LU501426B1 - MOLECULAR SENSOR CAPABLE OF DETECTING Cu2+ AND Zn2+ IN WATER AND USE THEREOF - Google Patents
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Abstract
The present disclosure provides a molecular sensor capable of detecting Cu2+ and Zn2+ in water and use thereof, and relates to the technical field of organic functional material detection. In the present disclosure, the provided molecular sensor is prepared by using 1,1,7,7-tetramethyl- 8-hydroxy-9-formyljulolidine and p-phenylenediamine as reaction raw materials through one- step polymerization; the molecular sensor includes three ion action sites: rigid aliphatic cycloalkylamino, imine and hydroxyl, and a dual-site coordination from the imine and ortho- phenolic hydroxyl has a relatively strong coordination ability to metal ions, such that the sensor can exhibit sensitive fluorescence decrease and increase detection signals for both Cu2+ and the Zn2+ ions. The molecular sensor has high sensitivity, desirable selectivity and significant values for use; and a preparation method of the molecular sensor has the advantages of high yield, simple synthesis process and easy implementation, which creates favorable conditions for industrial promotion and application of the molecular sensor.
Description
MOLECULAR SENSOR CAPABLE OF DETECTING Cu?" AND Zn?" IN WATER AND! 420
[01] The present disclosure relates to the technical field of organic material function detection, in particular to a molecular sensor capable of sensitively detecting Cu?* and Zn?" ions in water and use thereof.
[02] Agriculture is the source of human food and clothing, the foundation of survival, and the primary condition for all production. Without agriculture that provides cereals and necessary foods, lives and production can be adversely affected, and the country will lose the foundation for self-reliance. Soil and water are the foundation of agricultural development. With the rapid development of global economy, the water pollution, especially heavy metal pollution in water resources, 1s becoming increasingly serious. Heavy metal pollution has concealment, persistence, accumulation and irreversibility. In addition, heavy metals are highly toxic and easy to be accumulated and expanded by the biological chain. Therefore, the heavy metal pollution in water has largely endangered the ecological environment and human survival and development. The land is irrigated using sewage with a heavy metal content exceeding the standard, which will lead to a decline of crop yield and quality, and even withering and death. Moreover, the heavy metals entering the soil cannot disappear or be decomposed, and are easily absorbed by organisms to cause food pollution. When humans ingest water and foods containing high-content heavy metal ions, these heavy metal ions cannot be metabolized or degraded by human body, and will be accumulated to a certain degree, causing a series of diseases such as chronic poisoning, low immunity, dysfunction and cancers, and even life-threatening on humans. For example, Cu is an essential trace element for animals, plants and humans, and a small amount of the Cu can promote the growth of animals and plants; but a certain amount of Cu?" accumulated in the organisms may cause metabolic disorders, liver cirrhosis, liver ascites and even more serious symptoms. Zinc is an important element involved in immune function; but excessive zinc can inhibit the activity and bactericidal power of phagocytes, reduce human immune function, and weaken disease resistance to increase susceptibility to diseases. Therefore, it is of great significance to develop a rapid, convenient and sensitive detection method for heavy metal ions in water to the fields such as industrial and agricultural production and environmental science.
[03] At present, in the field of heavy metal ion detection in water, technologies such as inductively coupled plasma method, atomic fluorescence spectrometry and atomic absorption 1 spectrometry have been widely used. However, these detection methods generally require 501426 samples after special treatments, and have time-consuming detection. Fluorescence molecular sensors transform molecular recognition information that occurs in the microworld into easy-to- detect optical signals through clever designs, realizing real-time detection at the molecular level. The fluorescence molecular sensors have high sensitivity, desirable selectivity and easy operation, and are more widely used in the field of detection. People have developed numerous metal ion fluorescence molecular sensors with different functions based on different optical signal conversion mechanisms. However, most fluorescence molecular sensors currently only show sensitive detection functions for a specific metal ion, with relatively single functions. Therefore, these molecular fluorescence sensors have a relatively limited use, which is difficult to meet the growing market demand.
