CN108586776A - The preparation and the application in ion detection of a kind of supermolecule polymer gel and its metal complex - Google Patents
The preparation and the application in ion detection of a kind of supermolecule polymer gel and its metal complex Download PDFInfo
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Abstract
Present invention design has synthesized a kind of supermolecule polymer gel, is in cyclohexanol, with column [5] aromatic hydrocarbons of naphthalimide functionalization（P5N）Based on, double 4,4 bipyridine salts（G）For object, and Subjective and Objective forms the supermolecule polymer TDPG with the aggregated-state induced fluorescence of yellow with equimolar than self assembly.A variety of cations, only Fe are separately added into supermolecule polymer TDPG3+、Hg2+The addition Fe that can make the fluorescent quenching of supermolecule polymer gel, therefore can be used in fluorescence identifying and adsorbing separation solution3+And Hg2+.It is separately added into Fe in supermolecule polymer TDPG3+And Hg2+, stable Metal-coordinated supramolecules Fe TDPG and Hg TDPG are obtained, it being capable of highly sensitive and highly selective detection identification F‑And Br‑.This recognition performance has important application value in ion identification field.
Description
Technical field
The present invention relates to a kind of supermolecule polymer gel more particularly to a kind of column [5] virtues with naphthalimide functionalization
It is the supermolecule polymer gel that object assembles with double 4,4 bipyridine salts based on hydrocarbon；The invention further relates to super based on this
The metal complex of Molecularly Imprinted Polymer gel；The present invention relates to supermolecule polymer gels and its metal complex in ion detection
In application.
Background technology
In the important role of the fields intermediate ion such as chemistry, biology, environment and molecule performer, for certain special in environment
The detection of lewis' acid with detach it is most important.Currently, people have been developed for the detection method of various ionic/molecular, and
And since fluorescence method has many advantages, such as easy to operate, quick, high sensitivity, have developed into ion identification predominantly detects hand
Section.However, in actual life, various beneficial to human body or harmful ion is mostly present in water phase, and reported can
It is to carry out in the solution mostly in the method being detected to ion, limitation is also compared to the detection of ion；And fluorine ion etc.
It is relatively difficult to its detection in water phase with larger hydration energy.
Invention content
The object of the present invention is to provide a kind of supermolecule polymer gels；
Separately there are one purposes by the present invention, are to provide a kind of metal complex based on above-mentioned supermolecule polymer gel；
It is a further aim of the invention providing above-mentioned supermolecule polymer gel and its Metal-coordinated supramolecules in ion
Application in detection.
One, supermolecule polymer gel
Supermolecule polymer gel of the present invention is column [5] aromatic hydrocarbons of main body naphthalimide functionalization in cyclohexanol（P5N）With
Double 4,4 bipyridine salts of object（G）Assembled with equimolar ratio, is labeled as TDPG.
Wherein, column [5] aromatic hydrocarbons of main body naphthalimide functionalization（P5N）Structural formula be：
n=1、2、3、4；
Double 4,4 bipyridine salts of object（G）Structure be as follows：
The assembly model of Subjective and Objective is as follows：
The Analysis on Mechanism that supermolecule polymer gel TDPG is formed below by nuclear-magnetism figure, nuclear-magnetism titration hydrogen spectrogram.Fig. 1 is
The moiety concentrations nuclear-magnetism figure of P5N.In Fig. 1, from（b）~（g）The concentration of P5N gradually increases, it can be found that H1-7 is moved to High-Field
It is dynamic, illustrate that there are π-π effects between the column aromatic hydrocarbons group of P5N and naphthalimide group and another molecule P5N.Fig. 2 is P5N and G
Nuclear-magnetism titrate hydrogen spectrogram.Wherein（a）P5N；（b）~（h）G containing different equivalents.From fig. 2 it can be seen that on object G
Hydrogen Proton Ha, Hb, Hc, Hd and He are to low field displacement, while the Hydrogen Proton H6 and H7 in main body P5N column aromatic hydrocarbons group is to High-Field
Displacement illustrates that object G pyridinium moieties enter the cavity of column aromatic hydrocarbons.Main body P5N and object G can be illustrated by the above phenomenon
It is assembled by host and guest's recognition reaction and π-π effects, to obtain supermolecule polymer frame material（TDPG）.
Two, the fluorescence response of supermolecule polymer TDPG
1, the fluorescence property of TDPG
Fig. 3 is the fluorescence spectrum of supermolecule polymer TDPG.As seen from Figure 3, supermolecule polymer TDPG has good
Fluorescence property, when excitation wavelength is 350nm, TDPG sends out yellow fluorescence（Launch wavelength 538nm）.
