Diacylhydrazone derivative containing long-chain alkyl, fluorescent supramolecular gel and application of fluorescent supramolecular gel in detection of aluminum ions
By developing bisylhydrazone derivatives containing long-chain alkyl groups as small-molecular gelling agents and fluorescent probes, a fluorescent supramolecular gel that induces fluorescence enhancement is formed, which solves the problem of low sensitivity for detection of aluminum ions in the prior art, and realizes trace detection of aluminum ions.
Patent Information
- Application Number
- CN202411966596.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-30
- Publication Date
- 2025-04-04
AI Technical Summary
In the prior art, the fluorescent probe of aluminum ions is not very sensitive and the detection range is limited, making it difficult to detect trace amounts of aluminum ions.
A long-chain alkyl-containing bisacryl derivative was developed as a small molecule gelling agent to form a fluorescent supramolecular gel that induces fluorescence enhancement, and the bisacryl derivative was used as a fluorescence probe to quantitatively analyze aluminum ions.
The trace detection of aluminum ions is realized, with a wide detection range and high detection sensitivity. It can conduct quantitative detection of Al3+ within the concentration range of 10-9 to 10-5 mol/L, and is not disturbed by other metal ions.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of supramolecular gelling agents and fluorescence detection, and specifically relates to a bisacylhydrazone derivative containing a long-chain alkyl group, and a fluorescent supramolecular gel with gelation-induced fluorescence enhancement based on the bisacylhydrazone derivative. The bisacylhydrazone derivative is used as a fluorescent probe to quantitatively analyze aluminum ions, thereby realizing trace detection of aluminum ions. Background Art
[0002] Supramolecular chemistry is the study of weak interactions between molecules and molecular assembly. It emphasizes the construction of supramolecular systems with specific structures and functions, thus opening up a new path for the development of molecular devices, materials science and life sciences, and providing an important direction for the development of chemistry in the 21st century. Small molecule gels formed by gelling appropriate solvents with small molecule organic compounds are such a new type of supramolecular functional materials with great development potential. These small molecule organic compounds are called low-molecule-mass gelators (LMMGs).
[0003] Small molecule gels formed by self-assembly of small molecule gelling agents in solvents through weak intermolecular interactions (including hydrogen bonds, van der Waals interactions, electrostatic interactions, π-π stacking interactions, dipole interactions, etc.) generally have thermal reversible properties; in addition, by introducing different functional groups into the structure of small molecule gelling agents through chemical synthesis methods, the formed gels can also show responsiveness to external stimuli such as light, sound, electricity, pH, shear force, and chemical substances. Therefore, they show great application potential in controlled release, tissue culture, gentle separation, molecular material template synthesis, gel propellant preparation, information storage and perception, and supramolecular device preparation.
[0004] Compounds with various structural characteristics can be used as small molecule gelling agents, such as fatty acid derivatives, amino acid derivatives, amine derivatives, cholesteric derivatives, etc. Aromatic acylhydrazone is a class of Schiff base compounds, which are formed by the condensation of aldehydes and hydrazides, and have also received extensive attention in gel materials. On the one hand, since acylhydrazone has the ability to repair hydrogels without external stimulation, people use it as a structural fragment of the polymer to construct self-healing covalent hydrogels. On the other hand, due to the excellent coordination ability of acylhydrazone, it can be used as an organic ligand to prepare metal gels through coordination with various metal ions. However, the use of acylhydrazone itself as a small molecule gelling agent to form supramolecular gels is very rare. Due to the characteristics of the acylhydrazone compound itself, the supramolecular gel formed by acylhydrazone derivatives as small molecule gelling agents will have catalytic, analgesic, anti-inflammatory, antibacterial, anticancer and other properties, which will greatly expand the application field of supramolecular gels.