[04] Julolidine group, due to a highly-conjugated rigid coplanar structure, desirable optical properties and strong complexing performance to metal ions, is an excellent molecular sensor building unit [T. G Jo, Y. J. Na,* J. J. Lee, M. M. Lee, S. Y. Lee, C. Kim, New J. Chem., 2015, 39, 2580]. An enol tautomerism between an imine group and an ortho-phenolic hydroxyl of a Schiff base compound can increase the sensitivity of the molecular sensor, causing an ultra- sensitive spectral signal change after the molecular sensor interacts with the metal ions [J. Zhang, Z. Zhao, H. Shang, Q. Liu, F. Liu, New J. Chem., 2019, 43, 14179]. However, currently a fluorescence molecular sensor has not been developed yet, which is constructed by tetramethyl julolidine-phenylenediamine and can detect Cu?" and Zn?" ions in water.
[05] The technical objective of the present disclosure is to provide a tetramethyl julolidine- phenylenediamine fluorescence molecular sensor that has different optical detection signals for Cu?" and Zn?" ions and is easy to be prepared.
[06] Another technical objective of the present disclosure is to provide a method capable of sensitively detecting Cu?" and Zn?" ions in different types of water. The method is rapid, simple and easy to operate.
[07] To achieve the above objective, the present disclosure adopts the following technical solutions.
[08] A tetramethyl julolidine-phenylenediamine fluorescence molecular sensor that has different optical detection signals for Cu?* and Zn?" ions is provided, where the molecular sensor has a molecular structure as follows: 2
| hi N 7
[09]
[10] A preparation method of the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor that has different optical detection signals for Cu?" and Zn?* ions includes the following steps:
[11] Adding a mmol of 1,1,7,7-tetramethyl-8-hydroxy-9-formyljulolidine into a round bottom flask containing B mL of absolute ethanol, heating to reflux, adding 6 mmol of p- phenylenediamine and y ul of glacial acetic acid sequentially; continuing to react for 3-5 h; filtering an obtained mixture, washing with absolute ethanol, and drying to obtain a yellow- brown tetramethyl julolidine-phenylenediamine fluorescence molecular sensor; where a: B: y: 6 is 2:25:1:200.
[12] A preparation reaction formula of the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor is as follows:
OH OH G + ell Hi Les Ho EtOH, Reflux, N 7 ud
[13]
[14] The present disclosure has the following technical effects: the tetramethyl julolidine- phenylenediamine fluorescence molecular sensor includes three ion action sites: rigid aliphatic cycloalkylamino, imine and hydroxyl, and a dual-site coordination from the imine and ortho- phenolic hydroxyl has a relatively strong coordination ability to metal ions, such that the sensor can exhibit significantly different optical detection signals for the Cu?* and the Zn?" ions. The molecular sensor has high sensitivity, rapid response and relatively high values for use; and a preparation method of the molecular sensor has high yield, mild synthesis conditions and simple preparation process, which creates favorable conditions for industrial promotion and use of the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor.
[15] FIG. 1 is a hydrogen nuclear magnetic resonance (NMR) spectrum of compounds obtained in Examples 1-2;
[16] FIG. 2 shows a fluorescence emission performance of a tetramethyl julolidine- phenylenediamine fluorescence molecular sensor in a 95% dimethyl sulfoxide (DMSO) distilled 3 aqueous solution added with different metal ions; HUS01420
[17] FIG. 3 shows a fluorescence emission performance of the tetramethyl julolidine- phenylenediamine fluorescence molecular sensor in a 95% dimethylformamide (DMF) distilled aqueous solution added with different metal ions; and
[18] FIG. 4 shows a fluorescence emission spectrum of the tetramethyl julolidine- phenylenediamine fluorescence molecular sensor in the 95% DMSO distilled aqueous solution added with 10 times Zn?*/Cu?* and other different metal ions.
[19] A tetramethyl julolidine-phenylenediamine fluorescence molecular sensor that has different optical detection signals for Cu?* and Zn?" ions is provided, which the molecular sensor has a molecular structure as follows: Hd
[20] ;
[21] The molecular sensor is prepared by using 1,1,7,7-tetramethyl-8-hydroxy-9- formyljulolidine and p-phenylenediamine as reaction raw materials through one-step polymerization, where a synthesis reaction formula is as follows: OH oH EtOH, Reftux. N 7 ud
[22]
[23] Example 1
[24] Preparation of a compound A: 2 mmol of 1,1,7,7-tetramethyl-8-hydroxy-9- formyljulolidine was added into a round bottom flask containing 25 mL of absolute ethanol, heated to reflux, 1 mmol of p-phenylenediamine and 200 pL of glacial acetic acid were added sequentially; reaction was continued for 3 h; an obtained mixture was filtered, washed with absolute ethanol, and dried to obtain a yellow-brown compound A with a mass of 295.8 mg, where a yield was 47.8%.
