CN104496846A - Preparation method of water-soluble fluorescent probe for specifically recognizing aluminum ions and application of water-soluble fluorescent probe - Google Patents
Preparation method of water-soluble fluorescent probe for specifically recognizing aluminum ions and application of water-soluble fluorescent probe Download PDFInfo
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Abstract
Disclosed is a preparation method of a water-soluble fluorescent probe for specifically recognizing aluminum ions. The compound name of the fluorescent probe is 2-hydroxy-1-[4'-N-((2-ethoxy) ethanol) methyl amino benzoyl] methyl naphthalene, the chemical formula of the fluorescent probe is C23H25N3O4, and the molecular structural formula of the fluorescent probe is shown in the specification. The preparation method includes the steps: forming Schiff base by taking methyl p-formylbenzoate and diglycolamine as raw materials; forming 4-N-[(2-ethoxy) ethanol dimethyl amino] benzoyl hydrazine by aid of reduction reaction and hydrazinolysis, and reacting the 4-N-[(2-ethoxy) ethanol dimethyl amino] benzoyl hydrazine with 2-hydroxy-1-naphthaldehyde to form a target compound. The preparation method has the advantages that the preparation method is simple in process and easy to implement and has an important application value for rapidly detecting the aluminum ions in water solution, raw materials are easily obtained, the prepared fluorescent probe has high selectivity for Al3+, and high-sensitivity detection for the aluminum ions is realized.
Description
Technical field
The present invention relates to fluorescent probe field, specifically about preparation method and the application thereof of the aluminum ions water-soluble fluorescent probe of a kind of specific recognition.
Background technology
Aluminium is a kind of metallic element that content is the highest in the earth's crust, it is one of rich secondary element of composition litre geosphere and soil mineral, mainly exist with the alumina form of insoluble, be widely used in aerospace, chemical metallurgy, automotive industry, agriculture production and daily life.But in the last few years, we had more and more recognized A1
3+the central nervous system of ion pair human body has very large physiological-toxicity.
The central nervous system of aluminum ion to human body has very large hazardness, and E.Altschuler reports: the medicine containing the anti-hydrochloric acid in gastric juice of aluminium can cause Primary ventricular hemorrhage, and has found a large amount of aluminium element from the Parkinsonian patient's hippocampal neural of trouble; The people such as S.Polizzi, by having carried out large quantifier elimination to senile dementia Disease and the workman that coins, find that aluminum ion has very strong neurotoxicity effect; The people such as B.Wang also find: if Long Term Contact aluminum products will have influence on man memory power by the conduction of multi-signal, make the decline that memory occurs in various degree; In addition, aluminum ion also can produce the harm of biological metabolism, has been reported and shows that aluminum ion can have influence on absorbing of calcium and selenium in organism.Meanwhile, aluminum ions toxicity is in acid condition than much bigger time in neutral conditions, and its reason is in acid condition, and the solvability of aluminium ore material is many greatly, thus adds aluminum ions concentration and activity.There are some researches show, aluminum ion toxicity when pH is about 5 is maximum, and in acid soil, aluminum ion can cause the underproduction of a large amount of farm crop, and suppresses root growth and the growth of plant; In addition, aluminum ion also can significantly affect growing of fresh-water fishes.Therefore, the high-sensitivity detection Al of highly selective is worked out
3+the probe of ion has great importance.
acylhydrazone has unique constitutional features: 1) containing multiple donor atom participating in coordination, thus coordination ability is very strong; 2) with heteroatomss such as nitrogen, oxygen and sulphur for ligating atom, similar to coenocorrelation; 3) there is larger π-conjugated systems in molecule, be expected that there is larger SHG (second harmonic generation) coefficient.There are keto-acid and these two kinds of tautomers of enol form in acylhydrazone, and again can with the form of monodentate or bidentate and the coordination of the many kinds of metal ions such as transition metal, rare earth metal, make it analysis, catalysis, optical material particularly biochemical field there is actual application prospect.Acylhydrazone often shows the biological activity being better than part after forming title complex.Therefore, the research of acylhydrazone and acylhydrazone class title complex becomes the important topic that chemist and biochemists study.
analyze in conjunction with above, the present invention's design, a kind of small-molecule fluorescent probe synthesized, can be applied to Al
3+
analyzing and testing.This fluorescent molecular probe molecule has the features such as highly sensitive, selectivity good, testing cost is low, for detecting Al in organism
3+
the further research of fluorescent probe indicate a direction.
