CN105331358B - A kind of Sn based on double rhodamines4+Fluorescent probe molecule and preparation method and application - Google Patents

A kind of Sn based on double rhodamines4+Fluorescent probe molecule and preparation method and application Download PDF

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CN105331358B
CN105331358B CN201510890121.2A CN201510890121A CN105331358B CN 105331358 B CN105331358 B CN 105331358B CN 201510890121 A CN201510890121 A CN 201510890121A CN 105331358 B CN105331358 B CN 105331358B
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rhodamines
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CN105331358A (en
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张迪
刘继红
尹海燕
王红旗
李淑芳
王敏
马莹
刘冬梅
李漫
贾斌
周玲
张军锋
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Henan Academy of Agricultural Sciences
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Abstract

The present invention relates to a kind of high selectivity Sn based on double rhodamine ethanolamine derivants4+The preparation method of fluorescent probe.Condensation acylation reaction is carried out by rhodamine B and ethanolamine and obtains rhodamine ethanolamine derivant, rhodamine ethanolamine derivant is obtained into the Sn containing double rhodamines with m-phthaloyl chloride reaction4+Fluorescent probe SnP1.The probe is in Sn4+Show preferable selectivity in the system coexisted with other metal ions, sensitivity is high, response is fast, the features such as invertible operation, can be very good to be applied to Sn in environment4+Detection.

