CN109180705B - Fluorescent compound and preparation method and application thereof - Google Patents

Fluorescent compound and preparation method and application thereof Download PDF

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CN109180705B
CN109180705B CN201811125713.5A CN201811125713A CN109180705B CN 109180705 B CN109180705 B CN 109180705B CN 201811125713 A CN201811125713 A CN 201811125713A CN 109180705 B CN109180705 B CN 109180705B
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陈修文
邵佳新
杨志海
郭子茵
杨子萍
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Jiangmen Zhongtuo Testing Technology Co.,Ltd.
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Abstract

The invention discloses a fluorescent compound, the chemical name of which is 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine), and fluorescence property tests show that the compound can treat Hg2+High selectivity and sensitivity, good chemical stability and water solubility, and can be applied to the field of mercury ion detection. The invention also provides a synthetic method of the compound, which is particularly obtained by two-step synthesis by taking 2-amino-3-pyridylaldehyde and p-methoxypropiophenone as main raw materials.

Description

Fluorescent compound and preparation method and application thereof
Technical Field
The invention relates to the field of organic luminescent materials, in particular to a fluorescent compound, a preparation method thereof and application thereof in mercury ion detection.
Background
Mercury is a typical highly toxic heavy metal, and trace mercury can generate strong toxicity. In an aqueous environment, mercury ions tend to rapidly accumulate in the body of organisms such as fish in the form of methyl mercury and enter the food chain, eventually destroying the human nervous system and causing cognitive and motor disorders. The divalent mercury ion in a free state is a common form, and can cause serious harm to the central nerve of the human body and multiple enzymes of the human body. Due to the extreme toxicity of mercury ions, several countries and related organizations in the world place strict limits on the content of mercury ions in drinking water and food products. Meanwhile, the monitoring of the content of mercury ions in organisms and environments also becomes an important research field.
The fluorescent probe has the advantages of low cost, simple operation, low detection limit, real-time monitoring and the like, and is widely concerned in metal ion detection. The fluorescence-enhanced sensing material can reduce detection errors, can accurately detect a complex system, can simultaneously detect different analytes by using various detection objects, and gradually becomes a new means for detecting mercury ions in recent years. However, Hg reported so far2+Fluorescent chemical probes still suffer from some limitations in practical applications, such as: some have insufficient specificity and are easily interfered by other metal ions; some are difficult to synthesize and have complex structures; some membranes have poor permeability and the like. Therefore, there is still a lack of a method for detecting Hg with high sensitivity, good selectivity, and excellent performance and simultaneously realizing water phase detection2+A fluorescent chemical probe.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a pair of Hg2+The fluorescent compound has high selectivity and high sensitivity and can be used as a fluorescent probe to be applied to the field of mercury ion detection.
In order to achieve the purpose, the invention adopts the following technical scheme:
a fluorescent compound having the structure shown in formula (I):
Figure BDA0001812332320000011
the chemical name of the compound shown in the formula (I) is 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine).
The compound shown in the formula (I) is obtained by two-step synthesis by taking 2-amino-3-pyridylaldehyde (1a) and p-methoxypropiophenone (2a) as main raw materials, and the synthetic route is shown as follows:
Figure BDA0001812332320000021
wherein, in order to obtain the intermediate product 2- (4-methoxyphenyl) -3-methyl-1, 8-naphthyridine (3a) in the first step, a first solvent is also added.
The more specific synthesis method comprises the following steps:
s1, taking 2-amino-3-pyridylaldehyde and p-methoxypropiophenone, adding potassium tert-butoxide, dissolving with a first solvent, reacting at 25-80 ℃, separating and purifying the obtained reactant to obtain an intermediate product 3 a;
s2, taking the intermediate product 3a, the small molecular alcohol and the metal catalyst in a second solvent, adding alkali, introducing inert gas, stirring and reacting at the temperature of 100-160 ℃ for 5-48 h, cooling to room temperature after the reaction is finished, filtering, distilling to obtain a crude product of the target product, and further purifying to obtain a fine product of the target product.
Preferably, in step S1, the first solvent is one or two selected from methanol, dichloromethane and chloroform.
Preferably, in the step S1, the reaction time is 5-12 h.
