CN116410347A - 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe and preparation method and application thereof - Google Patents
2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe and a preparation method and application thereof. The method takes N-chitosan-4-hydrazino-1, 8-naphthalimide as a raw material and reacts with 1-naphthalene isothiocyanate to prepare 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide. Under 365nm ultraviolet light irradiation, the 2- (- (N-chitosan-based-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe solution does not emit fluorescence, and Hg is added to the probe solution 2+ After that, the fluorescent color of the solution is changed from colorless to bright yellow, and the solution is changed into Hg 2+ The detection limit of (2) reaches 7.3X10 ‑8 M, response time 5min, as detection Hg 2+ The fluorescent probe for ions has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fluorescence detection, and relates to a 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe and a preparation method and application thereof.
Background
The chitosan is an alkaline polysaccharide existing in the nature, is rich in source, safe and nontoxic, has a unique molecular structure which is easy to chemically modify, and has good biocompatibility. The chitosan material has the advantages of easily available raw materials and low cost, is a natural polymer material which is environment-friendly and breaks away from petroleum resources, and has been intensively studied in the fields of heavy metal adsorption, food additives, spinning, agriculture and the like in the years. However, few reports on the aspects of fluorescence sensing are provided for chitosan and derivatives thereof, so that the development of novel chitosan-based fluorescence functional materials has very important significance, and has wide application prospects in the aspects of biological imaging, sensing detection and the like.
Mercury is a heavy metal element widely used in modern industrial products and plays a great role in the fields of cosmetics, medicines, measuring instruments and the like. However, mercury ions (Hg) 2+ ) Meanwhile, the heavy metal ion with high toxicity is also a heavy metal ion, and mercury ion can be combined with sulfhydryl and disulfide groups in cell membranes or enzyme proteins, is not easy to separate, and can influence a plurality of metabolism in cells, such as synthesis of proteins and nucleic acids, so that the functions of the cells are influenced. Hg of Hg 2+ Can directly enter human body through skin, alimentary canal or respiratory tract, or finally enter human body through enrichment in food chain, thereby poisoning central nervous system, kidney, liver, oral cavity, skin, etc. At present, hg 2+ The detection method of (2) mainly comprises an electrochemical method, a capillary electrophoresis method, an atomic absorption spectrometry method and the like. However, these methods also have problems of expensive instruments, long analysis period, complex pretreatment, and the like, and are difficult to meet the requirements of detection in terms of convenience, rapidness, sensitivity, and the like. Fluorescent probe method operationSimple, high in sensitivity and low in detection limit, so that the Hg can be detected 2+ Has very important significance.
Disclosure of Invention
Aiming at the defects existing in the prior art, the technical problem to be solved by the invention is to provide a 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide compound which can meet the detection of Hg 2+ Is used in the application of the product. The invention aims to provide a preparation method of a 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe. The invention also solves the technical problem of providing 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide for detecting Hg 2+ Use of fluorescent probes.
In order to solve the technical problems, the invention adopts the following technical scheme:
2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe, which has the structural formula:
the preparation method of the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe comprises the following steps: dispersing N-chitosan-4-hydrazino-1, 8-naphthalimide in ethanol, adding isothiocyanate-1-naphthalimide, and carrying out nucleophilic addition reaction to obtain 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide.
The preparation method of the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe comprises the following specific steps:
1) Adding 0.4-0.6 g of N-chitosan-4-hydrazino-1, 8-naphthalimide, 15-30 mL of ethanol and 0.04-0.06 g of 1-naphthalene isothiocyanate into a 50mL single-neck flask with a stirrer, a thermometer and a reflux condenser, and reacting for 16-32 h at room temperature;
2) After the reaction is finished, the reaction solution is filtered by a sand core funnel, a filter cake is washed by distilled water and ethanol and then is dried in vacuum for 8-14 h at 45 ℃ to obtain the product 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide.
The prepared 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide solution (DMSO/water=9/1, v/v) does not emit fluorescence under 365nm ultraviolet irradiation, and Hg is added 2+ After that, the fluorescent color of the solution changed from colorless to bright yellow. Therefore, 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide can be used for detecting Hg 2+ Is provided.
The invention takes N-chitosan-4-hydrazino-1, 8-naphthalimide as a raw material and carries out nucleophilic addition reaction with 1-naphthalate isothiocyanate to obtain the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe. Experiments prove that the prepared solution (DMSO/water=9/1, v/v) of the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe does not emit fluorescence under 365nm ultraviolet irradiation, and Hg is added dropwise 2+ After that, the fluorescent color of the solution changed from colorless to bright yellow. Therefore, 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide can be used for detecting Hg 2+ With fluorescent probes.
