CN109810103B - Compound with aggregation-induced emission effect, preparation method and application - Google Patents
Compound with aggregation-induced emission effect, preparation method and application Download PDFInfo
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- CN109810103B CN109810103B CN201910087170.0A CN201910087170A CN109810103B CN 109810103 B CN109810103 B CN 109810103B CN 201910087170 A CN201910087170 A CN 201910087170A CN 109810103 B CN109810103 B CN 109810103B
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Abstract
The invention discloses a compound with aggregation-induced emission effect, a preparation method and application thereof, wherein the structural formula of the compound is
The compound not only has aggregation-induced emission effect, but also has effect on CN‑The detection has the effects of wider linear range, high sensitivity, good selectivity and the like.
Description
Technical Field
The invention relates to the technical field of fluorescence detection, in particular to a compound with aggregation-induced emission effect, and a preparation method and application thereof.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
With the development of science, the safety of living environment and food has attracted a great deal of attention. Cyano anions have received great attention because of their great harm and toxicity to the human body. The cyano anion interacts primarily with metal ions in cytochrome P450, resulting in its loss of ability to transport electrons in the respiratory chain, with subsequent damage to the central nervous system and even death. Even so, cyanide is widely used in many modern industries, such as metallurgy, electroplating, synthetic fibers, herbicides, etc., causing significant pollution of water and the natural environment, and allowing cyano anions to enter the human body through water and food chains. However, the World Health Organization (WHO) stipulates that the maximum safe concentration allowed in drinking water is 1.9 μ M. Therefore, it is necessary to develop colorimetric and fluorescent chemical sensors for detecting cyanide ions in an environment at low cost, with simplicity, high sensitivity and high selectivity. CN based on multiple mechanisms has been developed-Colorimetric and fluorometric chemical sensors for detection, e.g. Intramolecular Charge Transfer (ICT)[26,27]Excited intramolecular proton transfer (ESIPT), and light-induced electron transfer (PET). However, most are used for CN-The sensing material for detection is easily soluble in organic solvent but insoluble in water, and most of CN-Present in water such as industrial waste water, drinking water and laboratory discharge water, etc. Thus, the development of CN detection in aqueous solution-Is of importance.
Sensing materials with aggregation-inducing effect (AIE) as a means for detecting CN in aqueous solutions-Is a good choice. The AIE-active molecules do not fluoresce in solvents, but fluoresce strongly due to the formation of aggregates in aqueous solutions. However, to the best of the inventors' knowledge, both the AIE effect and the effect on CN-Few sensing materials have good sensing properties. Therefore, it is desirable to provide a method for detecting CN with AIE effect-The sensing material of (1).
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a compound with aggregation-induced emission effect, a preparation method and application thereof, wherein the compound not only has the aggregation-induced emission effect, but also has the effect on CN-The detection has the effects of wider linear range, high sensitivity, good selectivity and the like.
In order to achieve the purpose, the technical scheme of the invention is as follows:
in a first aspect, a compound having an aggregation-induced emission effect has the following structural formula:
in a second aspect, a process for the preparation of the above compound comprises starting from intermediate 1 by the following reaction scheme:
the invention provides a synthesis method of the compound, and the yield of the compound is high and can reach 90%.
In a third aspect, there is provided a detection sensor comprising the above compound as a detection sensor material. Experiments show that the compound prepared by the invention has aggregation induction effect, and the compound prepared by the invention can be used as a detection sensing material.
In a fourth aspect, use of a compound or a detection sensor as described above for detecting a cyano anion. Further experiments show that the compound prepared by the invention is used as a sensing material for detecting CN-Has high sensitivity and good selectivity, so the compound prepared by the invention is used for detecting CN-Has better effect.
In a fifth aspect, a method for detecting cyano anion is to add a sample to be detected into a solution containing the above compound, and perform detection by using ultraviolet-visible light spectrum or fluorescence spectrum.
The invention has the beneficial effects that:
the invention provides a compound with a novel structure, which is an ICT-based D-pi-A type sensing material, wherein dibenzothiophene is used as an electron donating group, and barbituric acid is used as an electron withdrawing group. Naked eye colorimetric and fluorescence sensing material DTB shows CN in 99% DMSO aqueous solution-High sensitivity and good selectivity of detection. Sensing material DTB to CN-The kit has the advantages of quick response, high anti-interference capability, wide linear range and lower detection limit (21.6 nM).
