CN114105816A - Fe in dynamic monitoring water3+Fluorescent dye and application thereof - Google Patents

Fe in dynamic monitoring water3+Fluorescent dye and application thereof Download PDF

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CN114105816A
CN114105816A CN202111459325.2A CN202111459325A CN114105816A CN 114105816 A CN114105816 A CN 114105816A CN 202111459325 A CN202111459325 A CN 202111459325A CN 114105816 A CN114105816 A CN 114105816A
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fluorene
fluorescent dye
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metal ions
fluorescent
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徐静
陈玉婷
王志刚
胡慧
杜鹏
徐冬梅
张晓蕾
赵淑曼
赵宏睿
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Dezhou University
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Abstract

The invention provides a method for dynamically monitoring Fe in water3+The fluorescent dye and the application thereof relate to the technical field of organic dye detection function; the fluorene fluorescent dye provided by the invention is prepared by taking benzaldehyde and 2-aminofluorene as reaction raw materials through one-step polymerization reaction with high yield. As the imine group in the fluorene dye molecule is not only the conjugated bridging group of fluorene and phenyl but also the complexing site of metal ions, and is combined with Fe3+Resulting in a sensitive "off-on-off" dual-conversion fluorescence detection signal after complexation, for Fe3+Has the functions of quantitative and qualitative detection; the preparation method has the advantages of mild reaction conditions, simple preparation process, low price of raw materials, easy implementation and the like, is suitable for industrial popularization, and creates favorable conditions for the popularization and application of the fluorene fluorescent dye molecule.