The beneficial effects are that: compared with the prior art, the invention has the following advantages:
the chitosan is an alkaline polysaccharide existing in the nature, is rich in source, safe and nontoxic, and has good biocompatibility and biocompatibility. Is widely applied to the fields of food additives, textiles, agriculture, environmental protection, beauty and health care, cosmetics and the like. According to the invention, the isothiocyanate-1-naphthyl ester is grafted onto the N-chitosan-based-4-hydrazino-1, 8-naphthalimide molecular chain, so that the molecular chain not only has the excellent performance of chitosan macromolecules, but also overcomes a plurality of limitations of small molecular fluorescent compounds. The prepared 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe has the characteristics of good luminous performance, stable structure and the like. 2- (N-chitosan-1) is used for preparing the medicine,the 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide solution (DMSO/water=9/1, v/v) is added with Hg under 365nm ultraviolet irradiation without fluorescence 2+ After that, the fluorescent color of the solution is gradually changed from colorless to bright yellow, and the solution can be used for Hg 2+ Has good practical value in detection.
Drawings
FIG. 1 is an infrared spectrum of (a) N-chitosan-4-hydrazino-1, 8-naphthalimide and (b) 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide;
FIG. 2 is a high resolution spectral plot of the C1s peak of (a) N-chitosan-4-hydrazino-1, 8-naphthalimide and of (b) 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide;
FIG. 3 is a 100. Mu.M Hg solution of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide (DMSO/water=9/1, v/v) under 365nm UV irradiation 2+ Front and rear fluorescent photographs;
FIG. 4 is a solution of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide (DMSO/water=9/1, v/v) with Hg in a concentration range of 0 to 100. Mu.M 2+ A fluorescence spectrum of the effect;
FIG. 5 is a graph of fluorescence spectra of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide solution (DMSO/water=9/1, v/v) with addition of different metal ions;
FIG. 6 is a solution of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide (DMSO/water=9/1, v/v) with the addition of 100. Mu.M Hg 2+ A subsequent response time plot.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
Example 1
The synthesis reaction formula of the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe is as follows:
to a 50mL single-necked flask equipped with a stirrer, a thermometer and a reflux condenser were added 0.5-g N-chitosan-4-hydrazino-1, 8-naphthalimide, 20mL ethanol and 0.05g 1-naphthalene isothiocyanate, and reacted at room temperature for 24 hours; after the reaction is finished, the reaction solution is filtered by a sand core funnel, a filter cake is washed by distilled water and ethanol and then is dried in vacuum for 12 hours at 45 ℃ to obtain the product 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide.
The structure of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide was analyzed by FT-IR. FIG. 1 is an infrared spectrum of (a) N-chitosan-4-hydrazino-1, 8-naphthalimide and (b) 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide, respectively. Compared with N-chitosan-4-hydrazino-1, 8-naphthalimide, 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide is 1460cm -1 The characteristic peak ascribed to-N-c=s appears, indicating the introduction of 1-naphthalenyl isothiocyanate, indicating the successful preparation of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide.
XPS was used to analyze the structure of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide. FIG. 2 is a high resolution spectrum of the C1s peak of (a) N-chitosan-4-hydrazino-1, 8-naphthalimide and (b) 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide, respectively. For N-chitosan-4-hydrazino-1, 8-naphthalimide, three peaks at 287.80eV,286.0eV and 284.90eV are assigned to O-C-O respectively, C-O-C/C-O-H to and C-C/C-N peaks. In comparison with N-chitosan-4-hydrazino-1, 8-naphthalimide, 2- (N-chitosan-1, 8-naphthalimide 4-yl) -N- (naphthalen-1-yl) thiosemicarbazide exhibited a peak at 287.0eV attributed to the c=s bond, indicating the introduction of the 1-naphthalenyl isothiocyanate, indicating successful preparation of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide.
Example 2
The 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe prepared in example 1 was dispersed in a solution (DMSO/water=9/1, v/v) to prepare a concentration of 8×10 -4 g/mL of probe solution. As shown in FIG. 3, the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide solution is added into Hg without fluorescence under 365nm ultraviolet irradiation 2+ After (100. Mu.M), the fluorescent color of the solution changed from colorless to bright yellow. Therefore, 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide can be used for detecting Hg 2+ Is provided.
