CN107129503B - A kind of detection Cr quick in aqueous solution3+The preparation method and applications of the enhanced probe of ion fluorescence - Google Patents

A kind of detection Cr quick in aqueous solution3+The preparation method and applications of the enhanced probe of ion fluorescence Download PDF

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CN107129503B
CN107129503B CN201710314435.7A CN201710314435A CN107129503B CN 107129503 B CN107129503 B CN 107129503B CN 201710314435 A CN201710314435 A CN 201710314435A CN 107129503 B CN107129503 B CN 107129503B
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CN107129503A (en
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侯淑华
张思琦
任冬梅
钟克利
刘玉静
赵岩
汤立军
边延江
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Bohai University
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Abstract

A kind of detection Cr quick in aqueous solution3+The preparation method and applications of the enhanced probe of ion fluorescence, take compound 1L-Histidine, potassium carbonate are dissolved in methanol, under nitrogen protection, are stirred at reflux reaction, are cooled to room temperature, and solvent is fallen in vacuum distillation, are separated using silica gel column chromatography, are obtained fluorescence probe LFluorescence enhancement type probe L is that rhodamine B fluorescence probe being capable of Selective recognition Cr3+The solvent of ion is aqueous solution.Advantage is: to Cr3+Identification have excellent selectivity, high specificity, fluorescence probe L and Cr3+After effect, fluorescence enhancement is shown as, is realized to Cr3+Fluorescence enhancement identification, detection sensitivity is high, does not change substantially with other common metal ions effect fluorescence signal, strong antijamming capability can be used for Cr3+Identification.