[0005] Fluorescence sensors have developed rapidly in recent years due to their high sensitivity, rich signal acquisition, ease of use, and relatively mature instrument design. A large number of fluorescence sensors have been developed and widely used in various fields such as biology, physiology, pharmacology, and environmental science, achieving sensitive detection of a variety of analytes such as cations, anions, neutral molecules, and biomacromolecules. Aluminum is widely used in many fields of social life, such as papermaking, food additives, textile industry, and alloy production. However, when aluminum ions are deposited in the body through food, they can cause serious health diseases, such as Alzheimer's disease, Parkinson's disease, and hemodialysis encephalopathy. Therefore, the development of highly sensitive and highly selective aluminum ion probes is of great significance for environmental and health detection. Although many aluminum ion fluorescent probes have been reported, it is still a very challenging task to develop aluminum ion fluorescent probes with high sensitivity, high selectivity, wide linear range, extremely low detection limit, and low dosage.
[0006] Wang et al. (An acylhydrazone-based AIE organogel for the selective sensing of submicromolar level Al 3+ and Al(III)-based metallogel formation to detect oxalic acid.New J.Chem.,2021,45,1899-1903) reported a triacylhydrazone derivative with aggregation-induced fluorescence enhancement, which can gel DMF and detect Al(III)-based metallogel formation to detect oxalic acid. 3+ , the detection limit is 8.702×10 -7 mol / L. However, the triacylhydrazone derivatives reported in this report have a rigid structure and can only gel DMF. 3+ Therefore, the development of diacylhydrazone or polyacylhydrazone derivatives with flexible substituents is of great significance for regulating the self-assembly ability of acylhydrazone derivatives and developing fluorescent probes with higher performance. Summary of the invention
[0007] The invention aims to provide a bisacylhydrazone derivative containing a long-chain alkyl group, and a method for preparing a fluorescent supramolecular gel with gelation-induced fluorescence enhancement by using the bisacylhydrazone derivative as a small molecule gelling agent, and at the same time using the bisacylhydrazone derivative as a fluorescent probe to quantitatively analyze aluminum ions and realize trace detection of aluminum ions.
[0008] The structural formula of the long-chain alkyl-containing bisacylhydrazone derivative provided by the present invention is as follows:
[0009]
[0010] Where C n H 2n+1 Represents C 10 ~C 18 A straight chain alkyl group, R represents Any one of .
[0011] The synthetic route and specific synthetic method of the above-mentioned long-chain alkyl-containing bisacylhydrazone derivatives are as follows:
[0012]
[0013] 1. Preparation of compound of formula I
[0014] Add anhydrous potassium carbonate and dimethyl 5-hydroxyisophthalate to DMF, raise the temperature to 65°C, and then add 1-bromoalkane C n H n+1 -Br, dimethyl 5-hydroxyisophthalate and 1-bromoalkane C n H n+1 -Br, anhydrous potassium carbonate in a molar ratio of 1:1-3:1-3, the temperature is raised to 80°C for reaction for 9 hours, distilled water is added after the reaction is completed, and the mixture is cooled in an ice water bath for 30 minutes, the obtained mixture is filtered, and the obtained solid is recrystallized with acetone to obtain a compound of formula I.
[0015] 2. Preparation of compound of formula II
[0016] The compound of formula I is dissolved in anhydrous ethanol, and a hydrazine hydrate aqueous solution with a mass concentration of 80% is added, and the molar ratio of the compound of formula I to hydrazine hydrate is 1:2-10. The temperature is raised to 80°C and refluxed for reaction for 10-24 hours. After the reaction is completed, the temperature is lowered to room temperature, distilled water is added, and the mixture is filtered and washed to obtain a compound of formula II.
[0017] 3. Preparation of diacylhydrazone derivatives containing long-chain alkyl groups
[0018] The aromatic aldehyde R-CHO is dissolved in anhydrous ethanol, and then a compound of formula II is added, wherein the molar ratio of the compound of formula II to the aromatic aldehyde R-CHO is 1:1-4, and the mixture is heated to reflux and reacted for 10 hours. After the reaction is completed, the mixture is cooled to room temperature, filtered, and the solid is hot-washed with anhydrous ethanol to obtain a bisacylhydrazone derivative III containing a long-chain alkyl group.