Drawings
The accompanying drawings, which are included to provide a further understanding of the disclosure, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure and are not to limit the disclosure.
FIG. 1 shows DTB in DMSO/H2In O mixed solution with fwA varying ultraviolet spectrogram;
FIG. 2 shows DTB in DMSO/H2In O mixed solution with fwA varied fluorescence spectrum;
FIG. 3 shows DTB and fwThe curve of the corresponding wavelength and fluorescence intensity, wherein the dots are the wavelength and the five-pointed star is the fluorescence intensity;
FIG. 4 is a graph of the selective UV spectra of DTB in 99% DMSO in water for various anions (2.0 equiv);
FIG. 5 is a graph of the selective fluorescence spectra of DTB in 99% DMSO in water for various anions (2.0 equiv);
FIG. 6 shows the DTB detection CN-Histogram of anti-interference experiments;
FIG. 7 shows DTB in 99% DMSO in water at various concentrations of CN-(0-2.0 equivalent) ultraviolet spectrum at the time of dropping;
FIG. 8 shows DTB in 99% DMSO in water for different concentrations of CN-Detected fluorescence spectrum with the inset being the fluorescence intensity of DTB at 585nm as a function of CN-A point plot of concentration change;
FIG. 9 shows DTB vs CN-The detection limit line graph of (2).
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
The disclosure provides a compound with aggregation-induced emission effect, and a preparation method and application thereof. The compound not only has aggregation-induced emission effect, but also has effect on CN-The detection has the effects of wider linear range, high sensitivity, good selectivity and the like.
In one exemplary embodiment of the present disclosure, a compound having aggregation-induced emission effect is provided, having the following structural formula:
in another embodiment of the present disclosure, a method for preparing the above compound is provided, which comprises using intermediate 1 as a starting material, and preparing the following reaction scheme:
the invention provides a synthesis method of the compound, and the yield of the compound is high and can reach 90%.
In one or more embodiments of this embodiment, the process comprises: the intermediate 1 and barbituric acid are subjected to aldol condensation reaction to obtain the compound.
In this series of examples, the conditions of the aldol condensation reaction were: heating and refluxing the mixture in a solvent. Because the barbituric acid itself is acidic, the addition of an acidic catalyst may not be required.
In the series of examples, the molar ratio of the intermediate 1 to the barbituric acid is 1: 0.9-1.1.
Since intermediate 1 is not industrialized, the present disclosure provides a preparation from an already industrialized compound as a raw material, and the synthetic route is as follows:
wherein, the synthesis process of the intermediate 1 can refer to: wei Zhi Jian, Zhang Xian, Yaojin Water, the synthesis of a novel two-photon compound 3- (1-vinyl furan) dibenzothiophene and the optical properties thereof, synthetic chemistry, No. 18, No. 3, page 348 and 351 in 2010.
In a third embodiment of the present disclosure, there is provided a detection sensor, wherein the compound is used as a detection sensing material. Experiments show that the compound prepared by the method has an aggregation-induced emission effect, and the compound prepared by the method can be used as a detection sensing material.
In one or more embodiments of this embodiment, including an aqueous dimethyl sulfoxide (DMSO), the compound is dissolved in the aqueous dimethyl sulfoxide (DMSO). Experiments show that the aggregation induction effect of the compound in a DMSO (dimethylsulfoxide) aqueous solution is better. Among them, when the percentage of water in the DMSO aqueous solution was 99%, the aggregation-inducing effect of the compound in the solution was the best, and the fluorescence intensity was increased by 12.9 times as compared with that in the pure DMSO solvent.
In a fourth embodiment of the present disclosure, there is provided a use of the above compound or the detection sensor for detecting a cyano anion. Further experiments show that the compound prepared by the method can be used as a sensing material for detecting CN-Has high sensitivity and good selectivity, so the compound prepared by the method is used for detecting CN-Has better effect.
In a fifth embodiment of the present disclosure, a method for detecting cyano anion is provided, wherein a sample to be detected is added to a solution containing the above compound, and detection is performed by using ultraviolet-visible light spectrum or fluorescence spectrum.
