CN104072754A - Water-soluble polymer probe capable of carrying out visual colorimetric detection onto copper ions as well as preparation method and application thereof - Google Patents
Water-soluble polymer probe capable of carrying out visual colorimetric detection onto copper ions as well as preparation method and application thereof Download PDFInfo
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- CN104072754A CN104072754A CN201410318003.XA CN201410318003A CN104072754A CN 104072754 A CN104072754 A CN 104072754A CN 201410318003 A CN201410318003 A CN 201410318003A CN 104072754 A CN104072754 A CN 104072754A
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Abstract
The invention belongs to the technical fields of material preparation and metal ion detection, relates to rhodamine B-based water soluble polymer probes for directly carrying out Cu<2+> visual colorimetric detection in a water medium and Cu<2+> test paper based on the water soluble polymer probes. The rhodamine B-based water soluble polymer probes are formed by modifying carboxyl-terminated polyethylene glycol by rhodamine B derivatives, have good water solubility, can selectively detect Cu<2+> in a pure water medium, and can achieve the visual detection effect by virtue of color change of detected liquor from being colorless to being colored.
Description
Technical field
The invention belongs to material preparation and metal ion detection technical field, relate to a class directly water-soluble polymers probe and the copper ion test paper based on this polymer probe of visual colorimetric determination detection cupric ion in water medium.
Background technology
As modal heavy metal ion, cupric ion is one of requisite trace element in organism, and it has vital role aspect hemopoietic function, anti-oxidant function and the various enzymes of human body synthetic.But in organism, the copper of excess intake can cause metabolic imbalance, may cause a series of diseases, as Wilson syndromes and Menkes syndromes etc.Therefore, to Cu in water surrounding
2+detect research and become the focus that people pay close attention to.
Current conventional detection of heavy metal ion method, as atomic absorption spectrometry, atomic emission spectrometry and electrochemical method etc. exist the shortcomings such as instrument is expensive, running cost is high, analytical procedure is complicated, is difficult to meet the actual demand of field quick detection.Therefore, efficient Cu easily
2+detection technique and product research arouse great concern.The advantages such as colorimetric probe method has fast response time, highly sensitive, selectivity good, easy handling.Rhodamine derivative has longer excitation wavelength and emission wavelength, larger molar extinction coefficient, higher fluorescence quantum yield and the excellent photophysics character such as optical stability preferably, therefore from [J. Am. Chem. Soc. such as Dujols in 1997,1997,119,7386-7387] report rhodamine B hydrazides success selectivity identification Cu
2+since, the rhodamine derivative small molecules of number of different types is synthesized out, and successfully for Cu
2+detection.Yet, because most rhodamine derivative small molecules are insoluble in water, need to add organic cosolvent and just can carry out the detection of Heavy Metals in Water Environment ion, the use of organic cosolvent has increased again the potential of contaminate environment may.Therefore, research and develop a kind of organic cosolvent that do not rely on and realize Cu in water
2+the efficient convenient probe that detects and can bore hole identification will have great actual application value.
The present invention selects water-soluble polymers polyoxyethylene glycol (PEG) as carrier, by polymer modification method, rhodamine B derivative unit is connected to PEG molecular chain-end with covalent linkage form, synthesized a kind of new rhodamine B based polyalcohol probe, this probe shows good solubility in water, can be by visual colorimetry to the Cu in water medium
2+realize high efficiency selected identification, and there is reversibility.Such polymer-coated is prepared into Test paper at substrate surface, can realizes Cu
2+convenient qualitative detection.
Summary of the invention
The object of this invention is to provide a kind of can visual detection, can recycle, can be directly in water medium to Cu
2+realize rhodamine B base water-soluble polymers probe of selectivity detection and preparation method thereof.Meanwhile, provide a kind of detected Cu that utilizes this polymer probe to prepare
2+portable test paper.
Technical scheme of the present invention is: a class can detect Cu by visual colorimetric determination
2+water-soluble polymers probe, structural formula is as follows:
In formula, n is 90 ~ 1136.
The preparation method of foregoing water-soluble polymers probe, is to carry out modified-reaction with the carboxylated polyoxyethylene glycol in 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone opposite end, and step is as follows:
(1) rhodamine B hydrazides and 2,4-Dihydroxy benzaldehyde are added in solvent, back flow reaction, is cooled to room temperature, and suction filtration obtains 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone;
(2) by 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, hold carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent to add in solvent, 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, to hold the mol ratio of carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent be 2.2:1:0.5:2.2, room temperature reaction 24 hours, purify, obtain target product.
