CN105331358A - Dirhodamine-based Sn4+ fluorescent probe molecule and preparation method and application thereof - Google Patents
Dirhodamine-based Sn4+ fluorescent probe molecule and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a preparation method for a high-selectivity Sn4+ fluorescent probe based on a dirhodamine-ethanolamine derivative. Rhodamine B and ethanolamine are subjected to condensed acylation reaction to obtain a rhodamine-ethanolamine derivative, and the rhodamine-ethanolamine derivative and isophthaloyl dichloride are subjected to reaction to obtain the dirhodamine-contained Sn4+ fluorescent probe-SnP1. The probe shows good selectivity in a system where Sn4+ and other metal ions coexist, has the advantages of high sensitivity, fast response, reversible operation and the like, and can be well applied to detection of Sn4+ in an environment.
Description
Technical field
The present invention relates to a kind of tin ion (Sn
4+) detection agent, be specifically related to a kind of Sn based on two rhodamine
4+the preparation method of fluorescent probe.
Background technology
Tin is extensively present in air, soil and water at present, is one of heavy metal common in industry.Since the Industrial Revolution, increasing inorganic tin and organotin are introduced in environment.Tin is the trace element of needed by human, and at suprarenal gland, liver, brain, in the organ such as spleen and Tiroidina, content is maximum.The shortage of tin may cause poor growth and hearing disability, and tin take part in somatomedin and preventing cancer to have some evidences to show.Meanwhile, because tin is widely used in the field such as agricultural, industry, tin also becomes one of heavy metal contaminants common in environment.The excessive tin of absorption of human body also can cause important impact to health.The symptom of tin poisoning is limited to gastrointestinal reaction mostly as felt sick, stomachache, vomiting etc.Therefore, studying one can rapid detection Sn
4+method tool be of great significance.
Fluorescent probe have selectivity good, highly sensitive, easy and simple to handle fast, to be widely used in metallic cation in testing environment and living things system, negatively charged ion, organism the aspects such as active small molecular to detecting the advantages such as thing damage is few.The development and utilization research of fluorescent probe molecule is the crossing domain of the science such as chemistry and biology, medical science, agricultural.Fluorescent probe technique is on a molecular scale to the analytical procedure that research object is studied.Fluorescent probe has been widely used in the detection of the material such as heavy metal, bioactive small molecule in environmental and biological materials at present.
It is wide and to the advantage such as pH value stable range is wide that dye stuff of rhodamine kinds has larger molar absorptivity, high, the good optical stability of fluorescence quantum yield, wavelength region, has been widely used in the Design and synthesis of fluorescent probe.Rhodamine derivative is used to be designed to fluorescent probe in order to detect metallic cation in organism or environment or negatively charged ion in recent years.The mechanism of rhodamine fluorescence probe identification metal ion as shown in the figure.The Rhodamine Derivatives of Guan Huan itself does not have color and fluorescence, but makes lactan volution in its molecule open when adding corresponding metallic cation or negatively charged ion, and solution can become pink from colourless, discharges stronger fluorescence simultaneously.
Summary of the invention
The object of this invention is to provide a kind of Sn based on two rhodamine
4+the preparation method of fluorescent probe.
A kind of Sn based on two rhodamine that the present invention proposes
4+the preparation method of fluorescent probe, first carries out condensation acylation reaction by commercial rhodamine B and thanomin, obtains a kind of rhodamine B-ethanolamine derivant; This rhodamine B-ethanolamine derivant and m-phthaloyl chloride carry out acyl chloride reaction and obtain a kind of compound containing two rhodamine B, and this compound can be used as Sn in methanol-water solution
4+highly selective fluorescent probe.
A kind of Sn based on two rhodamine that the present invention proposes
4+the preparation method of fluorescent probe, its concrete synthetic route is as follows:
(1) by rhodamine B and thanomin, stirring and refluxing in ethanolic soln is extremely fully reacted, the completely rear cooling reaction system of question response is to room temperature, removal of solvent under reduced pressure, again dissolve by ethyl acetate, with pure water and saturated nacl aqueous solution washing, organic phase anhydrous sodium sulfate drying, filters, removal of solvent under reduced pressure, silica gel column chromatography is separated and obtains intermediate product RhB-OH.
