CN104496846B - The preparation method and applications of the aluminum ions water-soluble fluorescent probe of specific recognition - Google Patents
The preparation method and applications of the aluminum ions water-soluble fluorescent probe of specific recognition Download PDFInfo
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Abstract
A kind of preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition; the compound name of described fluorescent probe is 2 hydroxyl 1 [4'N ((2 ethyoxyl) ethanol) methylamino benzoyl] methyl naphthalenes, and chemical molecular formula is C23H25N3O4, molecular structural formula is:Preparation method is: forming Schiff's base for raw material occurring the reaction of reduction reaction, hydrazinolysis to form 4 N [(2 ethyoxyl) ethanol methylamino] benzoyl hydrazine with p formylbenzoic acid methyl ester, diglycolamine, it reacts formation target compound with 2 hydroxyl 1 naphthaldehydes.The invention have the advantage that this preparation method technique is simple, raw material is easy to get, easy to implement, the fluorescent probe of preparation is to Al3+There is higher selectivity, it is achieved that to aluminum ions high-sensitivity detection, the most quickly detection metallic aluminium ion is had important using value.
Description
Technical field
The present invention relates to fluorescent probe field, specifically about a kind of aluminum ions water-soluble fluorescent probe of specific recognition
Preparation method and applications.
Background technology
Aluminum is a kind of metallic element that content is the highest in the earth's crust, be composition lithosphere and soil mineral rich secondary element it
One, mainly exist with the alumina form of slightly solubility, be widely used in Aero-Space, chemical metallurgy, auto industry, agricultural life
Produce and in daily life.But in the last few years, we have more and more recognized A13+The central nervous system of ion pair human body
System has the biggest physiological-toxicity.
Aluminium ion has the biggest hazardness to the central nervous system of human body, and E.Altschuler reports: containing aluminum
The medicine of anti-gastric acid can result in Primary ventricular hemorrhage, and also be found that from suffering from Parkinsonian patient's hippocampal neural
A large amount of aluminium elements；S.Polizzi et al., by senile dementia Disease and the workman that coins have been carried out substantial amounts of research, finds
Aluminium ion has the strongest neurotoxicity effect；B.Wang et al. it has also been found that: if Long Term Contact aluminum products will pass through multiple letter
Number conduction thus have influence on man memory power, make memory that decline in various degree to occur；Additionally, aluminium ion also can produce life
The harm of thing metabolic, has been reported and shows that aluminium ion influences whether absorbing of calcium and selenium in organism.Meanwhile, aluminum
The toxicity of ion is more much bigger than time in neutral conditions in acid condition, and its reason is in acid condition, aluminium ore material
Dissolubility want big many, thus add aluminum ions concentration and activity.There are some researches show, aluminium ion is about 5 at pH
Time toxicity be maximum, and in acid ground, aluminium ion can result in the underproduction of a large amount of crops, and suppresses plant
Root growth and growth；In addition, aluminium ion also can significantly affect the growth promoter of fresh-water fishes.Therefore, work out Gao Xuan
High-sensitivity detection Al of selecting property3+The probe of ion has great importance.
Acylhydrazone has an architectural feature of uniqueness: 1) containing multiple donor atoms that may participate in coordination, thus join
Capability is the strongest；2) with hetero atoms such as nitrogen, oxygen and sulfur as coordination atom, similar to biotic environment；3) molecule exists bigger
π-conjugated systems, it is expected to there is bigger SHG (second harmonic generation) coefficient.There is ketone in acylhydrazone
Formula and enol form both tautomers, and again can be with the form of monodentate or bidentate and transition metal, rare earth metal
It is coordinated Deng many kinds of metal ions so that it is before analysis, catalysis, optical material particularly biochemical field have actual application
Scape.Acylhydrazone often shows, after forming coordination compound, the biological activity being better than part.Therefore, acylhydrazone and acylhydrazone class coordinate
The important topic that the research of thing becomes chemist and biochemists are studied.
Analyze in conjunction with above, present invention design, a kind of small-molecule fluorescent probe synthesized, Al can be applied to3+'s
Analyze detection.This fluorescent molecular probe molecule has the features such as highly sensitive, selectivity good, testing cost is low, in organism
Detection Al3+The further research of fluorescent probe indicate a direction.
Summary of the invention
It is an object of the invention to for above-mentioned existing problems, it is provided that the specific recognition that a kind of selectivity is high and sensitivity is good
The preparation method and applications of aluminum ions water-soluble fluorescent probe.
