CN103484102A - Rhodamine difunctional fluorescence probe and application thereof - Google Patents
Rhodamine difunctional fluorescence probe and application thereof Download PDFInfo
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- CN103484102A CN103484102A CN201310327093.4A CN201310327093A CN103484102A CN 103484102 A CN103484102 A CN 103484102A CN 201310327093 A CN201310327093 A CN 201310327093A CN 103484102 A CN103484102 A CN 103484102A
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Abstract
The invention provides a rhodamine difunctional fluorescence probe and application thereof. The specific structural formula of the probe is described in the specification. The fluorescence probe recognizes Cu<2+> and Hg<2+> in different solvents, respectively. The probe has the advantages of excellent selectivity in recognition of Cu<2+> and Hg<2+>, almost unchanged fluorescence signals during reaction with other common metal ions, strong anti-jamming capability, good sensing properties, a low detection limit and high detection sensitivity. Selectivity is controlled by regulating and controlling the service environment of the fluorescence probe, so multi-functionalization of the fluorescence ion probe is realized; i.e., selectivity on the two different metal ions consisting of Cu<2+> and Hg<2+> can be conveniently realized through changing of an applied solvent system, so both detection cost and detection time are saved.
Description
Technical field
The present invention relates to a kind of rhodamine Multifunction fluorescent probe and application thereof.
Background technology
Cupric ion is the transition metal ion of human body relaying iron and zine ion the 3rd enrichment afterwards.Copper is essential a kind of trace element in animal and plant body, and the effect of nearly twenties kinds of enzymes need to have the participation of cupric ion, as Terminal oxidase, and superoxide dismutase, tyrosine oxidase, dopamine β-hydroxylase, lysyloxidase etc., when but in body, content of copper ion is too high, the cupric ion of high density can cause cell impaired and downright bad, causes organ function injury.Mercury ion has serious toxic action to HUMAN HEALTH and environment, reason be mercury ion persistence, easily the migration and the height bioconcentration characteristics.In addition, mercury and mercury salt are used extensively in industry, and in environment, the detection of mercury just becomes particularly important.Therefore, develop a kind of cost low, the response fast can be for the Cu of physical environment and living things system
2+and Hg
2+detection method particularly important.
At present, the fluorescent ion probe technology is an effective way of metal ion detection, the synthetic modification that mainly lays particular emphasis on structure of the design of fluorescent ion probe, especially by the change of ion receptor structural unit, realize the regulation and control of ion selectivity, but the selectivity of this expection often is difficult to control, and the subtle change of some ion receptor structure also can affect greatly selectivity.Therefore, the metal-ion fluorescent recognition methods of employing is all to design corresponding fluorescent probe molecule for a certain specific metal ion, detects ion single.And cupric ion and mercury ion have the paramagnetism characteristics, after making a lot of fluorescent probes and cupric ion or mercury ion effect, be usually expressed as fluorescent quenching, had a strong impact on the sensitivity detected.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind ofly to be had good sensitivity, stronger immunity from interference, can in different solvents, identify respectively Cu
2+and Hg
2+rhodamine Multifunction fluorescent probe and application thereof.
Technical solution of the present invention is:
A kind of rhodamine Multifunction fluorescent probe, this fluorescent probe is the derivative of sulfo-rhodamine B hydrazides, the concrete structure formula is as follows:
A kind of application of rhodamine Multifunction fluorescent probe, described rhodamine Multifunction fluorescent probe is identified respectively Cu in different solvents
2+and Hg
2+.
A kind of application of rhodamine Multifunction fluorescent probe, described rhodamine Multifunction fluorescent probe identification Cu
2+solvent be H
2o and CH
3the H that the CN volume ratio is 1:1
2o-CH
3cN solution.
A kind of application of rhodamine Multifunction fluorescent probe, described rhodamine Multifunction fluorescent probe identification Hg
2+solvent be H
2the H that O and DMSO volume ratio are 95:5
2o-DMSO solution.
Beneficial effect of the present invention:
(1) this fluorescent probe has the rhodamine fluorophore, spirolactams and Cu
2+or Hg
2+the effect open loop after, by the closed loop state become hyperfluorescenceZeng Yongminggaoyingguang without fluorescence, realized Cu
2+and Hg
2+fluorescence strengthen identification, detection sensitivity is high.
(2) this fluorescent probe is to Cu
2+and Hg
2+identification good selectivity is arranged, with other common metal ion effect fluorescent signal, substantially do not have to change, immunity from interference is strong, has sensing character preferably, detectability is low.
(3) control selectivity by the environment for use of regulation and control fluorescent probe, make the fluorescent probe ion realize multifunction,, only by changing applied solvent system, just can realize Cu easily
2+and Hg
2+the selectivity of two kinds of different metal ions, both can save testing cost, saved detection time again.