Example 3
The 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe prepared in example 1 was dispersed in a solution (DMSO/water=9/1, v/v) to prepare a concentration of 8×10 -4 g/mL of probe solution, and different concentrations of Hg were added as measured by a fluorescence spectrophotometer (excitation wavelength: 365nm, slit width: 10.0nm/5.0 nm) 2+ The fluorescence emission spectrum after (0 to 100. Mu.M) is shown in FIG. 4. The results show that with Hg 2+ The increasing concentration and increasing fluorescence signal intensity of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide at 543nm indicate that the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide can sensitively detect Hg in a solution 2+ Concentration of Hg 2+ As low as 7.3X10 detection limit -8 mol/L。
Example 4
The 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe prepared in example 1 was dispersed in a solution (DMSO/water=9/1, v/v) to prepare a concentration of 8×10 -4 g/mL probe solutions, 1.Hg was added separately 2+ 、2.Mg 2+ 、3.Fe 2+ 、4.Sn 2+ 、5.Ca 2+ 、6.Zn 2+ 、7.Co 2+ 、8.Na + 、9.Cd 2+ 、10.Cr 3+ 、11.Mn 2+ 、12.La + 、13.K + 、14.Al 3+ 、15.Cu 2+ 、16.Ba 2+ Fluorescence emission spectra were measured with a fluorescence spectrophotometer (excitation wavelength: 365nm, slit width: 10.0nm/5.0 nm). As can be seen from FIG. 5, hg was added 2+ The fluorescence intensity of the post-probe solution increases sharply, while other metal ions, such as Mg, are added 2+ 、Fe 2+ 、Sn 2+ 、Ca 2+ 、Zn 2+ 、Co 2+ 、Na + 、Cd 2+ 、Cr 3+ 、Mn 2+ 、La + 、K + 、Al 3+ 、Cu 2+ 、Ba 2+ Etc., the fluorescence intensity of the probe solution was hardly changed, indicating that the probe was directed to Hg 2+ Has good selectivity to Hg 2+ And (5) performing specificity detection.
Example 5
The 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe prepared in example 1 was dispersed in a solution (DMSO/water=9/1, v/v) to prepare a concentration of 8×10 -4 g/mL of probe solution, measured by a fluorescence spectrophotometer (excitation wavelength: 365nm, slit width: 10.0nm/5.0 nm) at the time of Hg addition 2+ (100. Mu.M) fluorescence emission spectrum. As can be seen from FIG. 6, hg was added 2+ The fluorescence intensity of the post-probe solution gradually increased, reached equilibrium in 5 minutes, and the fluorescence intensity remained stable for the subsequent 20 minutes. Indicating the probe pair Hg 2+ Has rapid response to Hg 2 + And (5) performing real-time detection.
Claims (6)
1.2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe, characterized by the structural formula:
2. a process for the preparation of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide according to claim 1, characterized in that: dispersing N-chitosan-4-hydrazino-1, 8-naphthalimide in ethanol, adding isothiocyanate-1-naphthalimide, and carrying out nucleophilic addition reaction to obtain 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide.
3. The method for preparing the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide fluorescent probe according to claim 2, which is characterized by comprising the following specific steps:
1) Adding 0.4-0.6 g N-chitosan-4-hydrazino-1, 8-naphthalimide, 15-30 mL ethanol and 0.04-0.06 g 1-naphthalene isothiocyanate into a 50mL single-neck flask with a stirrer, a thermometer and a reflux condenser, and reacting for 16-32 h at room temperature;
2) After the reaction is finished, the reaction solution is filtered by a sand core funnel, a filter cake is washed by distilled water and ethanol and then is dried in vacuum for 8-14 h at 45 ℃ to obtain the product 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalene-1-yl) thiosemicarbazide.
4. The method for detecting Hg by using 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide as fluorescent probe according to claim 1 2+ Is used in the field of applications.
5. The method according to claim 4, wherein the fluorescent probe solution of 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide is not fluorescent under 365nm ultraviolet light irradiation, and Hg is added 2+ After that, the fluorescent color of the solution changed from colorless to bright yellow.
6. The use according to claim 5, wherein the solvent of the 2- (N-chitosan-1, 8-naphthalimide-4-yl) -N- (naphthalen-1-yl) thiosemicarbazide fluorescent probe solution is DMSO/water in a volume ratio of 9/1.
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