Foregoing preparation method, preferably scheme is, the described solvent of step (1) is selected dehydrated alcohol or methyl alcohol.
Foregoing preparation method, preferably scheme is, the described solvent of step (2) is selected methylene dichloride.
Foregoing preparation method, preferably scheme is, the described catalyzer of step (2) is selected DMAP (DMAP).
Foregoing preparation method, preferably scheme is, the described water-retaining agent of step (2) is selected N, N '-dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl) phosphinylidyne diimine (EDC).
The present invention also provides Cu in a kind of water medium
2+test paper, is utilized solvent solution-forming through spraying or is soaked by described water-soluble polymers probe to be overlying on substrate surface and to make.
Cu in foregoing water medium
2+test paper, preferably scheme is, described solvent is water, methyl alcohol, ethanol, Virahol, methylene dichloride, chloroform or their mixed solution.
Cu in foregoing water medium
2+test paper, preferably scheme is, described base material is selected test paper, non-woven fabrics, cellulose membrane, polymeric film or starch film.
Cu in foregoing water medium
2+test paper, preferably scheme is, water-soluble polymers probe solution concentration is 0.1g/L ~ 20g/L.
The preparation method of rhodamine B base water-soluble polymers probe provided by the invention, first synthesize 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, then 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone reacts with the carboxylated polyoxyethylene glycol of end, and step is as follows: (1) rhodamine B hydrazides reference [Org. Lett., 2006,13,2863-2866] method introduced is synthetic.(2) method of holding carboxylated polyoxyethylene glycol reference [Polym. Bull., 1980,3,347-352] to introduce is synthetic.(3) rhodamine B hydrazides and 2,4-Dihydroxy benzaldehyde are added in solvent, back flow reaction, is cooled to room temperature, and suction filtration obtains 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, and described solvent is selected dehydrated alcohol or methyl alcohol; (4) by 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, hold carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent to add in solvent, wherein, 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, to hold the mol ratio of carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent be 2.2:1:0.5:2.2, room temperature reaction 24 hours, purifies, and obtains target product.
Rhodamine B base water-soluble polymers of the present invention is as Cu
2+probe is to the Cu in water medium
2+there are higher selectivity and sensitivity.Generally water-soluble polymers of the present invention is made into the aqueous solution, pH is controlled at 6 ~ 9 scopes, by observing colour-change to Cu
2+detect and identification, along with Cu
2+the increase of concentration, solution colour is deepened gradually, then in solution, adds after ethylenediamine tetraacetic acid (EDTA) radical ion ethylenediamine tetraacetic acid (EDTA) radical ion and Cu
2+in conjunction with, solution is become colorless by coloured, and that has realized probe can inverse operation.Strength of solution can determine by test condition, and for water-soluble polymers of the present invention, can be made into concentration is 0.005g/L ~ 1.0g/L, and conventional test concentrations can be made into 0.02g/L ~ 0.5g/L.Concrete test can adopt visual colorimetry or utilize standard working curve to extrapolate Cu
2+concentration.For obtaining more accurate result, can utilize ultraviolet visible spectrophotometry to test.
Rhodamine B base water-soluble polymers of the present invention can be made easily and detect Cu
2+test paper.Polymkeric substance of the present invention can be made into certain density solution, direct spraying or soak and be overlying on substrate surface and make Test paper, drying or naturally dry rear use.Obtain solution can select water, methyl alcohol, ethanol, Virahol, methylene dichloride, chloroform or their mixed solution as solvent, strength of solution can be determined by the colour-change degree of test paper, be generally 0.1g/L ~ 20g/L, base material can be selected test paper, non-woven fabrics, cellulose membrane, polymeric film or starch film etc.By observing the variation of test paper color, realize Cu
2+convenient qualitative detection.
Advantage of the present invention is: (1) rhodamine B base of the present invention water-soluble polymers water soluble, without adding organic cosolvent, by bore hole, observing aqueous solution colour-change can be to the Cu in water medium
2+realize efficient identification, to other metal ion (Ba in water sample
2+, Cd
2+, Co
2+, Cr
3+, Fe
2+, Fe
3+, Hg
2+, Mn
2+, Pb
2+, Zn
2+deng) immunity from interference strong, there is highly selective, this polymer probe has reversible operability simultaneously, can be recycled; (2) such polymer probe speed of response is fast, the time of response in 20s, Cu
2+concentration is greater than 5.0x10
-7mol/L can observe by bore hole the generation of red-purple color; (3) polymer probe of the present invention have that raw material is easy to get, synthesis technique is simple, selectivity good, highly sensitive, fast response time, low cost and other advantages, be applicable to production application; (4) Cu of the present invention
2+test paper, cheap, easy to use, be applicable to routine use.
