CN105753662A - Pillar[5]arene and 2-hydroxy-3-naphthoic acid complex and preparation thereof and application in detecting iron ions and fluorine ions - Google Patents
Pillar[5]arene and 2-hydroxy-3-naphthoic acid complex and preparation thereof and application in detecting iron ions and fluorine ions Download PDFInfo
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Abstract
The invention provides a pillar[5]arene and 2-hydroxy-3-naphthoic acid complex.Copolymerized pillar[5]arene serves as a subject, 2-hydroxy-3-naphthoic acid serves as an object, C-H......pi and electrostatic attraction serve as driving force, partial 2-hydroxy-3-naphthoic acid provided with negative charges is included into a cavity of pillararene in an alkaline environment, the assembling process of the subject and the object is completed, and the stable pillar[5]arene and 2-hydroxy-3-naphthoic acid complex is formed.Iron ions are added to an alkaline aqueous solution of the complex, and the subject and the object are subjected to fluorescence quenching; fluorine ions are added, a complex is formed by the fluorine ions and the iron ions, so that the iron ions are separated from the cavity of copolymerized pillar[5]arene, and molecular fluorescence of the complex is reopened.Therefore, Fe<3+> can be determined through the pillar[5]arene and 2-hydroxy-3-naphthoic acid complex, and F<-> can be continuously identified through fluorescence quenching of the solution.
Description
Technical field
The present invention relates to a kind of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex；The present invention also relates to the application in detection iron ion continuously and fluorine ion of this complex, belongs to ion detection technical field.
Background technology
Ferro element is one of requisite element constituting human body, and iron deficiency influences whether health and the growth of human body, and maximum impact is i.e. hypoferric anemia.But, iron is once absorbed by the body, and except part is with losing blood in addition to loss, seldom has other excretion pathwaies.Internal unnecessary iron stores with the form of ferritin, and Blood lipids too much can increase the danger suffered from a heart complaint.Research finds, the combination of hemoglobin and oxygen, separating, the relation with iron is very close, and iron too much can promote that oxygen radical increases, and body is had significantly super oxidation, iron promoter that the free radical of instability too much can be promoted to destroy healthy body tissue by oxygen radical.Additionally, the ferritin in blood makes heart disease deteriorate with cholesterol interaction energy, the popular feeling popular name for incidence of disease that ferritin is high is the twice of normal person.Scientific research personnel points out, in all cardiopathic hazards, high ferritin is more dangerous than high cholesterol, hypertension and diabetes.Ferric ion may cause the free radical that some are the most popular to people, thus causes a series of problem.Taken one with another may be relatively big with liver relation, the most associated beta Cell of islet, nerve cell are also possible to be affected.The Testing index of other drug and part disease may be caused certain interference by the ferric ion in blood.Liver stores and fixing substantial amounts of ferro element under normal circumstances, as at liver, iron occurs that superfluous calmness then may cause hepatocellular damage and liver fibrosis, participate in oncogenic process by 3 mechanism such as oxidative stress induction, tumor growth promotion and immune system modifications simultaneously.Owing to iron relates to substantial amounts of iron enzyme and iron protein, so being a kind of indispensable element for most biology, but it is the most also poisonous.Iron is readily available and loses electronics, and it can promote that the generation of free radical, this free radical can damage cell membrane, protein and DNA, causes cell death and causes the injury to tissue.The iron ion of excess enters human body and also brings along danger band, and the increase that iron is a small amount of in reticuloendothelial cell just can affect the signal transmission of cell, and the iron accumulation in city, Nao Zhongmou district is relevant with many neurogenic diseases.Iron can promote the propagation of unwanted cells and the generation of free radical, causes histologic lesion or increases angiocardiopathy.
