cell imaging picture under the fluorescence after fluorescent probe 2 is cultivated 1h; C: add fluorescent probe 2 and cultivate 1h, after add Hg again
2+Cell imaging picture under the fluorescence behind the cultivation 1h;
Find that from experimental result probe F1, F2 both can reach efficient detection Hg
2+Purpose, wherein the detection of F2 response will be higher than F1, illustrates that the sensor detection efficiency based on devulcanization mercury mechanism is preferred.
Claims (6)
1. a mercury ion fluorescent sensor is characterized in that, the structure of described mercury ion fluorescent sensor is as with shown in the following formula (I):
Wherein, A is O, S, and R is to trifluoromethylbenzene.
2. the synthetic method of a mercury ion fluorescent sensor; it is characterized in that; rhodamine B and excessive hydrazine hydrate be the hydrazinolysis reaction in organic solvent; the intermediate that aforementioned hydrazinolysis reaction is obtained is dissolved in the organic solvent; under the N2 protection; add isocyanic ester, the reaction solution that obtains obtains the described mercury ion fluorescent sensor of purpose product after suction filtration, drying.
3. synthetic method as claimed in claim 2 is characterized in that, described organic solvent is ethanol, methyl alcohol, methylene dichloride or N, dinethylformamide.
4. the application of mercury ion fluorescent sensor in mercury ion fluorescent detects.
5. the application of mercury ion fluorescent sensor as claimed in claim 4 in mercury ion fluorescent detects is characterized in that, the alternative mercury ion that detects.
6. the application of mercury ion fluorescent sensor as claimed in claim 4 in mercury ion fluorescent detects is characterized in that, can be used for the detection of mercury ion in cell simultaneously.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104140432A (en) * | 2014-07-17 | 2014-11-12 | 苏州大学 | Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof |
| CN105131004A (en) * | 2015-09-17 | 2015-12-09 | 华南师范大学 | 1-naphthyl isothiocyanate modified rhodamine B derivative, preparation method and application |
| KR101612117B1 (en) * | 2014-12-01 | 2016-04-12 | 한국생명공학연구원 | Composition for use in selectively detecting mercury ion and portable mercury ion detection sensor |
| CN105670609A (en) * | 2016-02-29 | 2016-06-15 | 江苏大学 | Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe |
| CN105801589A (en) * | 2016-04-05 | 2016-07-27 | 江苏省原子医学研究所 | Rhodamine 6G derivative based colorimetric probes as well as preparation method and application thereof |
| CN106117230A (en) * | 2016-06-29 | 2016-11-16 | 河南师范大学 | Replace rhodamine B amide groups Thiourea fluorescent probe compounds and its preparation method and application |
| CN106220640A (en) * | 2016-06-29 | 2016-12-14 | 河南师范大学 | One class mercury ion fluorescence probe and its preparation method and application |
| CN109239026A (en) * | 2018-01-23 | 2019-01-18 | 齐齐哈尔大学 | A kind of phosphinylidyne-containing amine group fluorescence probe is to Hg2+Fluorescence detection and application method |
| CN112521365A (en) * | 2020-11-06 | 2021-03-19 | 吉林大学 | Phenanthrene ketal with novel structure and degradation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102942919A (en) * | 2012-11-13 | 2013-02-27 | 山东大学 | Application of rhodamine B thio-bishydrazide derivative as Hg<2+> fluorescent probe |
-
2013
- 2013-05-06 CN CN2013101636999A patent/CN103254891A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942919A (en) * | 2012-11-13 | 2013-02-27 | 山东大学 | Application of rhodamine B thio-bishydrazide derivative as Hg<2+> fluorescent probe |
Cited By (13)
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| CN104140432A (en) * | 2014-07-17 | 2014-11-12 | 苏州大学 | Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof |
| KR101612117B1 (en) * | 2014-12-01 | 2016-04-12 | 한국생명공학연구원 | Composition for use in selectively detecting mercury ion and portable mercury ion detection sensor |
| CN105131004A (en) * | 2015-09-17 | 2015-12-09 | 华南师范大学 | 1-naphthyl isothiocyanate modified rhodamine B derivative, preparation method and application |
| CN105670609B (en) * | 2016-02-29 | 2018-10-09 | 江苏大学 | A kind of novel Rhodamine fluorescent probe and preparation method thereof of detection mercury ion |
| CN105670609A (en) * | 2016-02-29 | 2016-06-15 | 江苏大学 | Novel rhodamine fluorescent probe for detecting mercury ions, and preparation method of novel rhodamine fluorescent probe |
| CN105801589A (en) * | 2016-04-05 | 2016-07-27 | 江苏省原子医学研究所 | Rhodamine 6G derivative based colorimetric probes as well as preparation method and application thereof |
| CN106117230A (en) * | 2016-06-29 | 2016-11-16 | 河南师范大学 | Replace rhodamine B amide groups Thiourea fluorescent probe compounds and its preparation method and application |
| CN106220640A (en) * | 2016-06-29 | 2016-12-14 | 河南师范大学 | One class mercury ion fluorescence probe and its preparation method and application |
| CN106220640B (en) * | 2016-06-29 | 2018-06-01 | 河南师范大学 | A kind of mercury ion fluorescence probe and its preparation method and application |
| CN106117230B (en) * | 2016-06-29 | 2018-07-06 | 河南师范大学 | Replace rhodamine B amide groups Thiourea fluorescent probe compounds and its preparation method and application |
| CN109239026A (en) * | 2018-01-23 | 2019-01-18 | 齐齐哈尔大学 | A kind of phosphinylidyne-containing amine group fluorescence probe is to Hg2+Fluorescence detection and application method |
| CN109239026B (en) * | 2018-01-23 | 2021-04-06 | 齐齐哈尔大学 | Amide group-containing fluorescent probe for Hg2+And methods of use |
| CN112521365A (en) * | 2020-11-06 | 2021-03-19 | 吉林大学 | Phenanthrene ketal with novel structure and degradation method thereof |
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Inventor after: Liu Shunying Inventor after: Xie Yegui Inventor after: Wang Dongwei Inventor after: Wu Xianrong Inventor before: Liu Shunying Inventor before: Xie Yegui Inventor before: Wang Dongwei Inventor before: Wu Xianrong |
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Application publication date: 20130821 |