2, TDPG is to Fe3+And Hg2+Fluorescence identifying performance
In supermolecule polymer TDPG, it is separately added into the Mg of 10 times of equivalents2+, Ca2+, Cr3+, Fe3+, Co2+, Ni2+, Cu2+, Zn2 +, Ag+, Cd2+, Hg2+, Pb2+, Ba2+, Al3+, La3+, Eu3+（0.1M）Solution, it is found that Fe is only added3+And Hg2+It can make TDPG's
Fluorescent quenching, therefore, the Fe that TDPG can be used in single-minded selective fluorescence identifying solution3+And Hg2+。
Fluorescence titration experiment shows supermolecule polymer TDPG to Fe3+And Hg2+Minimum detection limit be respectively 9.19 ×
10-9 M、3.95×10-8M（See Fig. 3 c and 3d）.
3, TDPG is to Fe3+And Hg2+Fluorescence identifying basis mechanism
By infrared experiment show that Fe is added in TDPG3+When, the-C=peaks H and-C=peaks O of TDPG is by 2923 cm-1With
1632 cm-1It is moved to 2930 cm-1With 1668 cm-1（See Fig. 4）, illustrate Fe3+Cation-π occurs with the naphthalimide of P5N to make
With to form stable complex.As addition Hg2+When ,-C=peaks N of object G pyridyl groups are by 1461 cm-1It is moved to 1457
cm-1Outside（See Fig. 5）, illustrate Hg2+It is coordinated with the nitrogen-atoms on the pyridine of G, forms stable complex.
Since supermolecule polymer TDPG can be with Fe3+And Hg2+It is coordinated to form complex compound by various chemical bonds, therefore,
TDPG can be realized to Fe in solution3+And Hg2+Efficiently separate and remove.
Four, Metal-coordinated supramolecules
1, the synthesis of Metal-coordinated supramolecules
In supermolecule polymer TDPG, it is separately added into the Fe of 2 times of moles of supermolecule polymer3+And Hg2+, after heating for dissolving
It is cooled to room temperature, obtains stable Metal-coordinated supramolecules gel, be labeled as Fe-TDPG and Hg-TDPG.
2, Metal-coordinated supramolecules are to F-And Br-Highly sensitive detection
In Metal-coordinated supramolecules Fe-TDPG, it is separately added into Cl-, Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, N3 -, OH-,
SCN-, ClO4 -（0.1M）Solution, it is found that F is only added-The fluorescence of Fe-TDPG can be made to open（See Fig. 6 a）.
In Metal-coordinated supramolecules Hg-TDPG, it is separately added into Cl-, Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, N3 -,
OH-, SCN-, ClO4 -（0.1M）Solution, it is found that Br is only added-The fluorescence of Hg-TDPG can be made to open and send out pink fluorescence
（See Fig. 6 b）.
In conclusion by competitive coordination mechanism, we design a kind of supermolecule polymer frame material of synthesis
（TDPG）With metal supermolecular polymeric frame frame material（M-TDPG）Can the response of more than enough object and highly sensitive detection detach it is a variety of from
Son.And this competitiveness distinguishing complex can also be used as a kind of fluorescent switch of " ON-OFF-ON " formula, and this recognition performance exists
Ion identification field has important application value.
Description of the drawings
Fig. 1 is the concentration nucleus magnetic hydrogen spectrum figure of P5N.
The nuclear-magnetism that Fig. 2 is P5N and G titrates hydrogen spectrogram.
Fig. 3 is TDPG to Fe3+And Hg2+Fluorescence titration figure.
Fig. 4 is that TDPG identifies Fe3+F is identified with Fe-TDPG-Infrared spectrogram.
Fig. 5 is that TDPG identifies Hg2+Br is identified with Hg-TDPG-Infrared spectrogram.
Fig. 6 is Fe-TDPG and Hg-TDPG to F-And Br-Fluorescence titration.
Specific implementation mode
The preparation of supermolecule polymer of the present invention, metal complex and application are done further below by specific embodiment
Explanation.
Embodiment 1, supermolecule polymer gel（TDPG）Synthesis
（1）The synthesis of main body P5N：In 50ml acetonitriles, 0.58g is added（5×10-3mol）Column [5] aromatic hydrocarbons P5 of bromo,
0.43g（1.5×10-3mol）Naphthalamide derivatives react 48h at 80 DEG C；It waits for being cooled to room temperature after reaction, revolve
Solvent is evaporated off, sample upper prop is mixed, with petroleum ether:Ethyl acetate=10:1~10:5（v/v）Elution, it is solidifying to obtain yellow solid product
Glue factor P5N；Yield is 75.6%.