For a long time, people do not cause enough attention to the harm of drinking water iron ion.The higher reason of drinking water iron concentration is the most, it can be common that use underground water to do the water source of drinking water, and the meeting iron ion in rock stratum is dissolved in water, in Fe2 +, when after itself and air contact, aoxidized, become Fe3 +.It addition, the corrosion of water supply system, such as pipeline, ion-exchanger are outmoded, aging；Anticorrosive coat Spalling, has little time the reasons such as repairing, cause iron ion enter to and water source.Drink such water for a long time and certainly human body is had a certain degree of impact.Therefore, detect the concentration of iron ions from drinking water in time, have highly important meaning for health.Currently for the detection of iron ion, generally use the detection of development process method, or measure by oxidation-reduction method.These detection methods need the detection time longer, detect inconspicuous or to detect by more complicated instrument.
Fluorine ion is a kind of nonmetalloid, after human body stores the fluorine of excess, the poisoning of fluorine can be caused, mainly showing as tooth to turn yellow, blackening, leg is X or O type, bend forward waist hunchback or arm intelligence is played and can not be stretched, poisoning the lighter causes den tal fluorosis, severe one fluorosis of bone occur, even completely loses labour capacity and self care ability.Fluorine poisoning person once suffers from and the most forever becomes disease, and medicine can only slow down increasing the weight of of the state of an illness.Therefore, the existence at pure water middle detection fluorine ion mutually is a very important field.
Post aromatic hydrocarbons has shown outstanding effect as the macrocycle molecule that a class is new in terms of host-guest chemistry.Itself and the Subjective and Objective bonding action of guest molecule and self assembly behavior all become the focus of research.By the modification of coupled columns aromatic hydrocarbons structure, many host-guest chemistry systems are well developed.It is known that copolymerization post 5 aromatic hydrocarbons provides a good cavity structure, so the guest molecule with suitable construction size can penetrate into the result reaching host-guest inclusion in its cavity.
2-hydroxyl-3-naphthoic acid self is exactly a fluorophor under alkaline environment, its complex being self-assembly of in aqueous with post 5 aromatic hydrocarbons, and as new fluorescent optical sensor, and make its functionalization, thus can be as good fluorescent sensing material in the detection of ion.
Summary of the invention
It is an object of the invention to the character according to post aromatic hydrocarbons, it is provided that a kind of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex；
It is a further object of the present invention to provide the preparation method of a kind of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex；
A prior purpose of the present invention, it is simply that iron ion and the application of fluorine ion in detection aqueous phase of a kind of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is provided.
One, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex
The preparation of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, it is by post 5 aromatic hydrocarbons, 2-hydroxyl-3-naphthoic acid is dissolved in the water, the effect adding NaOH(NaOH is to make 2-hydroxyl-3-naphthoic acid become corresponding sodium salt, solubility in water is more preferable), 1 ~ 3min is stirred at room temperature, obtains post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex aqueous solution.
Post 5 aromatic hydrocarbons is 1:1 with the mol ratio that mol ratio is 1:2,2-hydroxyl-3-naphthoic acid and NaOH of 2-hydroxyl-3-naphthoic acid.
In order to study copolymerization post 5 aromatic hydrocarbons and the self assembling process of 2-hydroxyl-3-naphthoic acid and Inclusion property, we have done one-dimensional nuclear-magnetism and nuclear-magnetism titration.
Fig. 1 is the one-dimensional nuclear-magnetism titration collection of illustrative plates of copolymerization post 5 aromatic hydrocarbons and guest molecule 2-hydroxyl-3-naphthoic acid self assembly.Figure can be seen that main column 5 aromatic hydrocarbons, guest molecule 2-hydroxyl-3-naphthoic acid, and Subjective and Objective assemble after the change that occurs of corresponding Hydrogen Proton displacement.When adding the object 2-hydroxyl-3-naphthoic acid of twice equivalent in the deuterium-oxide solution containing copolymerization post 5, on guest molecule, Hydrogen Proton moves to High-Field, and these chemical shifts prove completing of inclusion process.