The accompanying drawing explanation
Fig. 1 is fluorescent probe of the present invention
1h NMR spectrogram;
Fig. 2 is fluorescent probe of the present invention
13c NMR spectrogram;
Fig. 3 is the mass spectrogram of fluorescent probe of the present invention;
Fig. 4 is the fluorescence emission spectrogram of fluorescent probe of the present invention to the identification of cupric ion selectivity;
Fig. 5 is fluorescent probe of the present invention fluorescence emission spectrum variation diagram under the different concns cupric ion exists;
Fig. 6 is the fluorescent emission intensity variation diagram of fluorescent probe of the present invention under cupric ion and the existence of other metal ion;
Fig. 7 is the detectability scaling system of fluorescent probe of the present invention to cupric ion;
Fig. 8 is the fluorescence emission spectrogram of fluorescent probe of the present invention to the identification of mercury ion selectivity;
Fig. 9 is fluorescent probe of the present invention fluorescence emission spectrum variation diagram under the different concns mercury ion exists;
Figure 10 is the fluorescent emission intensity variation diagram of fluorescent probe of the present invention under mercury ion and the existence of other metal ion;
Figure 11 is the detectability scaling system of fluorescent probe of the present invention to mercury ion.
Embodiment
(1) reaction formula of the bright class Multifunction fluorescent of synthesizing rhodamine probe:
(2) concrete steps of the bright class Multifunction fluorescent of synthesizing rhodamine probe:
Take intermediate 2-amino-3' of 473mg, 6'-bis-(diethylamino)-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe oxine of)-thioketones (compound 2) and 175mg-2-formaldehyde (compound 3), be dissolved in the 30mL absolute ethanol stirring heating back flow reaction 10h.Vacuum rotary steam is except desolventizing, obtain faint yellow solid, then separate (elutriant is petroleum ether-ethyl acetate, volume ratio 10:1) through silica gel column chromatography and obtain target fluorescent probe 3', 6'-bis-(diethylamino)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones (compound 1), yield is 62%.
Fluorescent probe 3' in embodiment 1,6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe master data of)-thioketones:
1h NMR (400 MHz, DMSO-
d 6)
δ(8.76 s, 1H), 8.23-8.18 (m, 3H), 8.08 (d,
j=8.8 Hz, 1H), 7.48-7.43 (m, 3H), 7.30 (d,
j=8.0 Hz, 1H), 7.25 (s, 1H), 7.19-7.16 (m, 2H), 6.79 (d,
j=8.4 Hz, 2H), 6.33 – 6.29 (m, 4H), 3.32 (dd,
j=6.8 Hz, 8H), 1.15 (t,
j=6.8 Hz, 12H). (as Fig. 1).
13c NMR (100 MHz, DMSO-
d 6).
δ174.26,158.55,155.48,152.39,151.89,151.67,148.26,137.85,136.12,135.12,132.66,130.08,128.80,128.73,127.99,127.12,122.62,119.62,117.84,110.34,110.01,108.23,97.42,44.37,12.62. (as Fig. 2).
The calculated value C of high resolution mass spectrum (electron spray(ES), holotype)
38h
38n
5o
2s [M+H]
+, 628.2746; Measured value 628.2741.(is as Fig. 3).