（2）The synthesis of object G：1.9801g is added in 100ml acetonitriles（1.89 g, 6.3 mmol）1,10- dibromo-decanes
With 4,4'- bipyridyls（5.56g, 35.7 mmol）, it is stirred at reflux at 90 ~ 100 DEG C 18 hours；It is cooled to room temperature, is leaked with Bu Shi
Bucket is filtered, and is washed 3 ~ 5 times with acetonitrile and ethyl alcohol, and it is guest compound G to obtain 3.3g pistac powdery products.Production
Rate is 86%.
（3）Supermolecule polymer gel（TDPG）Synthesis：In 0.2ml cyclohexanol, main body P5N is added（0.0050g,
4.5×10-6mol）, object G（0.0047g, 4.5 × 10-6mol）, heating makes it completely dissolved, then cools to room temperature, obtain
Stable supermolecule polymer gel（TDPG）, there is blue-fluorescence.
Embodiment 2, supermolecule polymer TDPG are to Fe3+And Hg2+Fluorescence identifying
In supermolecule polymer gel TDPG, it is separately added into the Mg of 10 times of equivalents2+, Ca2+, Cr3+, Fe3+, Co2+, Ni2+, Cu2 +, Zn2+, Ag+, Cd2+, Hg2+, Pb2+, Ba2+, Al3+, La3+, Eu3+（0.1M）Solution observes the variation of solution fluorescence.As a result it sends out
It is existing, Fe is only added3+、Hg2+When, the fluorescent quenching of TDPG, thus by Fe3+、Hg2+It is identified from numerous cations.
Embodiment 3, supermolecule polymer gel are to Fe3+And Hg2+Efficiently separate and remove
Configuration concentration is 1 × 10 first-5M Fe3+And Hg2+Each 5mL of solution, 0.1mg is added in each solion（5×10-8mol）TDPG xerogel shakes 30 minutes, is centrifuged 20 minutes with the rotating speed of 8000r/min, and residual supernatant is taken to be ICP（Inductance
Coupled plasma）.The results show that TDPG is to Hg2+And Fe3+The adsorption efficiency of ion is shown in Table 1：
。
Embodiment 4, Metal-coordinated supramolecules（M-TDPG）Preparation and application
Two parts of P5N are taken respectively（0.005g）、G（0.005g）, it is added in 0.5ml cyclohexanol, then be separately added into 2 times of equivalents
Fe3+And Hg2+, dissolve by heating and be cooled to room temperature, obtain stable Metal-coordinated supramolecules Fe-TDPG and Hg-TDPG.
In Metal-coordinated supramolecules Fe-TDPG, it is separately added into Cl-, Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, SCN-,
CN-, ClO4 -If the fluorescence of Metal-coordinated supramolecules Fe-TDPG restores, that illustrate to be added is F-；If metal supermolecular is matched
The fluorescence for closing object Fe-TDPG does not restore, then illustrate to be added is other anion.
In Metal-coordinated supramolecules Hg-TDPG, it is separately added into Cl-, Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, SCN-,
CN-, ClO4 -If the fluorescence of Metal-coordinated supramolecules Hg-TDPG becomes pink, that illustrate to be added is Br-If metal oversubscription
The fluorescence of sub- complex Hg-TDPG does not change, then illustrates that it is other anion to be added.
Claims (7)
1. a kind of supermolecule polymer gel is in cyclohexanol, column [5] aromatic hydrocarbons and object of main body naphthalimide functionalization are double
4,4 bipyridine salts form the supermolecule polymer with the aggregated-state induced fluorescence of yellow than self assembly with equimolar；
The structural formula of column [5] aromatic hydrocarbons of the main body naphthalimide functionalization is：
n=1、2、3、4；
The structural formula of double 4,4 bipyridine salts of the object is as follows：
。
2. supermolecule polymer gel as described in claim 1, it is characterised in that：Column [5] virtue of main body naphthalimide functionalization
Hydrocarbon is 1.5 ~ 2.5g/mL with content of double 4,4 bipyridine salts of object in system.
3. supermolecule polymer gel as described in claim 1 is used for fluorescence identifying Fe3+And Hg2+, it is characterised in that：In supermolecule
In polymer gel, it is separately added into Mg2+, Ca2+, Cr3+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Ag+, Cd2+, Hg2+, Pb2+, Ba2+,
Al3+, La3+, Eu3+Solution, only Fe3+、Hg2+Addition can make the fluorescent quenching of supermolecule polymer gel.
4. supermolecule polymer gel as described in claim 1 is used for the Fe in adsorbing separation solution3+And Hg2+。
5. a kind of Metal-coordinated supramolecules based on supermolecule polymer as described in claim 1, are in supermolecule polymer
In gel, it is separately added into the Fe of 2 times of moles of supermolecule polymer3+、Hg2+, room temperature is cooled to after heating for dissolving, is obtained steady
Fixed Metal-coordinated supramolecules gel Fe-TDPG, Hg-TDPG.