(2) intermediate RhB-OH and triethylamine are mixed in dichloromethane solution, the dichloromethane solution of m-phthaloyl chloride is added dropwise under condition of ice bath, it should be room temperature reaction after dropwising, after reacting completely, saturated nacl aqueous solution washs, organic phase anhydrous sodium sulfate drying, filter, removal of solvent under reduced pressure, with ethyl acetate and sherwood oil as washing composition, is separated through silica gel column chromatography and obtains product S nP1.
In described step (1), rhodamine B is 1:4 with the ratio of the amount of substance of thanomin, and described reflux temperature is 80-90 DEG C, and the reaction times is 8-15 hour.
In described step (1), the elutriant that silicagel column is separated is CH
2cl
2and CH
3oH, described CH
2cl
2with CH
3the volume ratio of OH is 10-18:1, and productive rate is 60-85%.
In described step (2), compound R hB-OH is 2-4 equivalent, and m-phthaloyl chloride is 1 equivalent, and triethylamine is 2-5 equivalent, and the room temperature reaction time is 6-10h.
In described step (2), the elutriant that silicagel column is separated is CH
2cl
2and CH
3oH, described CH
2cl
2with CH
3the volume ratio of OH is 10-20:1, and productive rate is 60-75%.
Based on the Sn of two rhodamine
4+fluorescent probe molecule is at detection Sn
4+in application.
Accompanying drawing explanation
Fig. 1 is fluorescent probe SnP1 hydrogen nuclear magnetic resonance spectrogram of the present invention;
Fig. 2 is fluorescent probe SnP1 carbon-13 nmr spectra figure of the present invention;
Fig. 3 is fluorescent probe SnP1 high resolution mass spectrum figure of the present invention;
Fig. 4 is fluorescent probe SnP1 fluorescence selectivity figure, excitation wavelength 520nm of the present invention;
Fig. 5 is that fluorescent probe SnP1 of the present invention identifies Sn
4+anti-metal Cation Interferences figure, excitation wavelength 520nm, emission wavelength 577nm;
Fig. 6 is that fluorescent probe SnP1 of the present invention identifies Sn
4+anti-negatively charged ion interference figure, excitation wavelength 520nm, emission wavelength 577nm.
Embodiment
The chemical reagent, solvent, metal ion etc. that use in the process of fluorescent probe SnP1 is prepared all purchased from Aladdin Reagent Company in the present invention.At confirmation and the performance test process employing Bruke company DTX-400 type nuclear magnetic resonance spectrometer of fluorescent probe SnP1, solvent is deuterochloroform, take TMS as internal labeling record proton nmr spectra and carbon spectrum.Adopt the Q-ExactiveHR-MS mass spectrograph record high resolution mass spectrum data of Thermo company.Adopt HIT F-7000 fluorescence spectrophotometer record fluorescence spectrum.
The structure of the final product SnP1 of the present invention's synthesis obtains the confirmation of proton nmr spectra, carbon spectrum and high resolution mass spectrum.
1, the preparation of intermediate RhB-OH:
In the single necked round bottom flask of 100mL, add the hydrochloride (1.00g of rhodamine B, 2.08mmol), thanomin (0.54mL, 8.32mmol) with 50mL ethanol, back flow reaction completely rear (10h) is by reaction solution cool to room temperature, the solid obtained after solvent is removed in decompression is dissolved in the ethyl acetate solution of 30mL, wash with water (30mL × 2) and saturated nacl aqueous solution (30mL × 2), organic phase anhydrous sodium sulfate drying, filter, after removal of solvent under reduced pressure, (elutriant is CH to column chromatography for separation
2cl
2: CH
3oH=10:1, volume ratio) obtain intermediate product RhB-OH, productive rate is 75%.