Preferably, in step S1, the amount of p-methoxypropiophenone added is 1 to 2 parts by mole, most preferably 1.2 parts by mole, the amount of the first solvent added is 2 liters, and the amount of potassium tert-butoxide added is 0.5 part by mole, based on 1 part by mole of 2-amino-3-pyridinecarbaldehyde.
Preferably, in step S2, the distillation method is distillation under reduced pressure.
Preferably, in step S2, the small molecule alcohol is selected from methanol, ethanol or isopropanol, the metal catalyst is selected from one or a combination of two or more of cupric acetate, cuprous chloride, cupric chloride, ferric chloride, cobalt acetate, palladium acetate, tetrakis (triphenylphosphine) palladium, cobalt chloride, ferrous chloride and manganese acetate; the second solvent is one or the combination of more than two of acetonitrile, 1, 4-dioxane, toluene, p-xylene, methanol, tertiary amyl alcohol and water; the alkali is one or the combination of more than two of sodium carbonate, sodium hydroxide, sodium hydride, sodium methoxide, potassium tert-butoxide, sodium tert-butoxide and triethylamine.
Preferably, in the step S2, the molar ratio of the intermediate product 3a to the small molecular alcohol is 1: 1-20; the molar ratio of the intermediate product 3a to the alkali is 1: 0.5-5.
Preferably, in step S2, the metal catalyst is used in an amount of 0.006 to 0.5 mol parts and the second solvent is used in an amount of 2 to 20 liters, based on 1 mol part of the intermediate product 3 a.
Preferably, in the step S1 and/or S2, the purification method is thin layer chromatography or column chromatography.
More preferably, the eluent used for the column chromatography purification is a mixed solution of dichloromethane and ammonia methanol, wherein the volume ratio of dichloromethane to ammonia methanol is preferably 20-100: 1.
Preferably, in step S2, the reaction vessel is a schlenk tube (schlank tube), and the inert gas is nitrogen or argon.
The invention also comprises the application of the fluorescent compound in the formula (I) in mercury ion detection. And a fluorescent probe, a high-sensitivity sensor and a mercury ion detection instrument containing the fluorescent compound.
The invention has the beneficial effects that:
(1) 2-amino-3-pyridylaldehyde and p-methoxypropiophenone are used as main raw materials to synthesize a target compound 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) in two steps, and the method has the advantages of simple synthesis steps, safe operation of a synthesis method, non-toxic raw materials, low price and good adaptability to functional groups;
(2) the excitation and emission spectra of the fluorescent compound of the invention are in the visible region, for Hg2+High selectivity and sensitivity, good chemical stability, good water solubility, and suitability for Hg in water environment system2+Detection of (3).
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of an intermediate product 2- (4-methoxyphenyl) -3-methyl-1, 8-naphthyridine in the example of the invention;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of an intermediate product 2- (4-methoxyphenyl) -3-methyl-1, 8-naphthyridine in the example of the invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of a target product 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) of an embodiment of the invention;
FIG. 4 is the nuclear magnetic resonance carbon spectrum of the target product 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) in the example of the invention;
FIG. 5 is a graph showing the fluorescence performance test results of the target product 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) under different metal ion conditions in the examples of the present invention;
FIG. 6 shows that the target product of 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) in different Hg according to the example of the present invention2+Fluorescence property test result chart at concentration.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
Example 1
The method comprises the following steps: adding 5mmol of 2-amino-3-pyridylaldehyde and 6mmol of p-methoxypropiophenone into a round-bottom flask, adding 2.5mmol of potassium tert-butoxide and 10ml of ethanol as a solvent, reacting at 60 ℃ for 5h, separating and purifying to obtain an intermediate product 3 a.
Step two: 0.5mmol of intermediate 3a, 0.5mmol of isopropanol, 0.5mmol of sodium hydride, 0.05mmol of cobalt acetate, 1.2ml of 1, 4-dioxane were added to a schlenk tube, and N was charged2Protecting, stirring and reacting for 5h at 160 ℃, stopping heating and stirring, cooling to room temperature, filtering, decompressing and rotary evaporating to remove the solvent, and then separating and purifying by column chromatography, wherein the eluent of the column chromatography is a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1, and the target product 4a is obtained as a yellow solid with the yield of 48%.