Technical scheme:
A kind of preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition, the chemical combination name of described fluorescent probe
Being referred to as 2-hydroxyl-1-[4'-N-((2-ethyoxyl) ethanol) methylamino benzoyl] methyl naphthalene, chemical molecular formula is
C23H25N3O4, molecular structural formula is:
Preparation process is as follows:
1) p formylbenzoic acid methyl ester and diglycolamine are added in dehydrated alcohol, after stirring 5 h under room temperature, by three
Acetoxyl group sodium borohydride joins in reaction system the most in three times, and TLC detects reaction process, after question response is complete, adds and steams
Distilled water, extracts with dichloromethane, concentrates, dried, obtains oily compound 4-N-[(2-ethyoxyl) ethanol methylamino] benzene first
Acid methyl ester；
2) hydrazine hydrate of above-mentioned 4-N-[(2-ethyoxyl) ethanol methylamino] essence of Niobe and 80wt% is added anhydrous second
In alcohol, back flow reaction 24 h, screw out ethanol, column chromatography purified product, obtain compound 4-N-[(2-ethyoxyl) ethanol methylamino]
Benzoyl hydrazine；
3) above-mentioned 4-N-[(2-ethyoxyl) ethanol methylamino] benzoyl hydrazine and 2-hydroxyl-1-naphthalene Formaldehyde are mixed, add
After anhydrous alcohol solution, stir 5h, then column chromatography purifying crude product under room temperature, obtain yellowish-brown compound 2-hydroxyl-1-[4'-
N-((2-ethyoxyl) ethanol) methylamino benzoyl] methyl naphthalene.
Described p formylbenzoic acid methyl ester, diglycolamine, sodium triacetoxy borohydride and the mass ratio of dehydrated alcohol
For 1:2:4:12；Sodium triacetoxy borohydride is 3:4.5-5.5 with the mass ratio of distilled water.
Described 4-N-[(2-ethyoxyl) ethanol methylamino] essence of Niobe, the hydrazine hydrate of 80wt% and the matter of dehydrated alcohol
Amount ratio is 1:1.9:15.
Described 4-N-[(2-ethyoxyl) ethanol methylamino] benzoyl hydrazine, 2-hydroxyl-1-naphthalene Formaldehyde and the matter of dehydrated alcohol
Amount ratio is 1:1.4:90.
The application of a kind of prepared aluminum ions water-soluble fluorescent probe of specific recognition, is used as quickly to detect metallic aluminium
The water-soluble fluorescent probe of ion.
Fluorescent probe prepared by the method has good fluorescence property to metallic aluminium ion, can select in aqueous
The combination metallic aluminium ion of property, makes ultra-violet absorption spectrum generation red shift, fluorescence intensity be greatly enhanced.
The invention have the advantage that this preparation method technique is simple, raw material is easy to get, easy to implement, the fluorescent probe pair of preparation
Metallic aluminium ion has higher selectivity, it is achieved that to aluminum ions high-sensitivity detection, have important using value.
Accompanying drawing explanation
Fig. 1 is that (concentration is 1 × 10 to this probe aqueous solution-5And Al mol/L)3+Uv absorption variation diagram after reaction.
Fig. 2 is that (concentration is 1 × 10 to this probe aqueous solution-5And Al mol/L)3+The change of fluorescence emission spectrum after reaction
Figure.
Fig. 3 is that (concentration is 1 × 10 to this probe aqueous solution-5Mol/L) with the different metal ion (Sn of same concentrations2+、Cd2
+、Al3+ 、Mn2+、 K+、 Na+ 、Mg2+ 、Cu2+ 、Ca2+、 Zn2+ 、Fe3+ 、Hg2+、 Pd2+、 Co2+) uv absorption after reaction
Variation diagram.
Fig. 4 is that (concentration is 1 × 10 to this probe aqueous solution-5And Al mol/L)3+The mensuration of reacted lowest detection line
Figure.
Fig. 5 is that (concentration is 1 × 10 to this probe aqueous solution-5) and Al mol/L)3+The mensuration of reacted binding constant
Figure.
Detailed description of the invention
Below by the embodiment specific description present invention, but the present invention is not limited by following embodiment.