[25] Example 2
[26] Preparation of a compound B: 2 mmol of 1,1,7,7-tetramethyl-8-hydroxy-9- formyljulolidine was added into a round bottom flask containing 25 mL of absolute ethanol, heated to reflux, 1 mmol of p-phenylenediamine and 200 pL of glacial acetic acid were added sequentially; reaction was continued for 5 h; an obtained mixture was filtered, washed with 4 absolute ethanol, and dried to obtain a yellow-brown compound A with a mass of 296.4 mg 0 +20 where a yield was 48%.
[27] The compounds A and B obtained in Examples 1 and 2 were analyzed and determined, respectively. The two compounds had consistent hydrogen NMR spectra, and specific data was as follows: in 'H NMR (CDCIs, 400 MHz), there were 2 OH proton signal peaks: 13.51 (s, 2H); there were 2 C=N-carbon proton signal peaks: 8.33 (s, 2H); there were 6 aromatic ring proton signal peaks: 7.02 (m, 4H ), 6.74 (s, 2H); there were 16 CH,-proton signal peaks: 3.24 (d, 8H),
1.96 (d, 8H); and there were 24 CHz-proton signal peaks: 1.33 (s, 12H), 1.26 (s, 12H). This result is basically the same as a theoretical value of a tetramethyl julolidine-phenylenediamine fluorescence molecule. From this result, it can be confirmed that the compounds A and B have a molecular structure as follows: À Hs N 7
[28] , namely the tetramethyl julolidine- phenylenediamine fluorescence molecule.
[29] Example 3
[30] Fluorescence detection performance of a tetramethyl julolidine-phenylenediamine fluorescence molecular sensor for different metal ions in 95% DMSO distilled aqueous solution was determined: in 95% DMSO distilled aqueous solution, a tetramethyl julolidine- phenylenediamine fluorescence molecular sensor with a concentration of 1x10” mol/L has a maximum fluorescence emission peak at 543 nm; after 10 times equivalent of Zn?" were added, the maximum fluorescence emission intensity at 543 nm was increased by 2.4 times; after Cu?” was added, the maximum fluorescence emission peak at 543 nm was almost quenched; and after other metal ions such as Al**, Fe, Hg?", Co”, Mn?*, Ni?*, Cd?*, Li”, Na’, K*, Ba?*, Ca?" and Mg?* were added, the maximum fluorescence emission of the compound molecule at 543 nm had almost no obvious change. These data indicate that the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor has significantly different fluorescence signal responses to the Cu?" and the Zn?" ions, and has a potential to recognize these two metal ions.
[31] Example 4
[32] Fluorescence detection performance of a tetramethyl julolidine-phenylenediamine fluorescence molecular sensor for different metal ions in 95% DMF distilled aqueous solution was determined: in 95% DMF distilled aqueous solution, a tetramethyl julolidine- phenylenediamine fluorescence molecular sensor with a concentration of 1x10 mol/L has a maximum fluorescence emission peak at 540 nm; after 10 times equivalent of Zn?* were added." 426 the maximum fluorescence emission intensity at 540 nm was increased by 9.5 times; after Cu?” was added, the maximum fluorescence emission peak at 540 nm was almost quenched; and after other metal ions such as Al**, Fe, Hg?", Co”, Mn?*, Ni?*, Cd?*, Li”, Na’, K*, Ba?*, Ca?" and Mg?* were added, the maximum fluorescence emission of the compound molecule at 540 nm had almost no obvious change. These data indicate that the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor has different fluorescence recognition potentials for Cu?” and Zn?" ions.