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones is to Cu
2+selectivity detect:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-CH
3cN(1:1, v/v, HEPES 10mmol/L, pH 7.4) solution, add respectively the metal ion (Ni of 40 μ mol/L
2+, Hg
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Ag
+, Fe
2+, Fe
3+, Cu
2+, Zn
2+, Cd
2+), the fluorescence emission spectrum that detects solution after 1.5h changes, and result is as shown in Figure 4.As shown in Figure 4, fluorescent probe is from the 632nm place, almost there is no emission peak; When adding Cu
2+after ion, strong emission peak appears in fluorescent probe solution at the 632nm place, when adding Hg
2+after ion, weak emission peak appears in fluorescent probe solution at the 632nm place; Yet other metal ion, as Ni
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Zn
2+, Cd
2+, Ag
+, Fe
2+, Fe
3+after, fluorescent probe solution at the emission peak at 632nm place without obvious enhancing; Experimental result shows, only adds Cu
2+, just can cause that the remarkable fluorescence of fluorescent probe solution strengthens, this fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) and methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones is at H
2o-CH
3cN(1:1, v/v, HEPES 10mmol/L, pH 7.4) in solution to Cu
2+there is good selectivity.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones to Cu
2+fluorometric titration experiment:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-CH
3cN(1:1, v/v, HEPES 10mmol/L, pH=7.4) solution, the Cu progressively added
2+concentration, after 1.5h the test each sample fluorescence spectrum, result is as shown in Figure 5.As seen from Figure 5, along with Cu
2+the increase gradually of concentration, probe solution also increases gradually in the fluorescence intensity at 632nm place, works as Cu
2+concentration while increasing to 40 μ mol/L, titration reaches capacity, emissive porwer no longer increases; This also illustrates that this fluorescent probe is to Cu
2+there is sensing character preferably.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones to Cu
2+the competitive assay of identification:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-CH
3cN(1:1, v/v, HEPES 10mmol/L, pH=7.4) solution, add respectively other metal ion (Ni of 40 μ mol/L
2+, Hg
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Ag
+, Fe
2+, Fe
3+, Cd
2+, and Zn
2+, the fluorescence spectrum of each solution of test after 1.5h; Then to the Cu that adds respectively 40 μ mol/L in the above solution that each contains metal ion
2+, after placement 1.5h, test respectively again the fluorescence spectrum of each solution.Acquired results as shown in Figure 6.As seen from Figure 6, other metal ion coexisted is to Cu
2+fluorescence identification significantly do not disturb.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe calculating of)-thioketones to the cupric ion detectability:
Detectability calculates according to the fluorescence spectrum titration data.With normalized fluorescence intensity (
i-
i min)/(
i max-
i min) be ordinate zou, Cu
2+the logarithm Log[Cu of concentration
2+] be the X-coordinate mapping, as shown in Figure 7.Cupric ion be 3.5 μ mol/L in the concentration range of 20 μ mol/L, linear relationship better (
r=0.99799), straight-line equation is y=6.71453+1.20691x.The intersection point of this straight line and transverse axis is the detection limit value, detects and is limited to 2.73 * 10 as calculated
-6m.In formula
ifor the fluorescence intensity of each sample,
i minfor not adding the fluorescence intensity that cupric ion is probe solution,
i maxit is the fluorescence intensity of sample while adding saturated multiple cupric ion.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones to Hg
2+selectivity experiment:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-DMSO(95:5, v/v, HEPES 10mmol/L, pH=7.4) solution, the fluorescence emission spectrum of this fluorescent probe as shown in Figure 4, adds respectively each metal ion species (Ni of 180 μ mol/L
2+, Hg
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Ag
+, Fe
2+, Fe
3+, Cu
2+, Zn
2+, Cd
2+), the fluorescence emission spectrum that detects solution after 1.5h changes, and result is as shown in Figure 8.As shown in Figure 8, fluorescent probe is from the 629nm place, almost there is no emission peak; When adding Hg
2+after ion, strong emission peak appears in fluorescent probe solution at the 629nm place, when adding Cu
2+after ion, weak emission peak appears in fluorescent probe solution at the 629nm place; Yet other metal ion, as Ni
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Zn
2+, Cd
2+, Ag
+, Fe
2+, Fe
3+after, fluorescent probe solution at the emission peak at 629nm place without obvious enhancing; Experimental result shows, only adds Hg
2+, just can cause that the remarkable fluorescence of fluorescent probe solution strengthens, this fluorescent probe is at H
2o-CH
3cN(1:1, v/v, HEPES 10mmol/L, pH 7.4) in solution to Hg
2+good selectivity is arranged.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones to Hg
2+fluorometric titration experiment:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-DMSO(95:5, v/v, HEPES 10mmol/L, pH=7.4) solution, the Hg progressively added
2+concentration, after 1.5h the test each sample fluorescence spectrum, result is as shown in Figure 9.As seen from Figure 9, along with Hg
2+the increase gradually of concentration, probe solution also increases gradually in the fluorescence intensity at 629nm place, works as Hg
2+concentration while increasing to 180 μ mol/L, titration reaches capacity, emissive porwer no longer increases; This also illustrates that this fluorescent probe is to Hg
2+there is sensing character preferably.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
h)-thioketones to Hg
2+the competitive assay of identification:
5 μ mol/L3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe H of)-thioketones (fluorescent probe)
2o-DMSO(95:5, v/v, HEPES 10mmol/L, pH=7.4) solution, add respectively other metal ion (Ni of 180 μ mol/L
2+, Ba
2+, Mg
2+, K
+, Al
3+, Mn
2+, Pb
2+, Na
+, Sr
2+, Co
2+, Cr
3+, Ag
+, Cu
2+, Fe
2+, Fe
3+, Cd
2+, and Zn
2+, the fluorescence spectrum of each solution of test after 1.5h; Then to the Hg that adds respectively 180 μ mol/L in the above solution that each contains metal ion
2+ion, test respectively the fluorescence spectrum of each solution after placement 1.5h again.Acquired results as shown in figure 10.As seen from Figure 10, except Hg
2+outward, other metal ion all can not cause the remarkable enhancing of fluorescence intensity, and after continuing to add mercury ion, the fluorescence intensity of each sample solution all significantly strengthens, and as can be seen here, other metal ion coexisted is to Hg
2+fluorescence identification significantly do not disturb.