[0019] The fluorescent supramolecular gel provided by the present invention is a gel formed by the above-mentioned bisacylhydrazone derivative containing a long-chain alkyl group in an organic solvent, wherein the mass-volume ratio of the bisacylhydrazone derivative containing a long-chain alkyl group to the organic solvent is 0.7-30 mg:1 mL, and preferably the mass-volume ratio of the bisacylhydrazone derivative containing a long-chain alkyl group to the organic solvent is 15-25 mg:1 mL.
[0020] The organic solvent is any one of methanol, n-propanol, dichloromethane, chloroform and benzene.
[0021] The preparation method of the fluorescent supramolecular gel is as follows: dissolving a diacylhydrazone derivative containing a long-chain alkyl group in an organic solvent by heating, and then cooling the mixture at room temperature to obtain a luminescent supramolecular gel with enhanced gelation-induced fluorescence.
[0022] The long-chain alkyl-containing diacylhydrazone derivatives of the present invention can be used as fluorescent probes for selective detection of Al 3+ .
[0023] The beneficial effects of the present invention are as follows:
[0024] 1. The present invention introduces flexible long-chain alkyl groups with different lengths into the molecular structure of bisacylhydrazone, and synthesizes bisacylhydrazone derivatives having weak interaction sites such as hydrogen bonding, π-π stacking and van der Waals, which can synergistically utilize multiple weak interactions to enhance the self-assembly ability of acylhydrazone derivatives and greatly increase their aggregation-induced fluorescence enhancement performance.
[0025] 2. The long-chain alkyl-containing bisacylhydrazone derivative of the present invention has the property of aggregation-induced fluorescence enhancement. In a mixed solvent of methanol and water, its fluorescence intensity changes significantly with the increase of the volume content of water, and the emission wavelength gradually red-shifts with the increase of the volume content of water. When the volume content of water is 50%, the fluorescence intensity reaches the maximum value; when the volume content of water is 100%, the emission wavelength red-shifts to the maximum value.
[0026] 3. The long-chain alkyl-containing bisacylhydrazone derivatives of the present invention can form fluorescent supramolecular gels in a variety of organic solvents. The gels have gelation-induced fluorescence enhancement properties. The fluorescence intensity of the system before and after gelation is significantly enhanced. The fluorescence intensity after gelation is 50 to 200 times that before formation.
[0027] 4. Add 0.2 to 2.0 equivalents of Al to the methanol solution of the long-chain alkyl-containing bisacylhydrazone derivative of the present invention. 3+ After that, the fluorescence emission of the system is enhanced by 1 to 50 times, and the fluorescence intensity of the system is related to the Al 3+ The concentration showed a good linear relationship, and it could be -9 ~10 -5 mol / L concentration range for Al 3+ Quantitative detection. Common metal ions such as Zn 2+ 、Na + , Ca 2+ Mg 2 + 、Ag + , Cu 2+ 、Co 2+ 、Ni 2+ , Fe3+ , Fe 2+ , Pb 3+ 、Ce 3+ After adding, it will not cause interference, the detection range is wide, the detection sensitivity is high, reaching Al 3+ Trace detection. BRIEF DESCRIPTION OF THE DRAWINGS
[0028] Figure 1 This is the H NMR spectrum of the long-chain alkyl-containing bisacylhydrazone derivative III-1 prepared in Example 1.
[0029] Figure 2 This is a dimer structure diagram of the long-chain alkyl-containing bisacylhydrazone derivative III-1 prepared in Example 1.
[0030] Figure 3 This is a one-dimensional chain structure diagram of the long-chain alkyl-containing bisacylhydrazone derivative III-1 prepared in Example 1.