Description

A kind of Sn based on double rhodamines4+Fluorescent probe molecule and preparation method and application
Technical field
The present invention relates to a kind of tin ion (Sn4+) detection agent, and in particular to a kind of Sn based on double rhodamines4+Fluorescence is visited The preparation method of pin.
Background technology
Stannum is widely present in air, soil and water at present, is one of common heavy metal in industry.The industrial revolution with Come, increasing inorganic tin and organotin are introduced in environment.Stannum is trace element needed by human, in adrenal gland, liver, In the organs such as brain, spleen and thyroid, content is most.The shortage of stannum may result in undergrowth and hearing disability, and have some to demonstrate,prove According to showing that stannum take part in somatomedin and prophylaxis of cancer.At the same time, as stannum is widely used in the fields such as agricultural, industry, Stannum also becomes one of common heavy metal contaminants in environment.The excessive stannum of absorption of human body also can cause important shadow to health Ring.The symptom of tin poisoning is limited to gastrointestinal reaction such as nausea, stomachache, vomiting etc. mostly.Therefore, studying one kind being capable of quick detection Sn4+Method tool be of great significance.
Fluorescent probe has the advantages that selectivity is good, sensitivity is high, easy to operate quick, few to detectable substance damage wide The general metal cation being applied in detection environmental and biological materials system, anion, the biological aspect such as active small molecular in vivo.Fluorescence The development and utilization research of probe molecule is the crossing domain of the science such as chemistry and biology, medical science, agricultural.Fluorescent probe technique is The on a molecular scale analysis method studied by object of study.Fluorescent probe has been widely used in environment and life at present The detection of the material such as heavy metal, bioactive small molecule in object.
Dye stuff of rhodamine kinds has high larger molar absorption coefficient, fluorescence quantum yield, preferable optical stability, ripple Long wide ranges and the advantages of to pH stable wide ranges, have been widely used in the design and synthesis of fluorescent probe.In recent years The metal cation that comes during rhodamine derivant is used to be designed to fluorescent probe to detect organism or environment or Anion.The mechanism of rhodamine fluorescence probe identification metal ion is as shown in the figure.The Rhodamine Derivatives of cyclization do not have in itself There are color and fluorescence, but beat its intramolecular lactams volution when corresponding metal cation or anion is added Open, solution can be changed into pink from colourless, while discharging stronger fluorescence.
The content of the invention
It is an object of the invention to provide a kind of Sn based on double rhodamines4+The preparation method of fluorescent probe.
A kind of Sn based on double rhodamines proposed by the present invention4+The preparation method of fluorescent probe, first by sieve of commercialization Red bright B carries out condensation acylation reaction with ethanolamine, obtains a kind of rhodamine B-ethanolamine derivant；Rhodamine B-the ethanolamine spreads out The biological acyl chloride reaction that carries out with m-phthaloyl chloride obtains a kind of compound containing double rhodamine Bs, the compound methanol- Sn can be used as in aqueous solution4+High selectivity fluorescent probe.
A kind of Sn based on double rhodamines proposed by the present invention4+The preparation method of fluorescent probe, its concrete synthetic route is such as Shown in lower：
(1) rhodamine B and ethanolamine are stirred at reflux to fully reaction in ethanol solution, question response cools down anti-completely afterwards Answer system to room temperature, removal of solvent under reduced pressure, dissolved with ethyl acetate again, washed with pure water and saturated nacl aqueous solution, it is organic Anhydrous sodium sulfate drying is mutually used, is filtered, removal of solvent under reduced pressure, the isolated intermediate product RhB-OH of silica gel column chromatography.
(2) intermediate RhB-OH is mixed in dichloromethane solution with triethylamine, under condition of ice bath, is added dropwise to isophthalic two The dichloromethane solution of formyl chloride, should be room temperature reaction after completion of dropping, and after reaction completely, saturated nacl aqueous solution washing has Machine mutually uses anhydrous sodium sulfate drying, filters, removal of solvent under reduced pressure, with ethyl acetate and petroleum ether as detergent, Jing silicagel columns Chromatography obtains product SnP1.
In the step (1), rhodamine B is 1 with the ratio of the amount of the material of ethanolamine:4, the temperature that is heated to reflux is 80-90 DEG C, the response time is 8-15 hours.
In the step (1), the detached eluent of silicagel column is CH2Cl2And CH3OH, the CH2Cl2With CH3The volume of OH Than for 10-18:1, yield is 60-85%.
In the step (2), compound R hB-OH is 2-4 equivalents, and m-phthaloyl chloride is 1 equivalent, and triethylamine ought for 2-5 Amount, room temperature reaction time are 6-10h.
In the step (2), the detached eluent of silicagel column is CH2Cl2And CH3OH, the CH2Cl2With CH3The volume of OH Than for 10-20:1, yield is 60-75%.
Sn based on double rhodamines4+Fluorescent probe molecule is in detection Sn4+In application.
Description of the drawings
Fig. 1 is the fluorescent probe SnP1 hydrogen nuclear magnetic resonance spectrograms of the present invention；
Fig. 2 is the fluorescent probe SnP1 carbon-13 nmr spectra figures of the present invention；
Fig. 3 is the fluorescent probe SnP1 high resolution mass spectrum figures of the present invention；
Fig. 4 be the present invention fluorescent probe SnP1 fluorescence selectivity figures, excitation wavelength 520nm；
Fig. 5 is the fluorescent probe SnP1 identification Sn of the present invention4+Anti-metal Cation Interferences figure, excitation wavelength 520nm, Launch wavelength 577nm；
Fig. 6 is the fluorescent probe SnP1 identification Sn of the present invention4+Anti- anion interference figure, excitation wavelength 520nm, transmitting Wavelength 577nm.
Specific embodiment
The chemical reagent that used during fluorescent probe SnP1 is prepared in the present invention, solvent, metal ion etc. are purchased From Aladdin Reagent Company.Bruke companies DTX-400 type nuclear-magnetisms are adopted in the confirmation and performance test process of fluorescent probe SnP1 Resonance spectrometer, solvent are deuterochloroform, record proton nmr spectra and carbon spectrum by internal standard of TMS.Using the Q- of Thermo companies Exactive HR-MS mass spectrographs record high resolution mass spectrum data.Record glimmering using HIT's F-7000 fluorescence spectrophotometer Light spectrum.
The structure of the final product SnP1 of present invention synthesis obtains proton nmr spectra, carbon spectrum and high resolution mass spectrum really Card.
1st, the preparation of intermediate RhB-OH：
In the single necked round bottom flask of 100mL, hydrochlorate (1.00g, 2.08mmol), the ethanolamine of rhodamine B are added Reactant liquor is cooled to room temperature by (0.54mL, 8.32mmol) and 50mL ethanol, back flow reaction completely rear (10h), and decompression is removed The solid obtained after solvent is dissolved in the ethyl acetate solution of 30mL, with water (30mL × 2) and saturated nacl aqueous solution (30mL × 2) wash, organic faciess anhydrous sodium sulfate drying, filter, (eluent is CH to column chromatography for separation after removal of solvent under reduced pressure2Cl2:CH3OH =10:1, volume ratio) intermediate product RhB-OH is obtained, yield is 75%.
2nd, 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), be added dropwise under condition of ice bath m-phthaloyl chloride (0.2g, Anhydrous methylene chloride solution (15mL) 1mmol), should be room temperature reaction after completion of dropping, after reaction (about 8h) completely, saturation chlorine Change sodium solution (30mL × 2) washing, organic faciess anhydrous sodium sulfate drying is filtered, removal of solvent under reduced pressure, Jing silica gel column chromatographies point From (eluent is CH2Cl2:CH3OH=15:1, volume ratio) product SnP1 is obtained, yield is 69%.
Nuclear magnetic resonance hydrogen spectruming determining：1H NMR(CDCl3, 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 =8 Hz, 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 is determined：13C NMR(CDCl3,100MHz)δ168.53,165.1,153.9,153.1,148.8, 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 is determined：HR-ESI-MS calcd for C68H73N6O8 +：1101.5484,found 1101.5344。
3rd, the application examples of probe SnP1
The preparation of solution：
Metal inorganic salt：Plumbi nitrass, silver nitrate, cadmium nitrate, other are chloride (K+,Na+,Ca2+,Mg2+,Ba2+,Zn2 +,Fe2+,Fe3+,Mn2+,Cu2+,Co2+,Ni2+,Hg2+) and producer is Aladdin Reagent Company or Tianjin Ke Miou reagents are public Department.Precise respective metal salt, prepares the solution for standby of 10mM in being dissolved in high purity water.
The probe solution of 1mM is prepared：Precise correspondent probe (SnP1), SnP1 prepare 1mM in being dissolved in methanol solution Solution for standby.
Fluorescence selectivity is tested：
Its fluorescence selectivity is tested using fluorescence spectrophotometer.As shown in Figure 4, single probe SnP1 (10 μ M) in CH3OH-H2There is faint fluorescent emission intensity, as addition Sn in O (99/1, v/v) solution4+(10 equivalent) its fluorescence afterwards Emissive porwer is remarkably reinforced, but when adding other metal ions (100 μM), only adds Fe3+, Sn2+, Cr3+Solution system Fluorescence intensity has certain enhancing, but response intensity, than relatively low, remaining metal ion system fluorescence intensity does not have significant change.More than Test result indicate that, the probe has preferable single-minded selectivity to mercury ion.
Fluorescence interference is tested：
In order to test probe molecule to Sn4+The capacity of resisting disturbance of detection, tests its gold in fluorescence emission spectrum respectively Category Cation Interferences and anion interference.As shown in Figure 5, in SnP1 (10 μM) in CH3OH-H2O (99/1, v/v) solution In be separately added into the various metal cations (100 μM) of test and test its fluorescent emission intensity (577nm), then again to containing each 100 μM of Sn is added in the solution of metal ion species4+Solution, from accompanying drawing 5, adds hydrargyrum in the presence of other metal cations Ion is essentially identical with fluorescence intensity (577nm) resulting when being individually added into mercury ion, and the result shows probe SnP1 to Sn4+ Detection with stronger anti-metal Cation Interferences ability.In a similar way, which is tested to Common Anions (Cl-, Br-,F-, I-, CO3 2-,NO3 -,PO4 3-,SO4 2-) capacity of resisting disturbance, as shown in Figure 6, probe SnP1 is to Sn4+Detection have Stronger anti-anion interference performance.

