CN111996001A - Organic framework material with fluorescence recognition function on p-nitrobenzene, preparation method and application - Google Patents
Organic framework material with fluorescence recognition function on p-nitrobenzene, preparation method and application Download PDFInfo
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Abstract
The invention discloses an organic frame material with fluorescence identification to nitrobenzene, a preparation method and application thereof, which is characterized in that zirconium-based metal-organic frame material with active carboxylic acid sites is formed by zirconium tetrachloride and organic acid, and the preparation comprises the following steps: performing ligand replacement and synthesis reaction on a mixture of zirconium tetrachloride, 1, 4-phthalic acid, 1, 3-phthalic acid and N, N-dimethylformamide at 110-130 ℃, and modifying reactants by europium nitrate to obtain a europium-modified zirconium-based metal-organic framework material; the organic framework material can be used for carrying out fluorescence recognition on nitrobenzene in natural water. Compared with the prior art, the fluorescent recognition material has the advantages of fluorescent recognition of small molecular organic matters, quick operation, high sensitivity, quick response speed and strong anti-interference capability, is a fluorescent recognition material with great development potential, and has potential application value in the field of materials science.
Description
Technical Field
The invention relates to the technical field of fluorescent identification materials, in particular to an organic framework material with fluorescent identification function on nitrobenzene, a preparation method thereof and application of the organic framework material in fluorescent identification of the nitrobenzene.
Technical Field
Fluorescence identification is a novel detection and identification technology based on fluorescent materials, and compared with the traditional detection and identification technology, the fluorescence identification has the advantages of high sensitivity, low cost, simplicity in operation and the like while completing a detection task. The fluorescence recognition can possibly replace traditional detection means such as Raman spectrum and the like, and becomes a high-efficiency, sensitive and short-time fluorescence recognition technology with great development potential. As a key material for fluorescence recognition, the property of the fluorescent material determines the efficiency of fluorescence recognition
In recent years, due to tailorability and controllability, fluorescent recognition materials of small molecular organic substances have received much attention from materials scientists. See: Y.J. Cui, Y.F. Yue, G.D. Qian, B.L. Chen, chem. Rev., 2012, 112(2): 1126-chem. Res.1162, B.Yan, Acc. chem. Res, 2017, 50(11): 2789-2798.
The reported fluorescent identification materials can be divided into two types: inorganic systems and organic systems. Inorganic systems have excellent chemical stability and are capable of working under extreme conditions, while organic systems have good tailorability and are capable of designing fluorescent materials starting from specific analytes. See: C.R. Maldonado, A. Touchavela, A.C. Jones, J.C. Marequarias, chem. Commun, C.M. Tyrakowski, P.T. Snee, anal. chem., 2014;86(5) 2380-. Because the metal-organic framework which has selective fluorescent recognition for organic micromolecule organic matters such as nitrobenzene and the like has certain difficulty in synthesis, the research on the fluorescent recognition material of the metal-organic framework is less, see: H.R. Fu, Y.ZHao, T.Xie, M.L.Han, L.F.Ma, S.Q.Zang, J.Mater. chem. C, 2018, 6, 6440, K.Vellingieria, D.W.Boukhvalovb, S.K.Pandeyc, A.Deepd, K, H, Kim, Sens. Actuators B, 2017, 245: 305-.
The metal-organic framework material is used as a novel inorganic-organic hybrid material, has the stability of an inorganic system and the modifiability of an organic system, and is an ideal material for fluorescent identification. Therefore, the research on the novel fluorescent materials is particularly important.
Disclosure of Invention
The invention aims to provide an organic framework material with fluorescence recognition on nitrobenzene, a preparation method and application thereof, aiming at the defects of the prior art, the zirconium-based metal with selective fluorescence recognition on nitrobenzene and organic acid are adopted to form the zirconium-based metal-organic framework material with active carboxylic acid sites, the organic framework material can be used as a fluorescence recognition material for small molecular organic matters after being modified by europium and is used for carrying out fluorescence recognition on nitrobenzene in natural water, the material is a fluorescence recognition material with high efficiency, sensitivity and response speed, development potential, strong anti-interference capability, good repeatability, non-contact measurement and the like, has potential application value in the field of materials science, and has been widely concerned and researched.
The purpose of the invention is realized as follows: the organic frame material with fluorescence recognition function for p-nitrobenzene is characterized in that zirconium-based metal-organic frame material with active carboxylic acid sites is formed by adopting zirconium tetrachloride and organic acid, the chemical general formula of the zirconium-organic frame material is Eu @ Zr-MOFs, and the organic acid is one or a mixture of terephthalic acid and isophthalic acid.