Description

Fe in dynamic monitoring water3+Fluorescent dye and application thereof
Technical Field
The invention relates to the technical field of organic dye detection functions, in particular to a pair of Fe3+Fluorene fluorescent dye molecules with sensitive 'off-on-off' fluorescence detection signals and application thereof.
Background
Metal ions have wide application in industrial production, but when they are discharged in a cationic form along with industrial wastewater into the nature, they can seriously pollute the whole water system and cause great harm to the ecosystem and human living environment. In particular, metal ions discharged into the ecological environment are difficult to degrade, and are easy to concentrate and expand in the biological chain; once people eat water and food polluted by metal ions, the metal ions can be continuously accumulated in human bodies, and the human health is seriously threatened, so that the detection of the metal ions plays a significant role. Iron, for example, is the most abundant transition metal in the human body and contributes to various biological functions. However, excessive iron ions in the body may cause liver dysfunction, myocardial damage, and the like. In addition, iron content is also associated with certain neurological disorders, such as Parkinson's disease and Alzheimer's disease. Therefore, the development of fast, easy-to-operate and real-time iron ion detection method has become a hot spot of competitive research in the fields of chemistry, biological environment, medicine and the like.
Among many methods for analyzing and detecting iron ions, the fluorescence monitoring technology has received more and more attention due to its advantages of simplicity, rapidness, real-time monitoring, high sensitivity, and being capable of breaking through the detection limit of the conventional analytical instrument. The method can realize the detection of the iron ions on the molecular level by utilizing the spectral information generated by the selective combination of the fluorescent molecular probe on the iron ions, and has the advantages of simplicity, convenience, sensitivity, accuracy, rapidness and low cost. At present, there are many related to Fe3+The reported fluorescent probe of (4), but reported Fe3+Fluorescent molecular probes mostly vary with their concentration, fluorescenceThe intensity signal is only increased or decreased singly, while the fluorescence signal is dependent on Fe3+Few reports have been reported for sensitive molecular probes that exhibit a "off-on-off" bi-directional change in concentration. While to Fe in human practical work3+The need for dynamic change in concentration detection is increasing. Therefore, the development of sensitive, easy-to-prepare and dynamic Fe detection3+The fluorescent molecular probe is urgently needed in various monitoring fields at present.
In the construction process of the fluorescent molecular probe, the rigidly conjugated fluorene group has the characteristics of higher light stability, easy modification of structure and the like, and is an excellent fluorescent signal group. The imine group easy to synthesize has stronger metal coordination capacity, and the complexation selectivity of the imine group to metal ions can be increased by introducing the imine group into fluorescent molecules; and the p-pi conjugation effect after the imine group is connected with the fluorophore can increase the conjugation of the fluorescent molecule, and when the nitrogen atom in the imine group is coordinated with the metal ion, the change of the conjugation degree of the fluorescent molecule can be caused, so that the fluorescent molecule shows sensitive spectral signal change. After combining the two, a series of fluorescent molecular probes [ Q.xu, X.Wang, G.Xing, Y.Zhang ] with different identification performances are prepared,RSC Adv, 2013, 3, 15834-15841; F. Wang, C. Li, X. Zhang,A. Wang,L. Zhou,C. Jia,J. Xu, Y. Chen,Dyes and Pigments, 2019, 171, 107667]. But for Fe3+Iminofluorene fluorochromes with sensitive "off-on-off" fluorescence detection signals have not been reported.
Disclosure of Invention
The invention aims to provide a method for treating Fe in water3+Fluorene fluorochrome molecules with sensitive "off-on-off" fluorescence detection signals.
Another technical purpose of the invention is to provide a method for dynamically detecting Fe in water for people to work and live3+The method has the advantages of rapidness, sensitivity, easy operation, low cost, qualitative/quantitative detection and the like.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
can dynamic detection aquatic Fe3+The molecular structure of the fluorene fluorescent dye is as follows:
Figure 100002_DEST_PATH_IMAGE002
can dynamic detection aquatic Fe3+The preparation method of the fluorene fluorescent dye comprises the following steps:
placing alpha mmol benzaldehyde into a round-bottom flask containing beta mL absolute ethyl alcohol, and heating to reflux; then adding gamma mmol 2-aminofluorene and continuing to react for 3-5 hours; filtering the mixture obtained by the reaction, washing with absolute ethyl alcohol, and drying to obtain a tawny fluorene fluorescent dye; the ratio of alpha, beta and gamma is 1:15: 1.
Can dynamic detection aquatic Fe3+The preparation reaction formula of the fluorene fluorescent dye is as follows:
Figure DEST_PATH_IMAGE003
the invention has the following technical effects: the fluorene fluorescent dye contains imine bridging group sensitive to metal ions, and the imine bridging group and Fe3+Resulting in a sensitive spectral signal after complexation; with Fe in aqueous solution3+The concentration is increased continuously, the maximum fluorescence emission of the dye molecule at 370 nm is obviously enhanced and then reduced, and a flexible off-on-off dual-conversion fluorescence detection signal is presented for Fe3+The kit has sensitive quantitative detection performance; the preparation process of the fluorene fluorescent dye provided by the invention has the advantages of low cost of raw materials, simple preparation process, mild reaction conditions, high yield and the like, is suitable for industrial implementation, and creates favorable conditions for popularization and application of the fluorene fluorescent dye.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the compound obtained in example 1-2.
FIG. 2 shows fluorescence emission spectra of fluorene fluorescent dye added with different metal ions in 5% methanol aqueous solution.