Summary of the invention
The object of the invention is for above-mentioned existing problems, preparation method and the application thereof of the aluminum ions water-soluble fluorescent probe of specific recognition that a kind of selectivity is high and sensitivity is good are provided.
Technical scheme of the present invention:
The preparation method of the aluminum ions water-soluble fluorescent probe of a kind of specific recognition; the compound name of described fluorescent probe is called 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene, and chemical molecular formula is C
23h
25n
3o
4, molecular structural formula is:
Preparation process is as follows:
1) p formylbenzoic acid methyl esters and diglycolamine are added in dehydrated alcohol, after stirred at ambient temperature 5 h, sodium triacetoxy borohydride being divided equally three times joins in reaction system, TLC detection reaction process, after question response is complete, add distilled water, with dichloromethane extraction, after concentrated, drying, obtain oily compound 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate;
2) hydrazine hydrate of above-mentioned 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate and 80wt% is added in dehydrated alcohol, back flow reaction 24 h, screw out ethanol, column chromatography purified product, obtains compound 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine;
3) by above-mentioned 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine and the mixing of 2-hydroxyl-1-naphthalene Formaldehyde; after adding anhydrous alcohol solution; stirred at ambient temperature 5h; then column chromatography purifying crude product, obtains yellowish brown compound 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene.
The mass ratio of described p formylbenzoic acid methyl esters, diglycolamine, sodium triacetoxy borohydride and dehydrated alcohol is 1:2:4:12; The mass ratio of sodium triacetoxy borohydride and distilled water is 3:4.5-5.5.
Described 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate, the hydrazine hydrate of 80wt% and the mass ratio of dehydrated alcohol are 1:1.9:15.
The mass ratio of described 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine, 2-hydroxyl-1-naphthalene Formaldehyde and dehydrated alcohol is 1:1.4:90.
An application for the prepared aluminum ions water-soluble fluorescent probe of specific recognition, as the aluminum ions water-soluble fluorescent probe of rapid detection metal.
Fluorescent probe prepared by the method has good fluorescence property to metallic aluminium ion, can make ultra-violet absorption spectrum generation red shift, fluorescence intensity strengthens greatly in aqueous optionally in conjunction with metallic aluminium ion.
Advantage of the present invention is: this preparation method's technique is simple, raw material is easy to get, easy to implement, and the fluorescent probe of preparation has higher selectivity to metallic aluminium ion, achieves aluminum ions high-sensitivity detection, has important using value.
Accompanying drawing explanation
For this probe aqueous solution, (concentration is 1 × 10 to Fig. 1
-5and Al mol/L)
3+uv-absorbing variation diagram after reaction.
For this probe aqueous solution, (concentration is 1 × 10 to Fig. 2
-5and Al mol/L)
3+the variation diagram of fluorescence emission spectrum after reaction.
For this probe aqueous solution, (concentration is 1 × 10 to Fig. 3
-5mol/L) with the different metal ion (Sn of same concentrations
2+, Cd
2+, Al
3+, Mn
2+, K
+, Na
+, Mg
2+, Cu
2+, Ca
2+, Zn
2+, Fe
3+, Hg
2+, Pd
2+, Co
2+) the rear uv-absorbing variation diagram of reaction.
For this probe aqueous solution, (concentration is 1 × 10 to Fig. 4
-5and Al mol/L)
3+the mensuration figure of reacted lowest detection line.
For this probe aqueous solution, (concentration is 1 × 10 to Fig. 5
-5) and Al mol/L)
3+the mensuration figure of reacted binding constant.
Embodiment
Below by the present invention of embodiment specific description, but the present invention is not by the restriction of following embodiment.
embodiment:
The preparation method of the aluminum ions water-soluble fluorescent probe of a kind of specific recognition; the compound name of described fluorescent probe is called 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene, and chemical molecular formula is C
23h
25n
3o
4, molecular structural formula is:
，
Preparation process is as follows:
1) 1.64 g p formylbenzoic acid methyl esters and 3.28 g diglycolamines are added in 25 mL dehydrated alcohols; after stirred at ambient temperature 5 h; 6.55 g sodium triacetoxy borohydrides are divided equally three times to be joined in reaction system; TLC detection reaction process; question response completely after, add 10 g distilled water, after dichloromethane extraction, concentrated, drying; obtain 1.21 g oily compound 4-N – [(2-oxyethyl group) ethanol methylamino-] methyl benzoate (I), productive rate 47.8%.