Fig. 2 is the concentration titrations nuclear-magnetism figure of different mol ratio post 5 aromatic hydrocarbons and guest molecule.From figure 2 it can be seen that along with the increase of guest molecule concentration, when adding the guest molecule of 1 times of equivalent, H on guest moleculea-HfMoving to High-Field, this is owing to inclusion guest molecule has the shielding action of induction to be caused.Also demonstrating the naphthalene nucleus part of guest molecule and nearest methylene moiety penetrates in the cavity of copolymerization post 5 aromatic hydrocarbons, when mol ratio continues to increase to 1:2, these peak values are basically unchanged, and illustrate that Subjective and Objective molecule is the mol ratio complexing of 1:2.Post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex in aqueous highly stable, long-time placement does not interferes with its detection performance.
Two, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is in the application of detection iron ion
1, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex fluorescence response to iron ion
Being dissolved in water by post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, being configured to main body concentration is 1 × 10-5The aqueous solution of mol/L.Pipetting 0.5mL respectively in a series of 10 mL colorimetric cylinders, this solution sends yellow fluorescence under uviol lamp.The Fe of 16 times of equivalents it is separately added in colorimetric cylinder3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+, Eu3+, Tb3+, La3+Plasma, measures the fluorescence intensity change of solution.As it is shown on figure 3, only Fe3+Addition solution can be made by strong yellow fluorescence quencher, and the fluorescence on solution that adds of other cation does not produce impact (yellow fluorescence not quencher).Illustrate that this host-guest coordination compound can carry out narrow spectrum fluorescence identifying to iron ion, therefore can realize iron ion in water body is implemented the detection of spectroscopy by this pattern.
2, fluorescence titration experiment
For the further test pole 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex fluorescence intensity change to addition iron ion, we have done fluorescence titration experiment.Fig. 4 is copolymerization post 5 aromatic hydrocarbons and the guest molecule fluorescence titration figure to iron ion.It is 1 × 10 in complex concentration-5Adding iron ion in the aqueous solution of mol/L, not adding fashionable has the strongest fluorescence emission peak, and along with the increase of iron molecule concentration, fluorescence intensity gradually weakens, and finally reaches fluorescent quenching.This weakening is owing to the guest molecule 2-hydroxyl-3-naphthoic acid of electron deficient system penetrates in the cavity of copolymerization post 5 aromatic hydrocarbons of electron rich system, make electro transfer cause host molecule fluorescent quenching, also demonstrate that equally in the cavity that 2-hydroxyl-3-naphthoic acid moieties inclusion has arrived copolymerization post 5 aromatic hydrocarbons.Titration experiments shows, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is limited to 8.328 × 10 to the detection adding iron ion-7。
3, to iron ion, the fluorescence response of fluorine ion continuity identification
Being dissolved in water by post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, being configured to main body concentration is 1 × 10-5The aqueous solution of mol/L, is subsequently adding the iron ion of 16 times of equivalents.Pipette 0.5mL respectively in a series of 10 mL colorimetric cylinders, and add the different anions (F of 2 times of equivalents-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -, SCN-, CN-, N3 -After), under uviol lamp, observe the fluorescence intensity change of solution.As it is shown in figure 5, only fluorine ion can make the fluorescence of solution revert to yellow.And adding of other anion does not produces impact (yellow fluorescence quencher) to solution.Illustrate post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex adds the specific recognition to fluorine ion after iron ion.