Description

A kind of detection Cr quick in aqueous solution3+The preparation side of the enhanced probe of ion fluorescence Method and its application
Technical field
The invention belongs to trivalent chromic ion detection fields, in particular to a kind of that Cr is quickly detected in pure water solution3+Ion The preparation method and applications of fluorescence enhancement type probe.
Background technique
Trivalent chromic ion is one of the essential trace elements of the human body, it has important influence to the health of human body.Cr3+From The content of son in human body can be reduced with advancing age.When lacking trivalent chromium in human body, just it is easy to show sugar Metabolism disorder, induced Diabetic, coronary sclerosis lead to cardiovascular disease, serious to may result in cataract, blindness, uremic The complication such as disease.However, Cr3+The Excess free enthalpy of ion but will cause poisoning, cause the wide of liver, kidney, blood and nervous system General lesion, leads to death.Currently, can Xiang Huan in the preparation process such as metal plating, commercial pigments and tanning, rubber and ceramic raw material A large amount of chromium ions are discharged in border such as water, chromium ion enters in water body, passes through food chain in vivo by entering fish, livestock etc. Into into the human body, high risks are generated to human health.Therefore, exploitation is quickly, the method gesture of cheap detection chromium ion is must Row.
Fluorescence probe has good, the simple and quick, high sensitivity of selectivity, and the characteristics of do not need by expensive instrument, It is widely used in the detection of each metal ion species.Cr3+Has the characteristics that paramagnetism, so that many fluorescence probes and Cr3+Effect Afterwards, it is usually expressed as fluorescent quenching, has seriously affected the sensitivity of detection.Also, most of the fluorescence probe of preparation is that having It is tested in solvent, " one kind identifies Fe based on rhodamine B as disclosed in CN1056236493+、Al3+And Cr3+Ion is multi-functional Fluorescence probe and its preparation method and application ", which can not identify in pure water, and Cr3+It is present in water, It will affect accuracy, the sensitivity of detection in organic solvent, and be not suitable for testing in life entity, answered to limit it Use range.
Summary of the invention
The technical problem to be solved in the present invention is to provide one kind have excellent sensitivity, strong anti-interference ability, can be in pure water Cr is quickly detected in solution3+The preparation method and applications of the enhanced probe of ion fluorescence.
The technical scheme is that
A kind of detection Cr quick in aqueous solution3+The preparation method of the enhanced probe of ion fluorescence, reaction equation are as follows:
It comprises the concrete steps that:
Take compound 1L-Histidine, potassium carbonate are dissolved in methanol according to molar ratio 1:1.5:2, Under nitrogen protection, it is stirred at reflux reaction 20h；After the reaction was completed, it is cooled to room temperature, solvent is fallen in vacuum distillation, using silicagel column Chromatography obtains fluorescence probe L
A kind of detection Cr quick in aqueous solution3+The application of the enhanced probe of ion fluorescence.
A kind of detection Cr quick in aqueous solution3+The application of the enhanced probe of ion fluorescence, the rhodamine B fluorescence are visited Needle being capable of Selective recognition Cr3+The solvent of ion is aqueous solution.
A kind of detection Cr quick in aqueous solution3+The application of the enhanced probe of ion fluorescence is added glimmering in detection water sample The phosphate buffer of light probe L measures its fluorescent emission intensity under the excitation wavelength of λ=530nm, the fluorescence at 588nm Intensity significantly increases, and contains Cr in the detection water sample3+Ion.
A kind of detection Cr quick in aqueous solution3+The application of the enhanced probe of ion fluorescence is added glimmering in detection water sample The phosphate buffer of light probe L issues orange light, contains Cr in the detection water sample under λ=365nm irradiation3+Ion.
Beneficial effects of the present invention:
1) fluorescence probe L is to Cr3+Identification have excellent selectivity, high specificity, fluorescence probe L and Cr3+Effect Afterwards, fluorescence enhancement is shown as, is realized to Cr3+Fluorescence enhancement identification, detection sensitivity is high, such as with other common metal ions Zn2+、Pb2+、Cu2+、Fe2+、Cd2+、 Mn2+、Co2+、Ni+、Cr3+、Ag+、Na+、Ba2+、Sr2+、Hg2+、Mg2+Act on fluorescence signal base This does not change, and strong antijamming capability can be used for Cr3+Identification.
2) fluorescence probe L has water soluble nature, to Cr3+Identification can carry out in aqueous solution, organic solvent-free Participation, increase the accuracy and application range of detection.
Detailed description of the invention
Fig. 1 is fluorescence probe L of the present invention1H NMR spectra；
Fig. 2 is fluorescence probe L of the present invention13C NMR spectra；
Fig. 3 is the high resolution mass spectrum spectrogram of fluorescence probe L of the present invention；