FIG. 3 shows the UV absorption spectra of fluorenylene fluorescent dye added with different metal ions in 5% methanol aqueous solution.
FIG. 4 shows that the fluorene fluorescent dye is added with Fe with different concentrations in 5% methanol aqueous solution3+Fluorescence emission spectrum of (1).
Detailed Description
The invention discloses a method capable of dynamically detecting Fe in water3+The molecular structure of the fluorene fluorescent dye is as follows:
Figure DEST_PATH_IMAGE002A
；
the catalyst can be prepared by adopting benzaldehyde and 2-aminofluorene as reaction raw materials through one-step polymerization reaction, and the preparation reaction formula is as follows:
Figure DEST_PATH_IMAGE003A
。
example 1
1 mmol of benzaldehyde is put into a round-bottom flask filled with 15 mL of absolute ethyl alcohol, and then the temperature is raised to reflux; then 1 mmol of 2-aminofluorene is added and the reaction is continued for 3 hours; the mixture obtained by the reaction was filtered, washed with absolute ethanol, and dried to obtain a yellow-brown fluorene fluorescent dye a, 216 mg, with a yield of 80%.
Example 2
1 mmol of benzaldehyde is put into a round-bottom flask filled with 15 mL of absolute ethyl alcohol, and then the temperature is raised to reflux; then adding 1 mmol of 2-aminofluorene and continuing to react for 5 hours; the mixture obtained by the reaction was filtered, washed with absolute ethanol, and dried to obtain a tan fluorene fluorescent dye B, 417 mg, with a yield of 80.3%.
The analysis of the compounds A and B obtained in examples 1-2, respectively, showed that the nuclear magnetic hydrogen spectra were consistent, and the data were as follows: in that1H NMR (CDCl 3400 MHz), delta 8.51 (s, 1H), 7.81 (t, 2H, J = 15.2 Hz), 7.56 (t, 2H, J = 7.2 Hz), 7.48 (s, 1H), 7.42 (d, 2H, J = 4 Hz), 7.36(d, 2H, J = 3.6 Hz), 7.32(d, 1H, J = 16 Hz), 7.28 (m, 2H, J = 8 Hz), 6.99 (d, 1H, J = 7.2 Hz), 3.94 (s, 2H), which is substantially consistent with the theoretical value of the fluorenylfluorescing dye molecule. From this, it was confirmed that compound A, B has the following molecular structure:
Figure DEST_PATH_IMAGE002AA
i.e. a fluorene fluorochrome molecule.
Example 3
The fluorescent detection performance of the fluorene fluorescent dye on different metal ions in 5% methanol water solution is as follows: in 5% aqueous methanol at a concentration of 2X 10-5The mol/L fluorene fluorescent dye has a weak fluorescence emission peak near the 370 nm position; adding 10 times of Fe3+Thereafter, its maximum fluorescence emission at the 370 nm position was quenched; other metal ions, e.g. Li+、Na+、K+、Ba2+、Ca2+、Mg2 +、Co2+、Hg2+、Mn2+、Ni2+、Cd2+、Zn2+After the addition of the plasma metal ions, the maximum fluorescence emission of the compound at the 370 nm position changes little. These show that the fluorene fluorescent dye is p-Fe3+The ions have a unique fluorescence detection response.
Example 4
The ultraviolet absorption detection performance of the fluorene fluorescent dye on different metal ions in 5% methanol water solution is as follows: in 5% aqueous methanol at a concentration of 2X 10-5Two absorption shoulders are formed at the positions of 340 nm and 274 nm of the mol/L fluorene fluorescent dye; adding 10 times of Fe3+Then, the absorption peak at the position of 340 nm is red-shifted to 366 nm, and the absorption peak at the position of 274 nm is blue-shifted to 251 nm; other metal ions, e.g. Li+、Na+、K+、Ba2+、Ca2+、Mg2+、Co2+、Hg2+、Mn2+、Ni2+、Cd2+、Zn2+After the metal ions are added, the ultraviolet absorption spectrum of the compound is hardly changed. These show that the fluorene fluorescent dye is p-Fe3+The ions have double detection responses of ultraviolet absorption and fluorescence.
Example 5
Fluorene fluorescent dye in 5% methanol water solution for different concentrations of Fe3+Fluorescence detection performance of (2): at a concentration of 2X 10-5Fe with different concentrations is respectively added into mol/L fluorene fluorescent dye 5% methanol water solution3+The molar equivalent ratio of the two is 1:0, 1:0.2, 1:0.4, 1:0.6, 1:0.8 and 1:1 respectively0, 1:1.2, 1:1.4, 1:1.6, 1:1.8, 1:2.0, 1:2.5, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1: 10. Fluorescence emission spectroscopy data studies show that: with Fe in solution3+The concentration is increased continuously, when the concentration is increased from 0 to 0.6 times, the maximum fluorescence emission of the fluorene fluorescent dye near 370 nm is obviously enhanced and is increased to 9.8 times; increase of Fe3+The amount of substance increased from 0.8 to 7-fold, and its strong fluorescence emission was quenched; continuing to increase Fe3+Even up to 10-fold, with little change in fluorescence emission; shows that the fluorene fluorescent dye can treat Fe with different concentrations in 5 percent methanol water solution3+Has dynamic 'off-on-off' double-conversion fluorescent signal detection potential.
Example 6
Ultraviolet and fluorescent properties of different metal ions in 5% aqueous methanol: respectively adding Li into a mixed solvent of methanol and water with the volume ratio of 95:5+、Na+、K+、Ba2+、Ca2+、Mg2+、Co2+、Hg2+、Mn2+、Ni2+、Cd2+、Zn2+、Al3+、Fe3+After the metal ions are subjected to plasma treatment, the fluorescence emission spectrum of the metal ions is not changed.

Claims (2)

1. Fe in dynamic monitoring water3+The molecular structure of the fluorescent dye is as follows:
Figure DEST_PATH_IMAGE002
。
2. the method of claim 1, wherein the Fe in water can be dynamically monitored3+The fluorescent dye is characterized in that imine groups in dye molecules are conjugated bridging groups of fluorene and phenyl and are complexing sites of metal ions, and the imine groups and Fe3+Resulting in a sensitive "off-on-off" dual-conversion fluorescence detection signal after complexation, for Fe3+Has the functions of quantitative and qualitative detection.
CN202111459325.2A 2021-12-02 2021-12-02 Fe in dynamic monitoring water3+Fluorescent dye and application thereof Withdrawn CN114105816A (en)

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CN202111459325.2A CN114105816A (en) 2021-12-02 2021-12-02 Fe in dynamic monitoring water3+Fluorescent dye and application thereof
LU501538A LU501538B1 (en) 2021-12-02 2022-02-23 FLUORESCENT DYE CAPABLE OF DYNAMICALLY MONITORING Fe3+ IN WATER AND APPLICATION THEREOF

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