4, fluorine ion fluorescence titration experiment
Adding the fluorescence response of mixed liquor after iron ion to test fluorine ion coupled columns 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex further, we have done fluorescence titration experiment.As shown in Figure 6, it is 1 × 10 in main body concentration-5The aqueous solution of mol/L adds fluorescent quenching after iron ion.Then being gradually added into fluorine ion, along with the increase of fluorinion concentration, fluorescence intensity gradually strengthens, and finally reaches fluorescence and opens.Occur this phenomenon be primarily due to add after fluorine ion, fluorine ion and iron ion define complex, iron ion is caused to separate from the cavity of copolymerization post 5 aromatic hydrocarbons, thus cause complex molecule fluorescence to reopen, also demonstrate that equally in the cavity that 2-hydroxyl-3-naphthoic acid moieties inclusion has arrived copolymerization post 5 aromatic hydrocarbons.Titration experiments shows, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is limited to 8.328 × 10 to the detection of iron ion-7。
In sum, the present invention is based on copolymerization post 5 aromatic hydrocarbons, 2-hydroxyl-3-naphthoic acid is object, self assembly is passed through for driving force with C-H π and electrostatic attraction, by the part 2-hydroxyl-3-naphthoic acid inclusion with negative electrical charge in the cavity of post aromatic hydrocarbons under alkaline environment, thus complete Subjective and Objective assembling process, form more stable post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex.Subjective and Objective fluorescent quenching is made after adding iron ion；After continuously adding fluorine ion, fluorine ion and iron ion define complex, cause iron ion to separate from the cavity of copolymerization post 5 aromatic hydrocarbons, thus cause complex molecule fluorescence to reopen.Therefore, Fe can be measured by post 5 aromatic hydrocarbons 2-hydroxyl-3-naphthoic acid complex3+, F can be identified continuously by the fluorescent quenching of solution again-。
Accompanying drawing explanation
Fig. 1 is the one-dimensional nuclear-magnetism titration collection of illustrative plates of post 5 aromatic hydrocarbons and 2-hydroxyl-3-naphthoic acid self assembly.
Fig. 2 is the concentration nuclear-magnetism titration figure of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex.
Fig. 3 is post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex figure to iron ion specific recognition.
Fig. 4 is post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex fluorescence titration figure to iron ion.
Fig. 5 is to add after iron ion the specific recognition figure to fluorine ion in post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex.
Fig. 6 is to add after iron ion the fluorescence titration figure to fluorine ion in copolymerization post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex.
Detailed description of the invention
Below by the specific embodiment structure to post 5 aromatic hydrocarbons of the present invention/2-hydroxyl-3-naphthoic acid complex, synthesis, and for detecting iron ion in aqueous phase, the application of fluorine ion is described further.
One, the synthesis of copolymerization post 5 aromatic hydrocarbons
The synthesis of intermediate: by hydroquinones (2.2 g, 20.0 mmol), K2CO3
(13.8 g, 100 mmol), KI (0.83 g, 5mmol), Isosorbide-5-Nitrae dibromobutane alkane (17.28 g, 80mmol) join in 500mL round-bottomed flask with acetone (300.0mL), stirring 3 days (72h) of reaction, solid separates out, obtains intermediate 1.1H NMR (400MHz, CDCl3)
δ(ppm): δ 6.81 (s, 4H), 3.94 (dd,J =
10.0, 5.8 Hz, 4H), 3.48 (t,J = 6.6 Hz, 2H), 3.26 (t,J = 6.8 Hz,
2H), 2.09-1.85 (m, 8H).Productivity is 80%.
The synthesis of intermediate 2: intermediate (3.8 g, 10.0mmol) is joined in 80mL1,2 dichloroethanes and dissolve；Again paraformaldehyde (0.686 g, 20.0mmol), BFEE (0.686 g, 20.0mmol) are joined in solution, be stirred at room temperature reaction 20min.Solution is poured in distilled water after terminating by reaction, washs three times with distilled water, adds Na2SO4Being dried, filter, with silica gel mixed sample, organic phase, with pillar layer separation (petroleum ether/dichloromethane=1:1 v/v), obtains white solid, for intermediate 2.Productivity 40%.1H NMR (400 MHz, CDCl3)
δ(ppm): 6.82 (s, 10H), 3.94
(s, 20H), 3.75 (s, 10H), 3.45 (s, 10H), 3.25 (s, 10H), 2.00 (d,J = 47.7
Hz, 41H)。
The synthesis of copolymerization post 5 aromatic hydrocarbons: the intermediate that will obtain2 (1.00 g, 0.51mmol), trimethylamine (33 % in ethanol, 6.89 mL,
25.5mmol) adding in the ethanol solution of 50ml, back flow reaction 12h, then rotation is evaporated off ethanol, and the product revolved adds the distilled water of 20ml, adds acetonitrile continuation rotation and steams until there being white solid to produce, copolymerization post 5 aromatic hydrocarbons P i.e..Productivity 90%.1H NMR (400 MHz, D2O)
δ (ppm): 6.73 (s, 10H),
3.79 (s, 31H), 3.09 (s, 21H), 2.90 (s, 93H), 1.54 (s, 41H)。
The synthesis type of copolymerization post 5 aromatic hydrocarbons is as follows:
。
Two, the preparation of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex
By post 5 aromatic hydrocarbons (P), 2-hydroxyl-3-naphthoic acid, NaOH is dissolved in the water with the mol ratio of 1:2:2, and 1 min is stirred at room temperature, and obtains post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex aqueous solution.Post 5 aromatic hydrocarbons and 2-hydroxyl-3-naphthoic acid are self-assembly of the process of host-guest complex under alkaline environment and see Fig. 1.