Fig. 4 is the fluorescence spectrum that different metal ions are added in fluorescence probe L of the present invention in aqueous solution；
Fig. 5 is fluorescence probe L of the present invention Cr in aqueous solution3+Fluorescence titration spectrum；
Fig. 6 is fluorescence probe L of the present invention in Cr3+And the fluorescent emission intensity variation diagram in the presence of other metal ions.
Specific embodiment
The present invention can be further illustrated by the following examples, but be not limited solely to embodiment.
Embodiment 1
Synthesize compound 1Its reaction equation is as follows:
It takes rhodamine B (444mg, 1mmol) to be dissolved in dry methylene chloride, benzotriazole-N, N, N' is added, N'- tetramethylurea hexafluorophosphoric acid ester (HBTU, 568mg, 1.5mmol), 2- bromine ethylamine hydrobromide (306mg, 1.5mmol) and Triethylamine (152mg, 1.5mmol), at room temperature reaction overnight；After reaction, methylene chloride, gains are fallen in vacuum distillation Using column chromatography for separation (silica gel, VEthyl acetate:VPetroleum ether=1:5), obtain 410mg white solid, yield 75%.
Embodiment 2
Fluorescence probe L is synthesized, reaction equation is as follows:
It comprises the concrete steps that:
L-Histidine (116mg, 0.75mmol) is dissolved in dry methanol (50mL), potassium carbonate is added into solution 10min is stirred at room temperature in (139mg, 1mmol), and compound 1 is then added(273mg, 0.5mmol) compound, back flow reaction 20h；It is cooled to room temperature after the reaction was completed, solvent is removed in vacuum distillation, and gains use column Chromatography (silica gel, VAmmonium hydroxide:VIsopropanol=1:15), obtain 143mg white solid rhodamine B fluorescence probe LYield is 46%.
The master data of the rhodamine fluorescence probe:
1H NMR(400MHz,CDCl3) δ 8.08 (d, J=7.7Hz, 1H), 7.56 (s, 1H), 7.52 (d, J=7.4Hz, 1H), 7.47 (t, J=7.5Hz, 1H), 7.14 (d, J=7.5Hz, 1H), 6.97 (s, 1H), 6.39 (m, 4H), 6.24 (m, 1H), 5.18 (dd, J=7.5,5.1Hz, 1H), 4.11 (tt, J=7.5,6.1Hz, 1H), 3.78 (s, 1H), 3.66 (d, J= 8.1Hz, 1H), 3.44-3.17 (m, 12H), 1.25-1.14 (m, 12H) (such as Fig. 1).
13C NMR(100MHz,CDCl3)δ173.2,159.9,154.4,153.2,149.5,149.3,135.0,134.1, 129.1,128.5,126.1,125.3, 124.9,108.5,102.1,102.0,97.6,72.1,64.5,60.3,46.4, 44.32,25.4,12.5 (such as Fig. 2).
HRMS(ESI+)calcd for C36H43N6O4[M+H]+: 623.3340, found:m/z 623.3305 (such as Fig. 3).
The fluorescence spectrometry of fluorescence probe L:
The fluorescence spectrometry solution of fluorescence probe L is prepared, and using deionized water as solvent, prepares 1.0 × 10-3Mol/L's Then the solution of fluorescence probe L is diluted to 1.0 × 10 with phosphate buffer solution (10mmol/L, pH 7.2) again-5mol/L；It takes 2mL concentration is 1.0 × 10-5The fluorescence probe L solution of mol/L, being then respectively adding 80 μ L concentration is 1.0 × 10-3Mol/L's Various ion (Zn2+、Pb2+、Cu2+、Fe2+、Cd2+、Mn2+、Co2+、Ni+、 Cr3+、Ag+、Na+、Ba2+、Sr2+、Hg2+、Mg2+) molten Liquid shakes up, after its fluorescence emission spectrum (such as Fig. 4) is measured under the excitation wavelength of λ=530nm, as a result, it has been found that fluorescence probe L is glimmering Luminous intensity is very weak；Cr is added3+Afterwards, fluorescence probe L fluorescence intensity at 588nm significantly increases (λ=530nm), in λ=365nm Irradiation is lower to issue orange light, can be identified by naked eyes, and other ions do not find similar variation.
The fluorescence spectroscopic titration of fluorescence probe L is tested and the measurement of detection limit:
Taking 2mL concentration is 1.0 × 10-5The phosphate buffer solution (10mmol/L, pH 7.2) of the fluorescence probe L of mol/L, adds The metal ion for entering various concentration can be found, with Cr3+The increase of concentration, fluorescence probe L fluorescence intensity at 588nm gradually increase By force, work as Cr3+Concentration reaches peak when being 90 times (Fig. 5) of fluorescence probe L concentration, illustrates to reach highest saturation multiple.It is logical Good linear relationship is presented in the relation curve for crossing ion concentration and fluorescence intensity.Wherein fluorescence probe L is to Cr3+Detection be limited to 1.1×10-6Mol/L, R=0.9968.
Fluorescence probe L to Cr3+The selectivity and anti-interference of ion identification:
Taking 2mL concentration is 1.0 × 10-5The phosphate buffer solution (10mmol/L, pH 7.2) of the fluorescence probe L of mol/L, so After be separately added into 80 μ L concentration be 1.0 × 10-3The ion Cr of mol/L3+Solution shakes up, after under the excitation wavelength of λ=530nm Its fluorescence emission spectrum is measured, other metal ions are added as the result is shown such as: Zn2+、Pb2+、Cu2+、Fe2+、Cd2+、Mn2+、Co2+、 Ni+、Cr3+、Ag+、Na+、Ba2+、Sr2+、Hg2+、K+、Mg2+, to its fluorescent emission and visible absorbance intensity effect very little, this is with regard to table Fluorescence probe L is illustrated to Al3+Identify selectivity with higher and preferable anti-interference ability (Fig. 6).
The above is only specific embodiments of the present invention, are not intended to restrict the invention, for those skilled in the art For member, the invention may be variously modified and varied.All within the spirits and principles of the present invention, it is made it is any modification, Equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.