Embodiment:
A kind of preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition, the chemical combination name of described fluorescent probe
Being referred to as 2-hydroxyl-1-[4'-N-((2-ethyoxyl) ethanol) methylamino benzoyl] methyl naphthalene, chemical molecular formula is
C23H25N3O4, molecular structural formula is:
,
Preparation process is as follows:
1) 1.64 g p formylbenzoic acid methyl ester and 3.28 g diglycolamines are added in 25 mL dehydrated alcohol, room temperature
After lower stirring 5 h, 6.55 g sodium triacetoxy borohydrides are joined in reaction system the most in three times, TLC detection react into
Journey, question response completely after, add 10 g distilled water, with dichloromethane extraction, concentrate, dried, obtain 1.21 g oily chemical combination
Thing 4-N [(2-ethyoxyl) ethanol methylamino] essence of Niobe (I), productivity 47.8%.1H NMR (400MHz, CDCl3):
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, -CH3), 3.90 (s, 2H, -CH2-), 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 C13H19NO4: C, 61.64;
H, 7.56; N, 5.53%. Found: C, 61.54 ; H, 7.67; N, 5.56%。
Reaction equation is:
。
2) by above-mentioned 0.76 g4-N-[(2-ethyoxyl) ethanol methylamino] essence of Niobe and the water of 1.47 g 80wt%
Close hydrazine and add in 15 mL dehydrated alcohol, back flow reaction 24 h, screw out ethanol, column chromatography purified product, obtain 0.68 g compound 4
-N [(2-ethyoxyl) ethanol methylamino] benzoyl hydrazine (II), productivity 87.2%.1H NMR (400MHz, CDCl3):
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, -CH2-), 3.73 (t, J = 4 Hz, 2H, -CH2-), 3.64
(t, J = 5.2 Hz, -CH2-), 3.59 (t, J = 4.8 Hz, -CH2-), 2.82 (t, J = 5.2 Hz, -
CH2-), Analytically calculated for C12H19N3O3: C, 56.90; H, 7.56; N, 16.59%.
Found: C, 56.85 ; H, 7.64 ; N, 16.46%。
Reaction equation is:
。
3) above-mentioned 4-N-[(2-ethyoxyl) ethanol methylamino] benzoyl hydrazine and 2-hydroxyl-1-naphthalene Formaldehyde are mixed, add
After anhydrous alcohol solution, stir 5h, then column chromatography purifying crude product under room temperature, obtain yellowish-brown compound 2-hydroxyl-1-[4'-
N-((2-ethyoxyl) ethanol) methylamino benzoyl] methyl naphthalene.
3) by the 0.13 above-mentioned 4-N-of g [(2-ethyoxyl) ethanol methylamino] benzoyl hydrazine and 0.18 g 2-hydroxyl-1-naphthalene
Formaldehyde is in 50 mL round-bottomed flasks, after adding 15 mL anhydrous alcohol solutions, stirs 5h under room temperature, and stopped reaction, column chromatography carries
Pure crude product, obtains yellowish-brown compound 0.08g, productivity: 40%,1H NMR (400 MHz, DMSO): δ (ppm) = 9.55
(s, 1H,-CH=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-CH2-NH), 3.51(m, 4H, -CH2-O-CH2-), 3.43(m, 2H, -CH2-OH), 2.72(m, 2H, -NH-
CH2-); 13C NMR (100 MHz, DMSO-d6): 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 C23H25N3O4 : 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 equation is:
。
The prepared aluminum ions water-soluble fluorescent probe of specific recognition, is used as quickly detection metal aluminum ions water-soluble
Property fluorescent probe.
The spectrum test of fluorescent probe:
By soluble in water for the fluorescent probe of preparation, being configured to concentration is 1 × 10-5The aqueous solution of mol/L, detects its spectrum
Performance.
Fig. 1 is the Al being gradually added into variable concentrations to this probe aqueous solution3+Solution, measures the change of ultraviolet spectra for titration, Fig. 1
In it can be seen that a length of 364 nm of maximum absorption wave, be continuously increased the Al of variable concentrations3+After aqueous solution, ultra-violet absorption spectrum is red
38 nm are moved.
Fig. 2 is the Al being gradually added into variable concentrations to this probe aqueous solution3+Solution, excitation wavelength 364 nm of setting, narrow
Seam width is 1.0,2.5 nm, and the fluorescence intensity change spectrum of mensuration shows in figure: a length of 474 nm of transmitted wave of probe, to
Solution is continuously added Al3+ After aqueous solution, the fluorescence intensity of this compound gradually strengthens.
Fig. 3 is the metal ion Sn of same concentrations2+、Cd2+、Al3+ 、Mn2+、 K+、 Na+ 、Mg2+ 、Cu2+ 、Ca2+、
Zn2+ 、Fe3+ 、Hg2+、 Pd2+、 Co2+Fluorescence intensity change collection of illustrative plates reacted with fluorescent probe, as can be seen from the figure, removes
Al3+Outside making fluorescence intensity strengthen, the fluorescence intensity of this compound is all had no significant effect by other metal ions of addition, permissible
Illustrate that this compound is to Al3+There is the highest selectivity.
Fig. 4 is the linear relationship chart of fluorescent probe and metallic aluminium ionic reaction, figure can obtain this probe to Al3+?
Low detection line is 0.165 μm o1/L.