[0031] Figure 4 This is the H NMR spectrum of the long-chain alkyl-containing bisacylhydrazone derivative III-2 prepared in Example 2.
[0032] Figure 5 These are photographs of the long-chain alkyl-containing bisacylhydrazone derivative III-1 in methanol-water with different water volume contents under ultraviolet light.
[0033] Figure 6 It is the fluorescence emission spectrum of the bisacylhydrazone derivative III-1 containing a long-chain alkyl group in methanol-water with different volume contents of water.
[0034] Figure 7 This is a curve showing the change in fluorescence emission intensity of the long-chain alkyl-containing bisacylhydrazone derivative III-1 in methanol-water versus the volume content of water.
[0035] Figure 8 These are photographs of the long-chain alkyl-containing bisacylhydrazone derivative III-2 under ultraviolet light in methanol-water with different water volume contents.
[0036] Fig. 9 It is the fluorescence emission spectrum of the long-chain alkyl-containing bisacylhydrazone derivative III-2 in methanol-water with different volume contents of water.
[0037] Fig.10 This is a curve showing the change in fluorescence emission intensity of the long-chain alkyl-containing bisacylhydrazone derivative III-2 in methanol-water versus the volume content of water.
[0038] Fig.11 This is a photograph of the luminescent supramolecular gel with gelation-induced fluorescence enhancement prepared in Example 3.
[0039] Fig.12This is a scanning electron microscope photograph of the gel prepared in Example 3 after freeze drying.
[0040] Fig.13 This is a photograph of the luminescent supramolecular gel with gelation-induced fluorescence enhancement prepared in Example 4.
[0041] Fig.14 This is a scanning electron microscope photograph of the gel prepared in Example 4 after freeze drying.
[0042] Fig.15 yes Fig.14 A partial enlarged view of .
[0043] Fig.16 1 is the fluorescence emission spectrum of the gel prepared in Example 5 at different times during the formation process.
[0044] Fig.17 These are photos of the gel prepared in Example 5 at different times during its formation.
[0045] Fig.18 This is a photograph of the long-chain alkyl-containing bisacylhydrazone derivative III-1 under ultraviolet light in a methanol solution containing different metal ions.
[0046] Fig.19 This is a photograph of the long-chain alkyl-containing bisacylhydrazone derivative III-2 under ultraviolet light in a methanol solution containing different metal ions.
[0047] Fig. 20 Containing different concentrations of Al 3+ Fluorescence spectrum of methanol solution of long-chain alkyl-containing bisacylhydrazone derivative III-1.
[0048] Fig.21 Containing different concentrations of Al 3+ The fluorescence intensity of the methanol solution of the long-chain alkyl-containing bisacylhydrazone derivative III-1 increases with the concentration of Al 3+ Linear fitting results of concentration changes. DETAILED DESCRIPTION
[0049] The present invention is further described in detail below with reference to the accompanying drawings and embodiments, but the present invention is not limited to these embodiments.
[0050] Example 1
[0051]
[0052] 1. Preparation of compound of formula Ⅰ-1
[0053] Add 35mL DMF, 6.0g (43.4mmol) anhydrous potassium carbonate, and then add 6.30g (30mmol) 5-hydroxyisophthalic acid dimethyl ester in a three-necked flask, heat to 65°C, then add 8.21mL (34.28mmol) 1-bromododecane, heat to 80°C and react for 10 hours. After the reaction, add 1000mL distilled water, cool in an ice water bath for 30 minutes, filter the obtained mixture, and recrystallize the obtained solid twice with acetone to obtain the compound of formula Ⅰ-1. The structural characterization data of the compound of formula Ⅰ-1 are: 1 HNMR (400MHz, CDCl 3 ):δ=8.24(s,1H,benzene ring),7.72(s,2H,benzene ring),4.06(t,2H,-CH 2 -O-Ar), 3.89(s,6H,-CH 2 -O-OCH), 1.78(m,2H,-CH 2 ),1.55(m,2H,-CH 2 ),1.25(m,16H,-C 8 H 16 ),0.86(t,3H,-CH 3 ).