Fluorescent probe 3', 6'-bis-(diethylin)-2-[[(8-hydroxyl-2-quinoline) methylene radical] amino]-spiral shell [1
h-isoindole-1,9'-[9
h] xanthene]-3 (2
hthe calculating of)-thioketones to the mercury ion detecting limit: detectability calculates according to the fluorescence spectrum titration data.With normalized fluorescence intensity (
i-
i min)/(
i max-
i min) be ordinate zou, Hg
2+the logarithm Log[Hg of concentration
2+] be the X-coordinate mapping, as shown in figure 11.Cupric ion be 5 μ mol/L in the concentration range of 41 μ mol/L, linear relationship better (
r=0.99532), straight-line equation is y=0.88706+0.16128x.The intersection point of this straight line and transverse axis is the detection limit value, detects and is limited to 3.16 * 10 as calculated
-6m.In formula
ifor the fluorescence intensity of each sample,
i minfor not adding the fluorescence intensity that mercury ion is probe solution,
i maxit is the fluorescence intensity of sample while adding saturated multiple mercury ion.
Claims (4)
1. a rhodamine Multifunction fluorescent probe, it is characterized in that: the concrete structure formula is as follows:
2. the application of a kind of rhodamine Multifunction fluorescent probe as claimed in claim 1 is characterized in that: described rhodamine Multifunction fluorescent probe is identified respectively Cu in different solvents
2+and Hg
2+.
3. the application of a kind of rhodamine Multifunction fluorescent probe according to claim 2 is characterized in that: described rhodamine Multifunction fluorescent probe identification Cu
2+solvent be H
2o and CH
3the H that the CN volume ratio is 1:1
2o-CH
3cN solution.
4. the application of a kind of rhodamine Multifunction fluorescent probe according to claim 2 is characterized in that: described rhodamine Multifunction fluorescent probe identification Hg
2+solvent be H
2the H that O and DMSO volume ratio are 95:5
2o-DMSO solution.
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Cited By (6)
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| CN103820103A (en) * | 2014-02-20 | 2014-05-28 | 东华大学 | Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof |
| CN105623649A (en) * | 2016-02-01 | 2016-06-01 | 渤海大学 | Rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions |
| CN105646511A (en) * | 2016-03-19 | 2016-06-08 | 云南中烟工业有限责任公司 | Rhodamine 6G-based mercury ion detection fluorescent probe molecule, preparation method and application |
| CN106076295A (en) * | 2016-07-01 | 2016-11-09 | 四川大学 | A kind of can trivalent chromium the preparation method of magnetic nanometer adsorbent that it is quickly removed in fluorescence detection water body |
| CN108219773A (en) * | 2016-12-23 | 2018-06-29 | 泰山医学院 | Pyridine [1,2-a] and benzimidizole derivatives class Hg2+Ratio fluorescent probe and its application |
| CN110498803A (en) * | 2019-09-06 | 2019-11-26 | 山东师范大学 | A kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103820103A (en) * | 2014-02-20 | 2014-05-28 | 东华大学 | Reactive rhodamine fluorescent probe for detecting mercury ions, and preparation method thereof |
| CN105623649A (en) * | 2016-02-01 | 2016-06-01 | 渤海大学 | Rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions |
| CN105646511A (en) * | 2016-03-19 | 2016-06-08 | 云南中烟工业有限责任公司 | Rhodamine 6G-based mercury ion detection fluorescent probe molecule, preparation method and application |
| CN106076295A (en) * | 2016-07-01 | 2016-11-09 | 四川大学 | A kind of can trivalent chromium the preparation method of magnetic nanometer adsorbent that it is quickly removed in fluorescence detection water body |
| CN106076295B (en) * | 2016-07-01 | 2018-08-21 | 四川大学 | It is a kind of can trivalent chromium and the preparation method of magnetic nanometer adsorbent for quickly removing it in fluorescence detection water body |
| CN108219773A (en) * | 2016-12-23 | 2018-06-29 | 泰山医学院 | Pyridine [1,2-a] and benzimidizole derivatives class Hg2+Ratio fluorescent probe and its application |
| CN110498803A (en) * | 2019-09-06 | 2019-11-26 | 山东师范大学 | A kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine |
| CN110498803B (en) * | 2019-09-06 | 2021-01-08 | 山东师范大学 | Compound based on rhodamine hydrazide structure and preparation method and application thereof |
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