Accompanying drawing explanation
Fig. 1 is the synthetic route of water-soluble polymers probe of the present invention (PEG10000Rh);
Fig. 2 adds the uv-visible absorption spectrum figure of different metal ion in the prepared aqueous solutions of polymers of embodiment;
Fig. 3 is that the prepared aqueous solutions of polymers of embodiment adds Cu under disturbance metal ion exists
2+after photon absorbing intensity change histogram;
Fig. 4 is that the prepared polymkeric substance of embodiment is to Cu
2+the response of reversible absorbancy, wherein (a) be that the absorbancy of the prepared aqueous solutions of polymers of embodiment responds, and (b) for the prepared aqueous solutions of polymers of embodiment, adds Cu
2+after absorbancy response, (c) for the prepared aqueous solutions of polymers of embodiment, add Cu
2+add again the absorbancy response after ethylenediamine tetraacetic acid (EDTA) radical ion, (d) for the prepared aqueous solutions of polymers of embodiment, add successively Cu
2+, ethylenediamine tetraacetic acid (EDTA) radical ion and Cu
2+after absorbancy response;
Fig. 5 adds different concns Cu in the prepared aqueous solutions of polymers of embodiment
2+after uv-visible absorption spectrum figure;
Fig. 6 is that the photon absorbing intensity of the prepared aqueous solutions of polymers of embodiment is with Cu
2+the change curve of concentration.
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described, and protection content of the present invention is not limited to following examples.Do not deviating under the spirit and scope of inventive concept, variation and advantage that those skilled in the art can expect are all included in the present invention.
Synthesizing of embodiment 1 water-soluble polymers probe (PEG10000Rh)
(1) 2, synthesizing of 4-Dihydroxy benzaldehyde rhodamine B acylhydrazone: by 0.69g rhodamine B hydrazides and 0.41g 2,4-Dihydroxy benzaldehyde adds in 25mL dehydrated alcohol, back flow reaction 8 hours, be cooled to room temperature, suction filtration, obtains 2 after vacuum-drying, 4-Dihydroxy benzaldehyde rhodamine B acylhydrazone 0.64g, productive rate 75%;
Nuclear magnetic resonance hydrogen spectruming determining:
1h-NMR (400MHz, CDCl
3), δ (ppm): 1.14 (t, 12H, J=7 Hz), 3.32 (q, 8H, J=7.2 Hz), 6.28 (dd, 2H, J=8.8 Hz, J=2.4 Hz), 6.31 (dd, 1H, J=8.8 Hz, J=2.4 Hz), 6.35 (d, 1H, J=2.4 Hz), 6.47 (d, 2H, J=2.4 Hz), 6.50 (d, 2H, J=8.8 Hz), 6.96 (d, 1H, J=8.4 Hz), 7.18 (dd, 1H, J=6.4 Hz, J=1.6 Hz), 7.51 (m, 2H), 7.97 (dd, 1H, J=6.8 Hz, J=1.6 Hz), 9.19 (s, 1H), 11.02 (s, 2H),
Carbon-13 nmr spectra is measured:
13c-NMR (100MHz, CDCl
3), δ (ppm): 12.6,44.3,66.7,98.1,103.5,105.5,107.1,108.2,112.3,123.2,124.1,128.1,128.5,130.2,133.1,133.3,149.1,150.6,153.6,154.1,159.0,160.7,164.1.
(2) water-soluble polymers probe (PEG10000Rh) is synthetic: by 1.02 g Carboxylic-terminated Polyethylene Glycol 10000,0.127 g 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone and 10 mg DMAP add in 20 ml anhydrous methylene chlorides, then add rapidly 45.4 mg DCC, stirring at room reaction 24 hours, filter, by dichloromethane rinse, after filtrate is concentrated, in 50 ml ether, precipitate, suction filtration obtains white solid product 0.86 g, productive rate 76% by vacuum-drying.
The synthetic route of water-soluble polymers probe (PEG10000Rh) as shown in Figure 1.
Cu in embodiment 2 water mediums
2+detection
Get embodiment 1 synthesized water-soluble polymers PEG10000Rh and be dissolved in deionized water, be made into concentration and be the aqueous solution of 56.6 mg/L as storing solution, wherein the concentration of Rhodamine Derivatives functional group is 10 μ M.