[0054] 2. Preparation of compound of formula II-1
[0055] Add 35mL of anhydrous ethanol and 3.778g (0.01mol) of the compound of formula Ⅰ-1 to a three-necked flask, then add 2mL (0.03mol) of 80% hydrated hydrazine aqueous solution, heat to 80°C to condense and reflux, and react for 24 hours under condensation and reflux. After the reaction is completed, cool to room temperature, add 30mL of distilled water, stir, and filter the obtained mixture. Rinse the filter cake with a large amount of water and then with ethanol to obtain the compound of formula Ⅱ-1. The structural characterization data of the compound of formula Ⅱ-1 are: 1 H NMR (400 MHz, DMSO-d 6 ):δ=9.78(s,2H,-NH),7.84(s,1H,benzene ring),7.45(s,2H,benzene ring),4.53(s,4H,-NH 2 ),4.02(t,2H,-CH 2 ),1.71(m,2H,-CH 2 ),1.42(m,2H,-CH 2 ),1.23(m,16H,-C 8 H 16 ),0.84(t,3H,-CH 3 ).
[0056] 3. Preparation of long-chain alkyl-containing bisacylhydrazone derivatives III-1
[0057] In a three-necked flask, 100 mL of anhydrous ethanol and 2.24 mL (0.021 mol) of salicylaldehyde were added, and then 2.65 g (0.007 mol) of the compound of formula II-1 were added, and the mixture was heated to reflux. After reacting for 10 hours, the mixture was poured into a beaker, cooled to room temperature, and filtered. The solid obtained by filtration was hot-washed with anhydrous ethanol 4 times to obtain a long-chain alkyl-containing bisacylhydrazone derivative III-1, whose structural characterization data are as follows: 1 H NMR (400 MHz, DMSO-d 6 ):δ=12.21(s,2H,-NH),11.21(s,2H,-OH),8.69(s,2H,-CHN),8.11(s,1H,benzene ring),7.69(s,2H,benzene ring),7.57(d,2H,benzene ring),7.32(t,2H,benzene ring),6.95(t,4H,benzene ring),4.14(t,2H,-CH 2 O), 1.78(m,2H,-CH 2 ),1.48(m,2H,-CH 2 ),1.25(m,16H,-C 8 H 16 ),0.84(t,3H,-CH 3 ), H NMR spectrum Figure 1 ; HRMS (ESI, m / z) C 34 H 42 N 4 O 5 : Theoretical value [(M+H) + ]:587.3233; measured value:587.3238.
[0058] 20 mg of the bisacylhydrazone derivative III-1 was dissolved in 1 mL of a mixed solvent of methanol-DMSO and allowed to stand for about a week to form a block single crystal of the bisacylhydrazone derivative III-1. After single crystal X-ray crystal structure determination and analysis, the crystal of the bisacylhydrazone derivative III-1 was obtained. The crystal formed by the bisacylhydrazone derivative III-1 is a monoclinic system with a space group of P2 / c and unit cell parameters of: α=90°,β=107.216(5)°,γ=90°. The two molecules of diacylhydrazone derivative III-1 form a dimer structure through intermolecular hydrogen bonds (see Figure 2 ), methanol molecules bridge two adjacent dimers through hydrogen bonds to form a one-dimensional chain structure (see Figure 3 ), two adjacent dimers are perpendicular to each other.