The nuclear magnetic resonance hydrogen spectrum and the carbon spectrum of the intermediate product 3a are respectively shown in fig. 1 and fig. 2, and the structural characterization data are as follows:
m.p.:140-141℃;1H NMR(400MHz,CDCl3):9.04(s,1H),8.10(d,J=7.7Hz,1H),7.98(s,1H),7.70(d,J=7.8Hz,2H),7.41(d,J=3.8Hz,1H),7.00(d,J=7.8Hz,2H),3.86(s,3H),2.55(s,3H).
13C NMR(101MHz,CDCl3):δ162.83,160.00,154.84,152.81,137.75,135.87,132.58,130.87,130.56,121.68,121.58,113.44,55.31,20.86.IR(KBr):3022,2952,1549,1602,1486,1010,801cm-1.
MS(EI,m/z):250[M]+.
from the above data, it was concluded that intermediate 3a was 2- (4-methoxyphenyl) -3-methyl-1, 8-naphthyridine.
The nuclear magnetic resonance hydrogen spectrum and the carbon spectrum of the obtained target product 4a are respectively shown in fig. 3 and 4, and the structural characterization data are as follows:
m.p.:268-269℃;1H NMR(400MHz,CDCl3):δ9.87(s,1H),9.07(s,1H),8.24(d,J=8.3Hz,1H),8.07(d,J=4.5Hz,2H),8.01(s,1H),7.73(d,J=8.2Hz,2H),7.68(d,J=8.3Hz,2H),7.02(t,J=8.9Hz,4H),3.88(s,3H),3.87(s,3H),2.56(s,3H),2.54(s,3H).
13C NMR(101MHz,CDCl3):δ164.04,163.48,160.16,160.07,156.47,155.13,154.77,151.94,138.51,137.49,137.27,135.23,132.53,132.42,131.92,131.18,131.01,130.98,130.71,121.13,120.96,119.09,113.59,113.48,55.33,21.00,20.83.
IR(KBr):3043,2958,2928,2837,1601,1514,1492,1415,1299,1250,1176,836,809,737cm-1.
HRMS(ESI):Calcd.for C32H26N4O2[M+H]+:499.2129;found:499.2129.
the target product 4a is presumed to be 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) according to the data, and the structure is shown as the following formula.
Figure BDA0001812332320000041
Example 2
The method comprises the following steps: the same as in example 1, except that the reaction temperature was 25 ℃.
Step two: 0.5mmol of the intermediate 3a, 2.0mmol of ethanol, 0.25mmol of sodium hydride, 0.25mmol of cuprous chloride and 1.2ml of 1, 4-dioxane were added to a schlenk tube, and N was charged2Protecting, stirring at 100 deg.C for 48 hr, stopping heating and stirring, cooling to room temperatureFiltering, decompressing and rotary distilling to remove the solvent, and then separating and purifying by column chromatography, wherein the eluent of the column chromatography is a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1, and the target product 4a of yellow solid is obtained with the yield of 49 percent.
The characterization results of the obtained intermediate product 3a and the target product 4a are the same as in example 1.
Example 3
The method comprises the following steps: the same as in example 1, except that the reaction time was 6 hours.
Step two: to a schlenk tube were added 0.5mmol of intermediate 3a, 2.0mmol of isopropanol, 0.5mmol of sodium hydride, 0.005mmol of tetrakis (triphenylphosphine) palladium, 1.2ml of 1, 4-dioxane, and N was charged2Protecting, stirring and reacting for 16h at 130 ℃, stopping heating and stirring, cooling to room temperature, filtering, performing reduced pressure rotary evaporation to remove the solvent, and performing column chromatography separation and purification by using a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1 as eluent of the column chromatography to obtain a yellow solid target product 4a with the yield of 36%.
The characterization results of the obtained intermediate product 3a and the target product 4a are the same as in example 1.
Example 4
The method comprises the following steps: the same as in example 3, except that the reaction temperature was 80 ℃.