In one or more embodiments of this embodiment, the detection wavelength is 580-590 nm when fluorescence spectroscopy is used. When the detection wavelength is in this range, CCN -The Fluorescence (FL) intensity decreased significantly when increasing from 0 to 30. mu.M. The detection limit is 21.6nM, and the linear concentration range is 0-30 μ M.
In order to make the technical solutions of the present disclosure more clearly understood by those skilled in the art, the technical solutions of the present disclosure will be described in detail below with reference to specific embodiments.
Examples
Preparation of the Compounds
The preparation route of the compound is as follows:
wherein, the synthesis process of the intermediate 1 refers to Wenzhi Jian, Zhangzhou, Yaojin water, the synthesis of a novel two-photon compound 3- (1-vinyl furan) dibenzothiophene and the optical performance thereof, synthetic chemistry, No. 18, No. 3, page 348 and 351 in 2010.
Using dibenzothiophene as raw material and TiCl4The promoted Friedel-crafts reaction is carried out to obtain 3-formyl dibenzothiophene (1); intermediate 1(0.3g, 1.42mmol) and barbituric acid (0.18g, 1.42mmol) were mixed in redistilled absolute ethanol (10mL) and stirred under reflux for 5 hours, then the mixture was cooled and filtered with suction to obtain the final compound (hereinafter abbreviated as DTB), which was washed with ethanol and dried under vacuum to obtain a pale yellow solid (0.41g, yield 90%).1H NMR:(400MHz,DMSO–d6)δ＝11.44(s,1H),11.31(s,1H),9.18(s,1H),8.51(s,1H),8.37-8.42(m,2H),8.16(d,J＝8.0Hz,1H),8.09-8.12(m,1H),7.57-7.59(m,2H)；FT–IR:(KBr,cm–1)ν＝3252(N–H),3014(C–H),1722(C＝O),1663(C＝C)；HRMS(ESI):m/z[M+H]+Calculated value C17H11N2O3323.0490, found 323.0484.
The prepared DTB is subjected to Aggregation Induction Effect (AIE) performance study and cyanide anion (CN)-) The detection results are respectively as follows:
AIE Effect of DTB
The AIE effect of DTB was studied by uv spectroscopy and fluorescence spectroscopy. As shown in FIG. 1, the absorption peak between 290nm and 330nm is assigned to the π - π of barbituric acid and dibenzothiophene*And (4) electron transition. In addition, the DTB molecule shows a distinct absorption peak at 395nm, which is attributable to the Intramolecular Charge Transfer (ICT) from dibenzothiophene to barbituric acid.
Compound DTB in pure DMSO solvent and in DMSO/H2Fluorescence spectra in O-mixtures as shown in fig. 2, since water is a poor solvent, increasing the water content in DMSO solvent can promote aggregation of DTB, thereby enhancing fluorescence intensity. Therefore, by increasing the percentage of water in the mixed solution of DMSO and water (volume ratio of water to DMSO, recorded as f)w) To prepare nanoaggregates of DTB. FIG. 3 is a drawingIs plotted at different fwThe trend of the fluorescence intensity and wavelength of the DTB.
As shown in FIG. 2, DTB was dissolved in pure DMSO solvent (C)DTB30 μ M), while the DTB powder fluoresces strongly, indicating that DTB has a strong AIE effect. Furthermore, the fluorescence intensity (f) of DTB in pure DMSO solventw0%) was very weak. When f iswBelow 80%, the fluorescence intensity of DTB decreases with increasing water content. However, when fwThe increase to 90% begins to increase the fluorescence intensity. Further, the fluorescence intensity is fwA maximum is reached at 99% vs fluorescence intensity (f) in pure DMSO solventw0%) compared to 12.9 times. These data demonstrate that compound DTB has an AIE effect.
As can be seen from FIG. 3, when fwWhen the concentration is increased from 0% to 99%, the emission peak of DTB is red-shifted from 501.4nm to 581.8 nm. When DTB molecules aggregate at high water contents, the red shift of the emission peak can be attributed to the formation of pi-pi bonds. When f iswAt not more than 80%, the polarity of the mixed solvent increases due to the increase in the water content, and the intramolecular charge transfer increases, so that with fwThe fluorescence becomes weaker. When f iswUp to 90%, the DTB molecules begin to aggregate, producing nanoparticles. Due to the aggregation-induced effect of DTB, its fluorescence is significantly enhanced.