[33] Example 5
[34] Selective competition of a tetramethyl julolidine-phenylenediamine fluorescence molecular sensor for Zn?*/Cu?* and other metal ions was determined: 10 times equivalent of Zn?" and other metal ions such as Al**, Fe**, Hg?", Co?*, Mn?*, Ni?*, Cd?*, Li”, Na*, K*, Ba?*, Ca?" and Mg?" were added to 95% DMSO aqueous solution of tetramethyl julolidine- phenylenediamine fluorescence molecular sensor with a concentration of 1x10 mol/L. A fluorescence emission spectrum study of a mixed system shows that: after 10 times the equivalent of Zn?" are added to the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor, the fluorescence emission at 543 nm is enhanced; when metal ions such as APT, Fe**, Hg”, Co?*, Mn?*, Ni?*, Cd”*, Li*, Na”, K*, Ba?*, Ca” and Mg?" and the Zn?" are added to the solution of the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor at the same time, the fluorescence emission spectrum of the mixed system is close to that of tetramethyl julolidine-phenylenediamine fluorescence molecular sensor-Zn?* system. Similarly, when 10 times the equivalent of Cu?" and other metal ions such as A1**, Fe**, Hg?*, Co”, Mn?*, Ni?*, Cd”*, Li", Na”, K*, Ba”, Ca?" and Mg?" are added to the solution of the tetramethyl julolidine-phenylenediamine fluorescence molecule, the fluorescence of the mixed system is similar to that of a tetramethyl julolidine-phenylenediamine fluorescence molecular sensor-Cu”” system. These indicate that even when the Zn?* and Cu?* coexist with the above other metal ions, the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor still exhibits a desirable selective detection performance sensor on the Zn?" and Cu”.
[35] Example 6
[36] An actual detection performance of a tetramethyl julolidine-phenylenediamine fluorescence molecular sensor for Cu?” and Zn?" ions in river water and tap water was determined: a river water sample from the Tuhai River in the Dezhou area and a tap water sample were collected, suspended solids were removed by membrane pretreatment, and the water samples were determined to be free of Cu?" and Zn?" by atomic absorption spectrometry; Mg”, Ca?*, Li*, Na* and K* (10.00 uM) were added to the water samples to prepare synthetic 6 water; different amounts of Cu? and Zn?" were added to the synthetic water, and à 501426 reproducibility was calculated by fluorescence test. The results are shown in the table below, the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor has a reproducibility on Cu?" of 101-102%, and a reproducibility on Zn?* of 99-102%, within an allowable error range. It shows that the tetramethyl julolidine-phenylenediamine fluorescence molecular sensor has a relatively high accuracy for the analysis and detection of the Cu?" and the Zn?* in actual water samples, with wide prospects for use.
[37] Table 1 Actual detection performance of tetramethyl julolidine-phenylenediamine fluorescence molecular sensor for Cu?* and Zn?" ions in tap water or river water
[38] Water sample Addition of Cu? (M) _ Detection of Cu?” (M) Reproducibility (%) R.S.D.2 (%) River water - - Synthetic water 1° 1.0 x 106 (1.02 + 0.02) x 10° 102 2.0 Synthetic water 2° 1.0 x 105 (1.01 + 0.06) x 10- 101 1.0 Synthetic water 3° 1.0 x 10+ (1.01 £0.05) x 10 101 1.0 Addition of Zn”* (M) Detection of Zn”* (M) Reproducibility (%) _ R.S.D.* (%) Tap water -- -- Synthetic water 1° 1.0 x 106 (1.01 £0.10) x 1076 101 1.0 Synthetic water 2° 1.0 x 107 (1.02 + 0.06) x 105 102 2.0 Synthetic water 3° 1.0 x 10# (0.99 + 0.05) x 10 99 1.0
[39] 2 n=3; ° river water or tap water with Mg”, Ca?*, Li", Na” and K* (10.00 uM), test conditions are: 10 uM tetramethyl julolidine-phenylenediamine fluorescence molecular sensor in a mixed solvent of DMF-river water/tap water (19:1). 7
Claims (2)
1. A molecular sensor capable of detecting Cu?" and Zn?" in water, wherein the molecular sensor has a molecular structure as follows: OH 2
N \ gl O "
HO
2. Use of the molecular sensor capable of detecting Cu?* and Zn?* in water according to claim 1, wherein the molecular sensor comprises three ion action sites: rigid aliphatic cycloalkylamino, imine and hydroxyl, and a dual-site coordination from the imine and ortho- phenolic hydroxyl has a relatively strong coordination ability to metal ions, such that the sensor can exhibit sensitive fluorescence decrease and increase detection functions for the Cu?” and the Zn?" in different types of water.
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