Get 12 parts of 3mL storing solutions as detecting liquid, add respectively wherein the Ba of 5 equivalents
2+, Cd
2+, Co
2+, Cr
3+, Fe
2+, Fe
3+, Hg
2+, Mn
2+, Pb
2+, Zn
2+, Cu
2+and blank, find only to add Cu
2+detection liquid occurred by colourless, to mauve colour-change, to have realized Cu
2+the bore hole identification detecting.Carry out respectively ultraviolet visible spectrophotometry test, except adding Cu
2+detection liquid outside there is strong absorption peak in 560nm place, add the absorbancy of detection liquid of other ion all less than too large variation (as shown in Figure 2).To being added with the Cu that adds 5 equivalents in the detection liquid of other metal ion
2+, detecting liquid color by the colourless red-purple that becomes, Fig. 3 adds Cu for detecting liquid under disturbance metal ion exists
2+after at the photon absorbing intensity at 560nm place, change histogram, show that other coexistent metallic ion does not obviously change probe of the present invention to Cu
2+detection effect, embodied the interference free performance that polymer probe of the present invention is stronger.
To being added with 5 equivalent Cu
2+detection liquid in add the ethylenediamine tetraacetic acid (EDTA) radical ion of 5 equivalents, the color of solution is by adding Cu
2+red-purple afterwards becomes colorless, and absorbancy is also almost got back to and do not added Cu
2+level before, then add 5 equivalent Cu
2+, the color of solution becomes again red-purple, again occurs strong absorption peak (as shown in Figure 4) at 560nm place, shows that polymer probe of the present invention has good reversibility.
Get 3mL storing solution and add in quartz colorimetric utensil as detecting liquid, add wherein the Cu of different equivalents
2+, along with adding Cu
2+the increase of equivalent, solution colour is from the colourless red-purple that becomes, and absorbancy also increases (as shown in Figure 5) thereupon gradually.This polymer probe is to Cu
2+the corresponding time of colour developing be less than 20s, work as Cu
2+while reaching 1.5 equivalent, absorbancy reaches maximum value (as shown in Figure 6), shows that this polymkeric substance is a kind of Cu that can visual colorimetric determination detects
2+efficient probe.
Cu in embodiment 3 water mediums
2+test paper and application thereof
The ethanolic soln of preparation embodiment 1 synthesized polymkeric substance, concentration is 0.5g/L, is coated in the filter paper surface of 3x0.5 square centimeter, dries.With test paper, dip that concentration is respectively blank, every liter containing Cu
2+the aqueous solution of 0.1mg, 0.5mg, 1mg, test paper color becomes respectively incarnadine (0.1mg), light red (0.5mg), red-purple (1mg) from colourless (blank).
Of the present invention completing had benefited from fund assistance: the young and middle-aged scientist's scientific research bonus pool (BS2012CL009,2011CL011,2011CL012) in Shandong Province.
Claims (10)
1. a class can detect Cu by visual colorimetric determination
2+water-soluble polymers probe, it is characterized in that, structural formula is as follows:
In formula, n is 90 ~ 1136.
2. the preparation method of water-soluble polymers probe claimed in claim 1, is characterized in that, with the carboxylated polyoxyethylene glycol in 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone opposite end, carries out modified-reaction, and step is as follows:
(1) rhodamine B hydrazides and 2,4-Dihydroxy benzaldehyde are added in solvent, back flow reaction, is cooled to room temperature, and suction filtration obtains 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone;
(2) by 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, hold carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent to add in solvent, 2,4-Dihydroxy benzaldehyde rhodamine B acylhydrazone, to hold the mol ratio of carboxylated polyoxyethylene glycol, catalyzer, water-retaining agent be 2.2:1:0.5:2.2, room temperature reaction 24 hours, purify, obtain target product.
3. preparation method claimed in claim 2, is characterized in that, the described solvent of step (1) is selected dehydrated alcohol or methyl alcohol.
4. preparation method claimed in claim 2, is characterized in that, the described solvent of step (2) is selected methylene dichloride.
5. preparation method claimed in claim 2, is characterized in that, the described catalyzer of step (2) is selected DMAP (DMAP).
6. preparation method claimed in claim 2, is characterized in that, the described water-retaining agent of step (2) is selected N, N '-dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl) phosphinylidyne diimine (EDC).