Claims (3)

1. a kind of fluorescence enhancement type probe quickly detects Cr in aqueous solution3+The method of ion, it is characterized in that: the fluorescence enhancement type The structural formula of probe L are as follows:
；
Its specific synthesis step is:
Take compound 1, L-Histidine, potassium carbonate is dissolved according to molar ratio 1:1.5:2 In methanol, under nitrogen protection, it is stirred at reflux 20 h of reaction；After the reaction was completed, it is cooled to room temperature, solvent is fallen in vacuum distillation, adopts It is separated with silica gel column chromatography, obtains fluorescence enhancement type probe L；
Fluorescence enhancement type probe L being capable of Selective recognition Cr in aqueous solution3+Ion, solvent used in identification process are water Solution.
2. detection Cr quick in aqueous solution according to claim 13+The preparation method system of the enhanced probe of ion fluorescence Standby fluorescence enhancement type probe quickly detects Cr in aqueous solution3+The application of ion, it is characterized in that: being added in detection water sample The phosphate buffer of fluorescence enhancement type probe L, measures its fluorescent emission intensity under the excitation wavelength of the nm of λ=530, Fluorescence intensity significantly increases at 588nm, contains Cr in the detection water sample3+Ion.
3. detection Cr quick in aqueous solution according to claim 13+The preparation method system of the enhanced probe of ion fluorescence Standby fluorescence enhancement type probe quickly detects Cr in aqueous solution3+The application of ion, it is characterized in that: being added in detection water sample The phosphate buffer of fluorescence enhancement type probe L issues orange light, contains Cr in the detection water sample under the nm of λ=365 irradiation3+ Ion.
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CN108640948A (en) * 2018-04-26 2018-10-12 福建师范大学泉港石化研究院 A kind of detection Cr3+Rhodamine base fluorescent probe and preparation method thereof
CN109134529A (en) * 2018-09-11 2019-01-04 佛山市元通胶粘实业有限公司 A kind of synthetic method of bis- (levulinic ketone group) tin of di-n-butyl
CN112358486A (en) * 2021-01-07 2021-02-12 黄月金 Detection of Pb in acidic aqueous solutions2+Fluorescent probe for ions and preparation method thereof

Citations (4)

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CN104263356A (en) * 2014-09-29 2015-01-07 辽宁大学 Rhodamine pH fluorescent probe containing methionine structure and application of rhodamine pH fluorescent probe
CN104447774A (en) * 2014-11-12 2015-03-25 南京理工大学 Rhodamine B-based fluorescence sensor and preparation
CN104650105A (en) * 2015-02-12 2015-05-27 西安交通大学 Rhodamine B derivative containing 8-aminoquinoline group, preparation method, application and method for carrying out fluorescence analysis on Cr<3+> and Cu<2+>
CN105693736A (en) * 2016-03-26 2016-06-22 辽宁大学 Glycine structure containing Rhodamine photo-control fluorescent switch probe and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104263356A (en) * 2014-09-29 2015-01-07 辽宁大学 Rhodamine pH fluorescent probe containing methionine structure and application of rhodamine pH fluorescent probe
CN104447774A (en) * 2014-11-12 2015-03-25 南京理工大学 Rhodamine B-based fluorescence sensor and preparation
CN104650105A (en) * 2015-02-12 2015-05-27 西安交通大学 Rhodamine B derivative containing 8-aminoquinoline group, preparation method, application and method for carrying out fluorescence analysis on Cr<3+> and Cu<2+>
CN105693736A (en) * 2016-03-26 2016-06-22 辽宁大学 Glycine structure containing Rhodamine photo-control fluorescent switch probe and application thereof

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