Three, post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex detection aqueous phase in iron ion, the application of fluorine ion
Alkaline aqueous solution (concentration 1 × 10 at post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex-5Mol/L), in, it is separately added into Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+, Eu3+, Tb3+, La3+Solution, if the yellow fluorescence quencher of solution, then that add is Fe3+, otherwise add is other cationic solution.
Fe is added in the alkaline aqueous solution of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex3+, the yellow fluorescence quencher of solution；F it is separately added into again in the solution of fluorescent quenching-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -, SCN-, CN-, N3 -If the yellow fluorescence of solution is opened, then that add is F-, otherwise add is other anion solutions.
Claims (8)
1. post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, it is characterised in that: the naphthalene nucleus part of 2-hydroxyl-3-naphthoic acid penetrates into and reaches the inclusion of Subjective and Objective in the cavity of post 5 aromatic hydrocarbons and form complex.
2. post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex as claimed in claim 1, it is characterised in that: post 5 aromatic hydrocarbons and 2-hydroxyl-3-naphthoic acid carry out inclusion with the mol ratio of 1:2.
3. the synthetic method of as claimed in claim 1 post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, is by post 5 aromatic hydrocarbons, and 2-hydroxyl-3-naphthoic acid is dissolved in the water, and adds NaOH, it is stirred at room temperature 1 ~, 3min, obtain post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex aqueous solution.
4. the synthetic method of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex as claimed in claim 3, it is characterised in that: post 5 aromatic hydrocarbons is 1:2 with the mol ratio of 2-hydroxyl-3-naphthoic acid.
5. the synthetic method of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex as claimed in claim 3, it is characterised in that: 2-hydroxyl-3-naphthoic acid is 1:1 with the mol ratio of NaOH.
6. the iron ion during post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is used for fluoroscopic examination aqueous phase as claimed in claim 1.
7. the iron ion during post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is used for fluoroscopic examination aqueous phase as claimed in claim 6, it is characterised in that: in the alkaline aqueous solution of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, it is separately added into Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+, Eu3+, Tb3+, La3+Solution, only Fe3+Addition make the yellow fluorescence quencher of solution, and the fluorescence on solution that adds of other cationic solution does not affect.
8. the fluorine ion during post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex is used for fluoroscopic examination aqueous phase as claimed in claim 1, it is characterised in that: in the alkaline aqueous solution of post 5 aromatic hydrocarbons/2-hydroxyl-3-naphthoic acid complex, add Fe3+, the yellow fluorescence quencher of solution；F it is separately added into again in the solution of fluorescent quenching-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -, SCN-, CN-, N3 -, only F-Addition the yellow fluorescence of solution can be made to open.
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| CN110105947A (en) * | 2019-05-16 | 2019-08-09 | 西北师范大学 | The synthesis and application of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes |
| CN110441279A (en) * | 2019-08-29 | 2019-11-12 | 云南民族大学 | A kind of application of phosphonic acids column [5] aromatic hydrocarbons in identification ferrous ion, copper ion or aluminium ion |
| CN111057034A (en) * | 2019-12-02 | 2020-04-24 | 西北师范大学 | Coumarin functionalized pillared [5] arene and synthesis and application thereof |
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