7. Cu in a water medium
2+test paper, is characterized in that, is utilized solvent solution-forming through spraying or soaked to be overlying on substrate surface and to make by water-soluble polymers probe described in claim 1.
8. Cu in water medium claimed in claim 7
2+test paper, is characterized in that, described solvent is water, methyl alcohol, ethanol, Virahol, methylene dichloride, chloroform or their mixed solution.
9. Cu in water medium claimed in claim 7
2+test paper, is characterized in that, described base material is selected test paper, non-woven fabrics, cellulose membrane, polymeric film or starch film.
10. Cu in water medium claimed in claim 7
2+test paper, is characterized in that, water-soluble polymers probe solution concentration is 0.1g/L ~ 20g/L.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107652309A (en) * | 2017-11-08 | 2018-02-02 | 齐齐哈尔大学 | A kind of ultraviolet molecular probe of fluorescein rhodamine B copper ions and its synthesis and application method for open hole detection |
| CN111562259A (en) * | 2020-07-03 | 2020-08-21 | 江西省农业科学院农产品质量安全与标准研究所 | Method for preparing copper (II) ion visible probe and application thereof |
| CN111830021A (en) * | 2020-07-28 | 2020-10-27 | 江西省农业科学院农产品质量安全与标准研究所 | Test paper for detecting copper (II) ions with high selectivity and preparation method thereof |
| CN112159522A (en) * | 2020-10-09 | 2021-01-01 | 山东大学 | Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe and preparation method and application thereof |
| CN113845655A (en) * | 2021-10-20 | 2021-12-28 | 山东大学 | Water-soluble fluorescein polymer probe for mercury ion detection and preparation and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102020985A (en) * | 2010-09-28 | 2011-04-20 | 济南大学 | Method for manufacturing novel dendritic fluorescent chemosensor and application |
| CN102206223A (en) * | 2010-03-29 | 2011-10-05 | 清华大学 | Optical probe film and special-purposed organic dye for micro determination of copper ion content in water sample |
| CN103204997A (en) * | 2013-04-22 | 2013-07-17 | 江苏大学 | Preparation method of polyactic acid/polyethylene glycol biological hybrid material for PDT (photodynamic therapy) |
| CN103709321A (en) * | 2013-12-14 | 2014-04-09 | 聊城大学 | Rhodamine B based hydrophilic polymer probe for hyperchromic detection of Cu<2+> as well as preparation method and application thereof |
-
2014
- 2014-07-05 CN CN201410318003.XA patent/CN104072754A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206223A (en) * | 2010-03-29 | 2011-10-05 | 清华大学 | Optical probe film and special-purposed organic dye for micro determination of copper ion content in water sample |
| CN102020985A (en) * | 2010-09-28 | 2011-04-20 | 济南大学 | Method for manufacturing novel dendritic fluorescent chemosensor and application |
| CN103204997A (en) * | 2013-04-22 | 2013-07-17 | 江苏大学 | Preparation method of polyactic acid/polyethylene glycol biological hybrid material for PDT (photodynamic therapy) |
| CN103709321A (en) * | 2013-12-14 | 2014-04-09 | 聊城大学 | Rhodamine B based hydrophilic polymer probe for hyperchromic detection of Cu<2+> as well as preparation method and application thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107652309A (en) * | 2017-11-08 | 2018-02-02 | 齐齐哈尔大学 | A kind of ultraviolet molecular probe of fluorescein rhodamine B copper ions and its synthesis and application method for open hole detection |
| CN111562259A (en) * | 2020-07-03 | 2020-08-21 | 江西省农业科学院农产品质量安全与标准研究所 | Method for preparing copper (II) ion visible probe and application thereof |
| CN111830021A (en) * | 2020-07-28 | 2020-10-27 | 江西省农业科学院农产品质量安全与标准研究所 | Test paper for detecting copper (II) ions with high selectivity and preparation method thereof |
| CN112159522A (en) * | 2020-10-09 | 2021-01-01 | 山东大学 | Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe and preparation method and application thereof |
| CN112159522B (en) * | 2020-10-09 | 2021-08-06 | 山东大学 | Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe and preparation method and application thereof |
| CN113845655A (en) * | 2021-10-20 | 2021-12-28 | 山东大学 | Water-soluble fluorescein polymer probe for mercury ion detection and preparation and application thereof |
| CN113845655B (en) * | 2021-10-20 | 2022-06-24 | 山东大学 | Water-soluble fluorescein polymer probe for mercury ion detection and preparation and application thereof |
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Application publication date: 20141001 |