Step two: 0.5mmol of intermediate 3a, 2.0mmol of isopropanol, 0.5mmol of sodium hydroxide, 0.003mmol of ferric chloride, 1.2ml of 1, 4-dioxane were added to a schlenk tube and charged with N2Protecting, stirring and reacting for 16h at 130 ℃, stopping heating and stirring, cooling to room temperature, filtering, performing reduced pressure rotary evaporation to remove the solvent, and performing column chromatography separation and purification by using a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1 as eluent of the column chromatography to obtain a yellow solid target product 4a with the yield of 53%.
The characterization results of the obtained intermediate product 3a and the target product 4a are the same as in example 1.
Example 5
The method comprises the following steps: the same as example 3, except that the solvent was dichloromethane.
Step two: in schlenk tube addAdding 0.5mmol of intermediate product 3a, 2.0mmol of methanol, 2.5mmol of sodium hydride, 0.005mmol of manganese acetate and 1.2ml of toluene, and charging N2Protecting, stirring and reacting for 16h at 130 ℃, stopping heating and stirring, cooling to room temperature, filtering, performing reduced pressure rotary evaporation to remove the solvent, and performing column chromatography separation and purification by using a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1 as eluent of the column chromatography to obtain a yellow solid target product 4a with the yield of 54%.
The characterization results of the obtained intermediate product 3a and the target product 4a are the same as in example 1.
Example 6
The method comprises the following steps: the same as in example 3.
Step two: 0.5mmol of intermediate 3a, 10.0mmol of isopropanol, 0.5mmol of sodium hydride, 0.25mmol of ferrous chloride and 1.2ml of p-xylene are added into a schlenk tube, and N is charged2Protecting, stirring and reacting for 16h at 130 ℃, stopping heating and stirring, cooling to room temperature, filtering, performing reduced pressure rotary evaporation to remove the solvent, and performing column chromatography separation and purification by using a mixed solvent of dichloromethane and ammonia methanol with the volume ratio of 100:1 as eluent of the column chromatography to obtain a yellow solid target product 4a with the yield of 44%.
The characterization results of the obtained intermediate product 3a and the target product 4a are the same as in example 1.
Test example
Test examples the target product 4a obtained in examples 1 to 6 was subjected to fluorescence property test. The method comprises the following steps:
(1) probe solution preparation
Preparing a methanol solution of 7,7' -bis (4-methoxyphenyl) -6,6' -dimethyl-2, 3' -bi (1, 8-naphthyridine) with the concentration of 100 mu M, namely a probe solution, and storing at normal temperature.
(2) Preparation of metal ion solution
The metal ions include: mg (magnesium)2+,Fe2+,Cu+,Cu2+,Sn4+,Co2+,Mn2+,K+,Li+,Ba2+,Ca2+,Cd2+,Ni2 +,Fe3+,Al3+And Hg2+Solutions thereof are respectively prepared fromThe hydrochloride was prepared as follows: for each metal ion, a certain amount of hydrochloride is weighed respectively and then dissolved in distilled water to prepare 10-2And storing the metal ion solution in mol/L for later use.
(3) Fluorescence property test
Test example 1
Liquid to be detected: taking 0.5ml of the probe solution prepared in the step (1), 0.5ml of any one metal ion solution prepared in the step (2) and 4ml of CH3OH-H2And mixing the O (v: v ═ 1:1) solutions to obtain a solution to be tested of the metal ions. Preparing the solution to be tested of each metal ion in the step (2) by the same method.
Blank liquid: 0.5mL of the probe solution prepared in step (1) was mixed with 2.5mL of water and 2mL of a methanol solution.
After the fluorescence spectrum analysis, in the liquid to be detected, when the metal ion is Mg2+,Fe2+,Cu+,Cu2+,Sn4+,Co2+,Mn2+,K+,Li+,Ba2+,Ca2+,Cd2+,Ni2+,Fe3+,Al3+When the fluorescence intensity changes little, only Hg2+The fluorescence intensity of the test solution showed a significant fluorescence decay (see FIG. 5 for details, all the metal ions are labeled "4 a + M" in common).