1H NMR (400MHz, CDCl
3): δ (ppm) = 8.02 (d, J = 8.4 Hz, 2H, Ar-H), 7.42 (d, J = 8.4 Hz, 2H, Ar-H), 3.93 (s, 3H, -CH
3), 3.90 (s, 2H, -CH
2-), 3.75 (t, J = 4Hz, 2H, -CH2-), 3.66 (t, J = 5.2 Hz, -CH2-), 3.61 (t, J = 4.8 Hz, -CH2-), 2.85 (t, J = 5.2 Hz, -CH2-), 2.22 (s, 2H, -NH-, -OH),Analytically calculated for C
13H
19NO
4：C, 61.64; H, 7.56; N, 5.53%. Found: C, 61.54 ; H, 7.67; N, 5.56%。
Reaction formula is:
。
2) hydrazine hydrate of above-mentioned 0.76 g4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate and 1.47 g 80wt% is added in 15 mL dehydrated alcohols, back flow reaction 24 h, screw out ethanol, column chromatography purified product, obtain 0.68 g compound 4-N – [(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine (II), productive rate 87.2%.
1H NMR (400MHz, CDCl
3): δ (ppm) = 7.70 (d, J = 8.4 Hz , 2H, Ar-H), 7.41 (d, J = 8.4 Hz, 2H, Ar-H), 7.34 (s, 1H, -NH-), 3.87 (s, 2H, -CH
2-), 3.73 (t, J = 4 Hz, 2H, -CH
2-), 3.64 (t, J = 5.2 Hz, -CH
2-), 3.59 (t, J = 4.8 Hz, -CH
2-), 2.82 (t, J = 5.2 Hz, -CH
2-), Analytically calculated for C
12H
19N
3O
3: C, 56.90; H, 7.56; N, 16.59%. Found: C, 56.85 ; H, 7.64 ; N, 16.46%。
Reaction formula is:
。
3) by above-mentioned 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine and the mixing of 2-hydroxyl-1-naphthalene Formaldehyde; after adding anhydrous alcohol solution; stirred at ambient temperature 5h; then column chromatography purifying crude product, obtains yellowish brown compound 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene.
3) by the above-mentioned 4-N-of 0.13 g [(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine and 0.18 g 2-hydroxyl-1-naphthalene Formaldehyde in 50 mL round-bottomed flasks, after adding 15 mL anhydrous alcohol solutions, stirred at ambient temperature 5h, stopped reaction, column chromatography purifying crude product, obtain yellowish brown compound 0.08g, productive rate: 40%
1h NMR (400 MHz, DMSO): δ (ppm)=9.55 (s, 1H ,-C
h=N-), 8.23 (d, 1H, J=8.9 Hz, Ar-
h), 7.98 (d, 2H, J=8.0 Hz, Ar-
h), 7.91 (m, 2H, Ar-
h), 7.63 (t, 1H, J=7.2 Hz, Ar-
h), 7.56 (d, 2H, J=8.0 Hz, Ar-
h), 7.42 (t, 1H, J=7.2 Hz, Ar-
h), 7.25 (d, 1H, J=8.9 Hz, Ar-
h), 3.87 (s, 2H, Ph-C
h 2 -NH), 3.51 (m, 4H ,-C
h 2 -O-C
h 2 -), 3.43 (m, 2H ,-CH
2-OH), 2.72 (m, 2H ,-NH-C
h 2 -);
13c NMR (100 MHz, DMSO-d
6): δ (ppm)=162.78,158.47,147.25,147.22,133.18,129.45,128.80,128.34,128.27,128.22,128.05,124.01,121.07,119.40,109.01,72.66,69.73,60.70,52.52,48.31. Analytically calculated for C
23h
25n
3o
4: C, 67.98; H, 6.13; N, 10.56 %. Found:C, 67.80; H, 6.18; N, 10.31 %. ESI-MS:m/z:calcd:408.1935, found:408.1923 [M+1].
Reaction formula is:
。
The prepared aluminum ions water-soluble fluorescent probe of specific recognition, as the aluminum ions water-soluble fluorescent probe of rapid detection metal.