Selectivity and interference resistance of DTB to anions
A series of anions (F)-，Cl-，Br-，I-，NO3 -，AcO-，HCO3 -，CO3 2-，SO4 2-，HSO4 -And CN-Etc.) were added to the solutions containing DTB (1mM), respectively, and the uv spectrum and the fluorescence spectrum thereof were tested. FIGS. 4 and 5 show that even with the addition of 10 equivalents of other common anions (except CN)-Outer), ultraviolet spectrum and fluorescence spectrum (λ) of DTBex＝400nm，λem582nm) also had no significant change. In the presence of CN-In the case of (2), the maximum absorption peak of DTB at 395nm was lowered, while a new absorption peak appeared at 285nm, and the fluorescence of DTB at 582nmThe intensity of the light emission peak is significantly reduced. This spectral change indicates a change in the chemical structure of DTB due to CN-The nucleophilic addition reaction with DTB has blocked intramolecular charge transfer, thereby affecting its spectral properties.
To further illustrate DTB as a detection CN-The feasibility of a highly selective fluorescence sensor. As shown in fig. 6, anti-interference experiments were performed on sensor DTB by adding 2.0 equivalents of each anion to a 99% DMSO aqueous solution. The results show that the common anion pair DTB detects CN-Has little influence, and DTB can be used as CN-The fluorescence sensor has excellent selectivity and good anti-interference performance.
DTB to CN-Investigation of the detection
DTB is added into 99% DMSO aqueous solution with CN of different concentrations-The UV spectrum of (2) changes as shown in FIG. 7 with CN-Increases from 0 to 2.0 equivalents, and the absorption peaks of DTB at 280nm, 315nm and 395nm gradually decrease. This course of change indicates DTB and CN-Nucleophilic addition reaction occurs between the two, and the conjugated system of DTB is CN-Destroyed and indicates DTB and CN-The reaction between them produces a new complex.
DTB in 99% DMSO aqueous solution versus CN at various concentrations was further investigated by fluorescence spectroscopy-The detection performance of (2). As shown in fig. 8, with CN-The concentration (0-2.0 equivalent) increased, and the fluorescence emission peak at 582nm gradually decreased due to the blocking of Intramolecular Charge Transfer (ICT) of DTB. The inset in FIG. 8 is the fluorescence intensity of DTB at 582nm as CN-(0-2.0 equivalents) as a function of concentration. It can be seen that when C isCN -The fluorescence intensity decreased significantly when the concentration increased from 0 to 30. mu.M. When C is presentCN -Above 30. mu.M, the fluorescence intensity remained almost unchanged, indicating CN-Saturated in the solution, the number of addition reactions with DTB was 1: 1. As shown in fig. 9, sensor DTB is coupled to CN-The Detection Limit (DL) of (2) is 21.6nM, the linear concentration range is 0-30 mu M, which is far lower than CN in drinking water-The allowable content of (a).
The above description is only a preferred embodiment of the present disclosure and is not intended to limit the present disclosure, and various modifications and changes may be made to the present disclosure by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present disclosure should be included in the protection scope of the present disclosure.
Claims (9)
1. A compound having an aggregation-induced emission effect, characterized by the structural formula:
2. a process for the preparation of the compound of claim 1, characterized in that it is obtained by aldol condensation of intermediate 1 with barbituric acid, the reaction scheme being as follows:
3. the process according to claim 2, wherein the aldol condensation reaction is carried out under the following conditions: heating and refluxing the mixture in a solvent.
4. The process according to claim 2, wherein the molar ratio of intermediate 1 to barbituric acid is 1: 0.9-1.1.
5. A detection sensor characterized in that the compound according to claim 1 is used as a detection sensor material.
6. The test sensor of claim 5, comprising an aqueous solution of dimethyl sulfoxide in which the compound is dissolved.
7. Use of the compound of claim 1 or the detection sensor of claim 5 for detecting a cyano anion; the applications are non-disease diagnostics and therapeutics.
8. A method for detecting a cyano anion, characterized in that a sample to be detected is added to a solution containing the compound of claim 1, and detection is performed by ultraviolet-visible light spectroscopy or fluorescence spectroscopy; the method is applied to diagnosis and treatment of non-diseases.
9. The method of claim 8, wherein the detection wavelength is 580 to 590nm when fluorescence spectroscopy is used for detection.
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