Test example 2
Furthermore, in order to verify the specificity of the fluorescent compound to mercury ions, a competition experiment is also carried out. Hg is introduced2+Adding the solution (10 mu M) and the solution of any other metal ion with the same concentration into the probe solution prepared in the step (1), and respectively testing other competitive ions for the fluorescent compound Hg2+The results of the detection are shown in FIG. 5 (the corresponding test solutions are collectively denoted as "4 a + M + Hg"). It can be seen that the target product 4a is coupled to Hg before and after the addition of other competing ions2+Was almost unchanged, indicating that the fluorescent compound probe was designed for Hg2+Has strong selectivity and can meet the requirements of practical application.
Test example 3
In the target product4a methanol aqueous solution to which Hg of various concentrations was added2+Testing the fluorescence to determine the Hg of the compound2+Detection range and detection limit. The results are shown in FIG. 6, and it can be seen that the fluorescence intensity of Compound 4a varies with Hg2+The increase in concentration gradually decreased as Hg2+At concentrations up to 20. mu.M, the fluorescence intensity of the compound decayed dramatically. The compound is to Hg2+The detection range is from 0.5 mu M to 20 mu M, and the detection limit is 5 multiplied by 10-7μ M, indicating that the compound is para to Hg2+The method has good detection capability and high practical application value, and can be used for high-sensitivity sensors, mercury ion detection instruments and the like. The compound has good water solubility, so the compound can be suitable for Hg in a water environment system2+Detection of (3).
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.

Claims (10)

1. A fluorescent compound having the structure shown in formula (I):
Figure FDA0001812332310000011
2. a method of synthesizing a fluorescent compound according to claim 1, comprising the steps of:
s1, taking 2-amino-3-pyridylaldehyde and p-methoxypropiophenone, adding potassium tert-butoxide, dissolving with a first solvent, reacting at 25-80 ℃, and separating and purifying the obtained reactant to obtain an intermediate product;
s2, taking the intermediate product, the small molecular alcohol and the metal catalyst into a second solvent, adding alkali, introducing inert gas, stirring and reacting for 5-48 h at the temperature of 100-160 ℃, then cooling to room temperature, filtering, distilling to obtain a crude product of the target product.
3. The method for synthesizing a fluorescent compound according to claim 2, wherein in step S1, the first solvent is one or two selected from methanol, dichloromethane and chloroform.
4. The method for synthesizing a fluorescent compound according to claim 2, wherein the reaction time in step S1 is 5 to 6 hours.
5. The method for synthesizing a fluorescent compound according to any one of claims 2 to 4, wherein in step S1, the amount of p-methoxypropiophenone added is 1 to 2 parts by mole, the amount of the first solvent added is 2 liters, and the amount of potassium tert-butoxide added is 0.5 part by mole, based on 1 part by mole of 2-amino-3-pyridinecarbaldehyde.
6. The method for synthesizing a fluorescent compound according to claim 2, wherein in step S2, the small molecule alcohol is selected from methanol, ethanol, or isopropanol, the metal catalyst is selected from one or a combination of two or more of copper acetate, cuprous chloride, copper chloride, ferric chloride, cobalt acetate, palladium acetate, tetrakis (triphenylphosphine) palladium, cobalt chloride, ferrous chloride, and manganese acetate; the second solvent is one or the combination of more than two of acetonitrile, 1, 4-dioxane, toluene, p-xylene, methanol, tertiary amyl alcohol and water; the alkali is one or the combination of more than two of sodium carbonate, sodium hydroxide, sodium hydride, sodium methoxide, potassium tert-butoxide, sodium tert-butoxide and triethylamine.
7. The method for synthesizing a fluorescent compound according to claim 2 or 6, wherein in the step S2, the molar ratio of the intermediate product to the small molecular alcohol is 1: 1-20; the molar ratio of the intermediate product to the alkali is 1: 0.5-5; the amount of the metal catalyst is 0.006-0.5 mol parts and the amount of the second solvent is 2-20L relative to 1 mol part of the intermediate product.
8. The method for synthesizing a fluorescent compound according to claim 2, wherein in step S1, the purification method is thin layer chromatography or column chromatography.
9. The method for synthesizing a fluorescent compound according to claim 8, wherein the eluent obtained by column chromatography purification is a mixed solution of dichloromethane and ammonia methanol, and the volume ratio of dichloromethane to ammonia methanol is 20-100: 1.
10. Use of the fluorescent compound of claim 1 in mercury ion detection.
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