2, the preparation of probe SnP1:
In the single necked round bottom flask of 100mL, add intermediate RhB-OH (1.21g, 2.5mmol) with triethylamine (0.25g, 2.5mmol) be mixed in anhydrous methylene chloride solution (40mL), m-phthaloyl chloride (0.2g is added dropwise under condition of ice bath, anhydrous methylene chloride solution (15mL) 1mmol), it should be room temperature reaction after dropwising, react completely after (about 8h), saturated nacl aqueous solution (30mL × 2) washs, organic phase anhydrous sodium sulfate drying, filters, removal of solvent under reduced pressure, through silica gel column chromatography separation, (elutriant is CH
2cl
2: CH
3oH=15:1, volume ratio) obtain product S nP1, productive rate is 69%.
Nuclear magnetic resonance hydrogen spectruming determining:
1hNMR (CDCl
3, 400MHz) and δ 1.15 (t, J=6.0Hz, 24H), 3.30 (q, J=6.7Hz, 16H), 3.36 (s, 4H), 4.02 (t, J=4Hz, 4H), 6.22 (d, J=8Hz, 4H), 6.37 (s, 4H), 6.46 (d, J=8Hz, 4H), 7.08 (q, J=2.7Hz, 2H), 7.44 (d, J=4Hz, 5H), 7.94 (q, J=2.7Hz, 2H), 8.08 (t, J=4Hz, 2H), 8.46 (s, 1H).
Carbon-13 nmr spectra measures:
13cNMR (CDCl
3, 100MHz) and δ 168.53,165.1,153.9,153.1,148.8,133.7,132.6,130.8,130.6,130.4,128.7,128.4,128.0,123.8,122.9,108.2,105.2,97.8,64.8,62.3,44.3,38.6,12.6.
High resolution mass spectrum measures: HR-ESI-MScalcdforC
68h
73n
6o
8 +: 1101.5484, found1101.5344.
3, the application examples of probe SnP1
The preparation of solution:
Metal inorganic salt: lead nitrate, Silver Nitrate, cadmium nitrate, other are muriate (K
+, Na
+, Ca
2+, Mg
2+, Ba
2+, Zn
2+, Fe
2+, Fe
3+, Mn
2+, Cu
2+, Co
2+, Ni
2+, Hg
2+) and producer is Aladdin Reagent Company or Tianjin Ke Miou Reagent Company.Precise respective metal salt, is dissolved in high purity water the solution for standby preparing 10mM.
The probe solution preparation of 1mM: precise correspondent probe (SnP1), SnP1 is dissolved in methanol solution the solution for standby preparing 1mM.
Fluorescence selectivity is tested:
Fluorescence spectrophotometer is used to test its fluorescence selectivity.As shown in Figure 4, independent probe SnP1 (10 μMs) is at CH
3oH-H
2in O (99/1, v/v) solution, there is faint fluorescent emission intensity, when adding Sn
4+(10 equivalent) afterwards its fluorescent emission intensity obviously strengthens, but when adding other metal ion (100 μMs), only adds Fe
3+, Sn
2+, Cr
3+solution system fluorescence intensity have certain enhancing, but response intensity is lower, and all the other metal ion system fluorescence intensities do not have considerable change.Above experimental result shows, this probe has good single-minded selectivity to mercury ion.
Fluorescence interference is tested:
In order to test probe molecule is to Sn
4+the immunity from interference detected, tests its metallic cation interference and negatively charged ion interference respectively in fluorescence emission spectrum.As shown in Figure 5, at SnP1 (10 μMs) at CH
3oH-H
2the various metallic cations (100 μMs) adding test in O (99/1, v/v) solution respectively test its fluorescent emission intensity (577nm), and then add the Sn of 100 μMs in the solution containing each metal ion species
4+solution, from accompanying drawing 5, add mercury ion when other metallic cations exist substantially identical with the fluorescence intensity (577nm) obtained when adding separately mercury ion, and this result shows that probe SnP1 is to Sn
4+detection there is stronger anti-metal Cation Interferences ability.According to similar method, test it to Common Anions (Cl
-, Br
-, F
-, I
-, CO
3 2-, NO
3 -, PO
4 3-, SO
4 2-) immunity from interference, as shown in Figure 6, probe SnP1 is to Sn
4+detection there is stronger anti-negatively charged ion interference performance.