[0059] Example 2
[0060]
[0061] In step 3 of this example, salicylaldehyde in step 3 of example 1 is replaced by 1-hydroxy-2-naphthaldehyde in an equal mole ratio, and the other steps are the same as those in example 1 to obtain a bisacylhydrazone derivative III-2 containing a long-chain alkyl group, the structural characterization data of which are as follows: 1 HNMR: (DMSO-d 6 / Me 4 Si, 400Hz): δ(ppm)=12.88(s, 2H, -NH), 12.44(s, 2H, -OH), 8.78(s, 2H, -N=CH), 8.33(d, 2H, naphthalene ring), 8.18(s, 1H, benzene ring), 7.90(d, 2H, naphthalene ring), 7.75(s, 2H, benzene ring), 7.61(t, 2H, naphthalene ring), 7.57(t, 2H, naphthalene ring), 7.55(t, 2H, naphthalene ring), 7.49(d, 2H, naphthalene ring), 4.16(t, 2H, -OCH 2 ),1.80(m,2H,-CH 2 ),1.48(m,2H,-CH 2 ),1.24(m,16H,-C 8 H 16 ),0.84(t,3H,-CH 3 ), H NMR spectrum Figure 4 ; HRMS (ESI, m / z) C 42 H 46 N 4 O 5 : Theoretical value [(M+H) + ]:687.3546; measured value:687.3547.
[0062] Methanol-water with water volume fractions of 0, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100% was selected as the solvent, and the test concentration was 1×10 -5 mol / L of the fluorescence emission of the long-chain alkyl-containing bisacylhydrazone derivative III-1 and the long-chain alkyl-containing bisacylhydrazone derivative III-2. The results are shown in Figures 5 to 10. As can be seen from the figure, when the volume content of water changes from 0 to 50%, the fluorescence emission intensity of the long-chain alkyl-containing bisacylhydrazone derivative III-1 increases from 16.574 to 66.836, and when the volume content of water changes from 50% to 100%, its fluorescence emission intensity decreases from 66.836 to 30.968, showing typical aggregation-induced fluorescence enhancement properties. The fluorescence intensity is the largest when the volume fraction of water is 50%, which increases by 4 times. When the volume content of water changes from 0 to 50%, the fluorescence emission intensity of the long-chain alkyl-containing bisacylhydrazone derivative III-2 increases from 13.666 to 422.24, and when the volume content of water changes from 50% to 100%, its fluorescence emission intensity decreases from 422.24 to 179.515, also showing typical aggregation-induced fluorescence enhancement properties. The fluorescence intensity is the largest when the volume fraction of water is 50%, which increases by more than 30 times.
[0063] Example 3
[0064] 20 mg of the long-chain alkyl-containing bisacylhydrazone derivative III-1 prepared in Example 1 was heated and dissolved in 1 mL of benzene to form a solution, which was then allowed to stand at room temperature for 5 minutes to obtain a fluorescent supramolecular gel, which exhibited the characteristics of a solid (see Fig.11 ), the dried gel was characterized by S-3400N II environmental scanning electron microscope, the results are shown in Fig.12 It can be seen that the benzene gel of the long-chain alkyl-containing bisacylhydrazone derivative III-1 forms an irregular lamellar structure.
[0065] Example 4
[0066] 20 mg of the long-chain alkyl-containing bisacylhydrazone derivative III-2 prepared in Example 2 was heated and dissolved in 1 mL of benzene to form a solution, which was then allowed to stand at room temperature for 5 minutes to obtain a fluorescent supramolecular gel, which exhibited the characteristics of a solid (see Fig.13 ), the dried gel was characterized by S-3400N II environmental scanning electron microscope, the results are shown in Fig.14 and Fig.15 It can be seen that the benzene gel of the long-chain alkyl-containing bisacylhydrazone derivative III-2 forms a large-sized lamellar structure, and the lamellar structure is formed by long fibers entangled together.
[0067] Example 5
[0068] 0.72 mg of the long-chain alkyl-containing bisacylhydrazone derivative III-2 prepared in Example 2 was heated and dissolved in 1 mL of benzene to form a solution, which was then allowed to stand at room temperature for 8 minutes to obtain a fluorescent supramolecular gel, which exhibited the characteristics of a solid. During the formation of the gel, its fluorescence emission gradually increased, and after the gel was fully formed, the fluorescence intensity increased by 200 times (see Fig.16 and Fig.17 ).