The spectrum test of fluorescent probe:
By soluble in water for the fluorescent probe of preparation, being mixed with concentration is 1 × 10
-5the aqueous solution of mol/L, detects its spectrum property.
Fig. 1 is the Al adding different concns to this probe aqueous solution gradually
3+solution, measures the change of ultraviolet spectra for titration, can find out: maximum absorption wavelength is 364 nm in Fig. 1, constantly increase the Al of different concns
3+after the aqueous solution, ultra-violet absorption spectrum red shift 38 nm.
Fig. 2 is the Al adding different concns to this probe aqueous solution gradually
3+solution, excitation wavelength 364 nm of setting, slit width is the fluorescence intensity change spectrum of 1.0,2.5 nm, mensuration, shows in figure: the emission wavelength of probe is 474 nm, in solution, constantly add Al
3+after the aqueous solution, the fluorescence intensity of this compound strengthens gradually.
Fig. 3 is the metal ion Sn of same concentrations
2+, Cd
2+, Al
3+, Mn
2+, K
+, Na
+, Mg
2+, Cu
2+, Ca
2+, Zn
2+, Fe
3+, Hg
2+, Pd
2+, Co
2+fluorescence intensity change collection of illustrative plates reacted with fluorescent probe, as can be seen from the figure, except Al
3+make outside fluorescence intensity enhancing, the fluorescence intensity of other metal ions to this compound added all has no significant effect, and can illustrate that this compound is to Al
3+there is very high selectivity.
Fig. 4 is the linear relationship chart of fluorescent probe and metallic aluminium ionic reaction, can obtain this probe to Al by figure
3+lowest detection line be 0.165 μm of o1/L.
Fig. 5 is the linear relationship chart of the fluorometric titration that this probe and aluminum ion react, and can be calculated and aluminum ions binding constant and Ks=8.40 × 10 by figure
4l/mol.
Claims (5)
1. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition; it is characterized in that: the compound name of described fluorescent probe is called 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene, and chemical molecular formula is C
23h
25n
3o
4, molecular structural formula is:
，
Preparation process is as follows:
1) p formylbenzoic acid methyl esters and diglycolamine are added in dehydrated alcohol, after stirred at ambient temperature 5 h, sodium triacetoxy borohydride being divided equally three times joins in reaction system, TLC detection reaction process, after question response is complete, add distilled water, with dichloromethane extraction, after concentrated, drying, obtain oily compound 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate;
2) hydrazine hydrate of above-mentioned 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate and 80wt% is added in dehydrated alcohol, back flow reaction 24 h, screw out ethanol, column chromatography purified product, obtains compound 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine;
3) by above-mentioned 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine and the mixing of 2-hydroxyl-1-naphthalene Formaldehyde; after adding anhydrous alcohol solution; stirred at ambient temperature 5h; then column chromatography purifying crude product, obtains yellowish brown compound 2-hydroxyl-1-[4'-N-((2-oxyethyl group) ethanol) methylamino benzoyl] methylnaphthalene.
2. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition according to claim 1, is characterized in that: the mass ratio of described p formylbenzoic acid methyl esters, diglycolamine, sodium triacetoxy borohydride and dehydrated alcohol is 1:2:4:12; The mass ratio of sodium triacetoxy borohydride and distilled water is 3:4.5-5.5.
3. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition according to claim 1, is characterized in that: described 4-N-[(2-oxyethyl group) ethanol methylamino-] methyl benzoate, the hydrazine hydrate of 80wt% and the mass ratio of dehydrated alcohol are 1:1.9:15.
4. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition according to claim 1, it is characterized in that: 2. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition according to claim 1, is characterized in that: the mass ratio of described 4-N-[(2-oxyethyl group) ethanol methylamino-] benzoyl hydrazine, 2-hydroxyl-1-naphthalene Formaldehyde and dehydrated alcohol is 1:1.4:90.
5. an application for the aluminum ions water-soluble fluorescent probe of the specific recognition prepared by claim 1, is characterized in that: as the aluminum ions water-soluble fluorescent probe of rapid detection metal.
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| CN105092505A (en) * | 2015-06-08 | 2015-11-25 | 盐城师范学院 | Method for rapid detection of metal Al<3+> |
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| CN107474824A (en) * | 2016-06-07 | 2017-12-15 | 天津医科大学 | Aluminium ion fluorescence probe |
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