Claims (7)
1. the Sn based on two rhodamine
4+fluorescent probe molecule, is characterized in that, described fluorescent probe structural formula is as follows:
2. as right 1 require as described in the Sn based on two rhodamine
4+the preparation method of fluorescent probe molecule, is characterized in that: its step is as follows:
(1) rhodamine B and thanomin are stirred in ethanolic soln, reflux is to fully reaction, the completely rear cooling reaction system of question response is to room temperature, removal of solvent under reduced pressure, with acetic acid ethyl dissolution, with pure water and saturated nacl aqueous solution washing, organic phase anhydrous sodium sulfate drying, filter, removal of solvent under reduced pressure, silica gel column chromatography is separated and obtains intermediate product RhB-OH;
(2) intermediate product RhB-OH and triethylamine are mixed in dichloromethane solution, the dichloromethane solution of m-phthaloyl chloride is added dropwise under condition of ice bath, it should be room temperature reaction after dropwising, after reacting completely, saturated nacl aqueous solution washs, organic phase anhydrous sodium sulfate drying, filter, removal of solvent under reduced pressure, with methylene dichloride and methyl alcohol as washing composition, is separated the Sn obtained containing two rhodamine through silica gel column chromatography
4+fluorescent probe molecule SnP1.
3. as claimed in claim 2 based on the Sn of two rhodamine
4+the preparation method of fluorescent probe molecule, is characterized in that: in described step (1), and rhodamine B is 1:4 with the ratio of the amount of substance of thanomin, and described reflux temperature is 80-90 DEG C, and the reaction times is 8-15 hour.
4. as claimed in claim 2 based on the Sn of two rhodamine
4+the preparation method of fluorescent probe molecule, is characterized in that: in described step (1), and the elutriant that silicagel column is separated is CH
2cl
2and CH
3oH, described CH
2cl
2with CH
3the volume ratio of OH is 10-18:1, and productive rate is 60-85%.
5. as claimed in claim 2 based on the Sn of two rhodamine
4+the preparation method of fluorescent probe molecule, is characterized in that: in described step (2), and compound R hB-OH is 2-4 equivalent, and m-phthaloyl chloride is 1 equivalent, and triethylamine is 2-5 equivalent, and the room temperature reaction time is 6-10h.
6. as claimed in claim 2 based on the Sn of two rhodamine
4+the preparation method of fluorescent probe molecule, is characterized in that: in described step (2), and the elutriant that silicagel column is separated is CH
2cl
2and CH
3oH, described CH
2cl
2with CH
3the volume ratio of OH is 10-20:1, and productive rate is 60-75%.
7. based on the Sn of two rhodamine
4+fluorescent probe molecule is at detection Sn
4+in application.
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| CN106478646A (en) * | 2016-09-26 | 2017-03-08 | 西北大学 | A kind of photosensitive probe of rhodamine guanidine radicals benzimidazole functionalization and its application |
| CN110862507A (en) * | 2019-10-29 | 2020-03-06 | 温州大学 | Preparation method of self-recoverable mechanochromic fluorescent water-based polyurethane |
| CN108424419B (en) * | 2018-03-31 | 2020-10-27 | 浙江工业大学 | Chain double 1,2, 3-triazole rhodamine 6G fluorescent probe and preparation and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106478646B (en) * | 2016-09-26 | 2018-10-26 | 西北大学 | A kind of photosensitive probe of rhodamine-guanidine radicals benzimidazole functionalization and its application |
| CN108424419B (en) * | 2018-03-31 | 2020-10-27 | 浙江工业大学 | Chain double 1,2, 3-triazole rhodamine 6G fluorescent probe and preparation and application thereof |
| CN110862507A (en) * | 2019-10-29 | 2020-03-06 | 温州大学 | Preparation method of self-recoverable mechanochromic fluorescent water-based polyurethane |
| CN110862507B (en) * | 2019-10-29 | 2021-12-21 | 温州大学 | Preparation method of self-recoverable mechanochromic fluorescent water-based polyurethane |
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