6. Metal-coordinated supramolecules as claimed in claim 5 F for identification-, it is characterised in that：In Metal-coordinated supramolecules
In Fe-TDPG, it is separately added into Cl-, Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, SCN-, CN-, ClO4 -If metal supermolecular coordinates
The fluorescence of object Fe-TDPG restores, then that illustrate to be added is F-；If the fluorescence of Metal-coordinated supramolecules Fe-TDPG does not restore,
Then illustrate to be added is other anion.
7. Metal-coordinated supramolecules as claimed in claim 5 Br for identification-, it is characterised in that：Gold as claimed in claim 6
Belong to super molecular complex Br for identification-, it is characterised in that：In Metal-coordinated supramolecules Hg-TDPG, it is separately added into Cl-,
Br-, I-, F-, AcO-, H2PO4 -, HSO4 -, SCN-, CN-, ClO4 -If the fluorescence of Metal-coordinated supramolecules Hg-TDPG becomes powder
Red, that illustrate to be added is Br-If the fluorescence of Metal-coordinated supramolecules Hg-TDPG does not change, illustrate addition
It is other anion.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109294558A (en) * | 2018-10-30 | 2019-02-01 | 西北师范大学 | Subjective and Objective assembling supermolecular gel and its preparation and application based on pyromellitic trimethylsilyl chloride functionalization |
| CN109400900A (en) * | 2018-10-30 | 2019-03-01 | 西北师范大学 | Supermolecular gel based on the assembling of column [5] aromatic hydrocarbons Subjective and Objective and its application in detection and absorption iron ion |
| CN110540656A (en) * | 2019-09-30 | 2019-12-06 | 河南工业大学 | Preparation method and application of photoinduced electron transfer supramolecular nanoparticles |
| CN110790940A (en) * | 2019-10-29 | 2020-02-14 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
| CN110982086A (en) * | 2019-12-18 | 2020-04-10 | 西北师范大学 | Host-guest assembled supramolecular polymer, preparation thereof and application thereof in identifying mercury ions |
| CN111116933A (en) * | 2020-01-03 | 2020-05-08 | 西北师范大学 | Supramolecular polymer and application thereof in mercury ion detection |
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| US20050059834A1 (en) * | 2003-09-16 | 2005-03-17 | Ming Zhou | Dendritic supramolecular compound for electrochemiluminescent analysis |
| CN103374132A (en) * | 2013-07-12 | 2013-10-30 | 中科院广州化学有限公司 | Preparation and application of metal ion directly induced fluorescent supramolecular gel |
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| CN109294558A (en) * | 2018-10-30 | 2019-02-01 | 西北师范大学 | Subjective and Objective assembling supermolecular gel and its preparation and application based on pyromellitic trimethylsilyl chloride functionalization |
| CN109400900A (en) * | 2018-10-30 | 2019-03-01 | 西北师范大学 | Supermolecular gel based on the assembling of column [5] aromatic hydrocarbons Subjective and Objective and its application in detection and absorption iron ion |
| CN109400900B (en) * | 2018-10-30 | 2021-02-05 | 西北师范大学 | Supermolecule gel assembled based on column [5] arene main-object and application thereof in detection and adsorption of iron ions |
| CN109294558B (en) * | 2018-10-30 | 2021-02-19 | 西北师范大学 | Host-guest assembled supramolecular gel based on trimesoyl chloride functionalization and preparation and application thereof |
| CN110540656A (en) * | 2019-09-30 | 2019-12-06 | 河南工业大学 | Preparation method and application of photoinduced electron transfer supramolecular nanoparticles |
| CN110790940A (en) * | 2019-10-29 | 2020-02-14 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
| CN110790940B (en) * | 2019-10-29 | 2021-06-11 | 西北师范大学 | Bipatripodous supramolecular polymer organogel and preparation and application thereof |
| CN110982086A (en) * | 2019-12-18 | 2020-04-10 | 西北师范大学 | Host-guest assembled supramolecular polymer, preparation thereof and application thereof in identifying mercury ions |
| CN110982086B (en) * | 2019-12-18 | 2021-07-23 | 西北师范大学 | Host-guest assembled supramolecular polymer, preparation thereof and application thereof in identifying mercury ions |
| CN111116933A (en) * | 2020-01-03 | 2020-05-08 | 西北师范大学 | Supramolecular polymer and application thereof in mercury ion detection |
| CN111116933B (en) * | 2020-01-03 | 2021-09-24 | 西北师范大学 | Supramolecular polymer and application thereof in mercury ion detection |
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