[0069] Example 6
[0070] The present invention contains a long-chain alkyl diacylhydrazone derivative for Al 3+ Selective recognition
[0071] Methanol was selected as the solvent and the concentration was 5×10 -6 mol / L methanol solution of long-chain alkyl-containing bisacylhydrazone derivative III-1 and methanol solution of long-chain alkyl-containing bisacylhydrazone derivative III-2, 13 metal ions were selected: Al 3 + 、Zn 2+ 、Na + , Ca 2+ Mg 2+ 、Ag + , Cu 2+ 、Co 2+ 、Ni 2+ , Fe 3+ , Fe 2+ , Pb 3+ 、Ce 3+ ; 13 kinds of metal ions were added to the methanol solution of the long-chain alkyl-containing bisacylhydrazone derivative III-1 and the methanol solution of the long-chain alkyl-containing bisacylhydrazone derivative III-2, respectively. After the addition, the concentration of each metal ion in the system was 1×10 -5 mol / L, and observe the fluorescence changes under ultraviolet light. The results are shown in Fig.18 and 19 As can be seen from the figure, only with the addition of Al 3+ The solution of ions emitted strong blue light, while other ions did not show obvious fluorescence.
[0072] At a concentration of 5×10 -6 Al was added to a methanol solution of a 1.5 mol / L long-chain alkyl-containing bisacylhydrazone derivative III-1. 3 + , so that Al 3+ The concentrations were 1×10 -6 , 2×10 -6 , 3×10 -6 , 4×10 -6 , 5×10 -6 , 6×10 -6 ,7×10 -6 , 8×10 -6 ,9×10 -6 , 1×10 -5 mol / L, test the fluorescence intensity of each system, and use the fluorescence intensity to compare Al 3+The concentration of Al was plotted and linear fitting was performed. Then the minimum detection limit was calculated according to the formula: LOD = 3σ / k, where LOD represents the ion detection limit and σ is the concentration without Al. 3+ The standard deviation of the fluorescence emission intensity of the system at the time of the test, k represents the slope of the fitted linear function. Fig. 20 and 21 As shown in the figure, the fluorescence intensity of the long-chain alkyl-containing bisacylhydrazone derivative III-1 changes with the Al 3+ The linear fitting equation is I = -33.25053 + 45.99437 [Al 3+ ]×10 -6 , where R 2 =0.99404, indicating that it has the accuracy standard as a fluorescent probe, Al 3+ The minimum detection limit was 4.79×10 -9 mol / L.
Claims
1. A diacylhydrazone derivative containing a long-chain alkyl group, characterized in that: The structural formula of the derivative is as follows: Where C n H 2n+1 Represents C 10 ~C 18 A straight chain alkyl group, R represents Any one of .
2. A fluorescent supramolecular gel, characterized in that: The fluorescent supramolecular gel is a gel formed by the long-chain alkyl-containing bisacylhydrazone derivative according to claim 1 in an organic solvent.
3. The fluorescent supramolecular gel according to claim 2, characterized in that: The mass-volume ratio of the long-chain alkyl-containing bisacylhydrazone derivative to the organic solvent is 0.7-30 mg:1 mL.
4. The fluorescent supramolecular gel according to claim 2, characterized in that: The mass-volume ratio of the long-chain alkyl-containing bisacylhydrazone derivative to the organic solvent is 15-25 mg:1 mL.
5. The fluorescent supramolecular gel according to any one of claims 2 to 4, characterized in that: The organic solvent is any one of methanol, n-propanol, dichloromethane, chloroform and benzene.
6. The long-chain alkyl-containing bisacylhydrazone derivative according to claim 1 is useful in detecting Al 3+ Uses in.