Fig. 5 is the linear relationship chart of the fluorescence titration that this probe reacts with aluminium ion, figure can calculate with aluminum ions
Binding constant i.e. Ks=8.40 × 104 L/mol。
Claims (5)
1. the preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition, it is characterised in that: described fluorescent probe
Compound name be (E)-4-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino]-N-(1-methyl-2 hydroxy naphthalene) benzoyl
Hydrazine, chemical molecular formula is C23H25N3O4, molecular structural formula is:
Preparation process is as follows:
1) p formylbenzoic acid methyl ester and diglycolamine are added in dehydrated alcohol, after stirring 5h under room temperature, by triacetyl oxygen
Base sodium borohydride joins in reaction system the most in three times, and TLC detects reaction process, after question response is complete, adds distilled water, uses
Dichloromethane extracts, and concentrates, dried, obtains oily compound 4-N-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino] benzene first
Acid methyl ester；
2) hydrazine hydrate of above-mentioned 4-N-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino] essence of Niobe and 80wt% is added
In dehydrated alcohol, back flow reaction 24h, screw out ethanol, column chromatography purified product, obtain compound 4-N-[(2-(2-hydroxyl) ethoxy
Base) ethylmethylamino] benzoyl hydrazine；
3) above-mentioned 4-N-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino] benzoyl hydrazine and 2-hydroxyl-1-naphthalene Formaldehyde are mixed,
After adding anhydrous alcohol solution, stir 5h, then column chromatography purifying crude product under room temperature, obtain yellowish-brown compound (E)-4-[(2-
(2-hydroxyl) ethyoxyl) ethylmethylamino]-N-(1-methyl-2 hydroxy naphthalene) benzoyl hydrazine.
The preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition the most according to claim 1, it is characterised in that:
Described p formylbenzoic acid methyl ester, diglycolamine, sodium triacetoxy borohydride are 1:2:4 with the mass ratio of dehydrated alcohol:
12；Sodium triacetoxy borohydride is 3:4.5-5.5 with the mass ratio of distilled water.
The preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition the most according to claim 1, it is characterised in that:
Described 4-N-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino] essence of Niobe, the hydrazine hydrate of 80wt% and the matter of dehydrated alcohol
Amount ratio is 1:1.9:15.
The preparation method of the aluminum ions water-soluble fluorescent probe of specific recognition the most according to claim 1, it is characterised in that:
Described 4-N-[(2-(2-hydroxyl) ethyoxyl) ethylmethylamino] benzoyl hydrazine, 2-hydroxyl-1-naphthalene Formaldehyde and the matter of dehydrated alcohol
Amount ratio is 1:1.4:90.
5. the application of the aluminum ions water-soluble fluorescent probe of specific recognition prepared by a claim 1, it is characterised in that:
It is used as the quickly detection aluminum ions water-soluble fluorescent probe of 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+> |
| CN107474824A (en) * | 2016-06-07 | 2017-12-15 | 天津医科大学 | Aluminium ion fluorescence probe |
| CN107286056B (en) * | 2017-07-05 | 2019-07-19 | 安徽大学 | It is a kind of to contain daiamid-anthryl schiff bases fluorescent probe compounds and its preparation method and application |
| CN107748161B (en) * | 2017-08-23 | 2020-02-18 | 曲阜师范大学 | Method for distinguishing trace Fe2+ and Fe3+ by multi-wavelength colorimetry |
| CN108181279B (en) * | 2017-12-29 | 2020-11-03 | 湖北大学 | Detect Al3+Fluorescent polydopamine nanoparticle solution and preparation method thereof |
| CN108362669B (en) * | 2017-12-29 | 2020-12-18 | 湖北大学 | For detecting Al3+Organic fluorescent polydopamine nanoparticle solution and preparation method thereof |
| CN110511190A (en) * | 2019-08-12 | 2019-11-29 | 山西大学 | A kind of benzsulfamide thiazole schiff base compounds and its preparation method and application |
| CN111004154B (en) * | 2019-11-29 | 2022-01-11 | 华南师范大学 | (E) -benzyl 2- ((2-hydroxynaphthalene-1-yl) methylene) hydrazine benzyl formate and preparation method and application thereof |
| CN112552278A (en) * | 2020-12-11 | 2021-03-26 | 北京印刷学院 | Aluminum ion fluorescent probe and preparation method and application thereof |
| CN112724040B (en) * | 2021-01-08 | 2022-04-19 | 中国药科大学 | Cationic fluorescent probe based on tetraphenylethylene structure |
| CN113087651B (en) * | 2021-03-24 | 2023-03-10 | 华南师范大学 | Compound containing indole group and preparation method and application thereof |
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