Claims (7)

1. a kind of Sn based on double rhodamines4+Fluorescent probe molecule, it is characterised in that the following institute of the fluorescent probe structural formula Show：
2. the Sn based on double rhodamines as described in right 1 is required4+The preparation method of fluorescent probe molecule, it is characterised in that：It The step of it is as follows：
(1) rhodamine B and ethanolamine are stirred in ethanol solution, is heated to reflux to fully reaction, question response is cooled down completely afterwards Reaction system is dissolved with ethyl acetate, is washed with pure water and saturated nacl aqueous solution, organic faciess to room temperature, removal of solvent under reduced pressure With anhydrous sodium sulfate drying, filter, removal of solvent under reduced pressure, the isolated intermediate product RhB-OH of silica gel column chromatography；
(2) intermediate product RhB-OH is mixed in dichloromethane solution with triethylamine, under condition of ice bath, is added dropwise to isophthalic diformazan The dichloromethane solution of acyl chlorides, is changed to room temperature reaction after completion of dropping, after reaction completely, saturated nacl aqueous solution washing is organic Anhydrous sodium sulfate drying is mutually used, is filtered, removal of solvent under reduced pressure, with dichloromethane and methanol as detergent, Jing silica gel column chromatographies The isolated Sn containing double rhodamines4+Fluorescent probe molecule SnP1.
3. the Sn based on double rhodamines as claimed in claim 24+The preparation method of fluorescent probe molecule, it is characterised in that：Institute State in step (1), rhodamine B is 1 with the ratio of the amount of the material of ethanolamine:4, described to be heated to reflux temperature for 80-90 DEG C, reaction Time is 8-15 hours.
4. the Sn based on double rhodamines as claimed in claim 24+The preparation method of fluorescent probe molecule, it is characterised in that：Institute State in step (1), the detached eluent of silicagel column is CH2Cl2And CH3OH, the CH2Cl2With CH3The volume ratio of OH is 10-18: 1, yield is 60-85%.
5. the Sn based on double rhodamines as claimed in claim 24+The preparation method of fluorescent probe molecule, it is characterised in that：Institute State in step (2), compound R hB-OH is 2-4 equivalents, and m-phthaloyl chloride is 1 equivalent, and triethylamine is 2-5 equivalents, and room temperature is anti- It is 6-10h between seasonable.
6. the Sn based on double rhodamines as claimed in claim 24+The preparation method of fluorescent probe molecule, it is characterised in that：Institute State in step (2), the detached eluent of silicagel column is CH2Cl2And CH3OH, the CH2Cl2With CH3The volume ratio of OH is 10-20: 1, yield is 60-75%.
7. the Sn based on double rhodamines as claimed in claim 14+Fluorescent probe molecule is in detection Sn4+In application.
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