The preparation method of the organic framework material with fluorescence identification on the nitrobenzene is characterized in that the preparation method of the rare earth metal-organic framework material specifically comprises the following steps:
the method comprises the following steps: mixing zirconium-based metal, 1, 4-phthalic acid, 1, 3-phthalic acid and N, N-dimethylformamide in a mass ratio of 1: 0.45-0.75: 0.04-0.07: 400-500, replacing the ligand at the temperature of 110-130 ℃, and performing synthetic reaction for 20-25 hours to obtain an intermediate product of white powder;
step two: washing the obtained intermediate product with N, N-dimethylformamide and methanol in sequence, drying, soaking in a methanol solution, soaking for 48-72 hours, and performing vacuum drying to obtain a zirconium-based metal-organic framework material;
step three: dispersing the zirconium-based metal-organic framework material in a europium salt aqueous solution with the concentration of 8-15 mmol/L, stirring for 20-25 hours in the dark, washing a reaction product with methanol, and then drying in vacuum to obtain the europium-modified zirconium-based metal-organic framework material.
The preparation method of the rare earth metal-organic framework fluorescent identification material is characterized in that the europium salt is europium nitrate or europium chloride.
The methanol soak replaces methanol every 12 hours; the drying temperature is 90-110 ℃; the temperature of the vacuum drying is 50-70 ℃.
The fluorescence identification application of the organic framework material with fluorescence identification on the nitrobenzene is characterized in that europium-modified zirconium-based metal-organic framework material is dispersed in water for the fluorescence identification application of the nitrobenzene, so that the nitrobenzene in the water is rapidly detected, and the weight-volume ratio of the zirconium-based metal-organic framework material to the water is 1 g: 450-550 ml.
Compared with the prior art, the invention has the following beneficial effects:
1) the metal framework material prepared by the invention has a plurality of emission peaks at 579 nm, 590 nm, 614 nm, 651 nm and 700 nm, the luminescent property of the material is strongly dependent on the concentration of nitrobenzene in an aqueous solution, and the material can be used for fluorescence identification of nitrobenzene in the aqueous solution. Specifically, when the concentration of nitrobenzene is in the range of 0-180 mu mol/L, the intensity of an emission peak at 614 nm is reduced along with the increase of the concentration of nitrobenzene in a solution system. The rapid detection can be realized, the emission intensity of the material can reach balance within 1 minute, and the anti-interference capability is strong. The detection result is not influenced by external factors such as probe concentration, temperature and other organic matters.
2) The rare earth metal-organic framework material prepared by the invention has high fluorescence quantum yield, the absolute fluorescence quantum yield is 3.62%, the luminescent color can be seen by naked eyes, the luminescent color is changed from pink to light purple along with the increase of the concentration of nitrobenzene, real-time imaging and in-situ detection can be realized, and the rare earth metal-organic framework material is expected to be practically applied in the field of real-time nitrobenzene detection and monitoring.
3) The rare earth metal-organic framework material prepared by the invention can be used for detecting the concentration of nitrobenzene in natural water, has obvious fluorescence response and obvious fluorescence color change within the concentration range of 0-180 mu mol/L of nitrobenzene, and has higher sensitivity and identification degree compared with the previously reported fluorescence probes of the same type.
Drawings
FIG. 1 is a spectrum of a rare earth metal-organic framework material prepared in example 1;
FIG. 2 is a fluorescent photograph of the rare earth metal-organic framework material prepared in example 1 under an ultraviolet lamp;
FIG. 3 is a graph showing the emission spectra of the rare earth metal-organic framework material prepared in example 1 at different concentrations of nitrobenzene;
FIG. 4 is a fluorescent photograph of the rare earth metal-organic framework material prepared in example 1 under the conditions of 0 and 180. mu. mol/L nitrobenzene;
referring to FIG. 5, a graph of fluorescence intensity versus nitrobenzene concentration for the zirconium-based metal-organic framework material prepared in example 1 is shown;
referring to FIG. 6, a zirconium-based metal-organic framework material F/F prepared for example 10The Stern-Volmer line graph.
Detailed Description
The zirconium-based metal-organic framework material with active carboxylic acid sites is formed by zirconium tetrachloride with selective fluorescent recognition on nitrobenzene and organic acid, the chemical general formula of the zirconium-based metal-organic framework material is Eu @ Zr-MOFs, and the organic acid is one or a mixture of terephthalic acid and isophthalic acid.
The preparation and use of the invention are further illustrated by the following specific examples:
example 1
The specific synthesis of the rare earth metal-organic framework material comprises the following steps:
the method comprises the following steps: dissolving 0.163 g of zirconium tetrachloride, 0.104 g of 1, 4-phthalic acid and 0.012g of 1, 3-phthalic acid in 80 mL of N, N-dimethylformamide, carrying out magnetic stirring treatment for 20 minutes, transferring the uniformly mixed solution to a 150 mL closed reaction kettle, reacting at 120 ℃ for 10 hours, and naturally cooling to room temperature after the reaction is finished to obtain a white powder intermediate product;
step two: the above intermediate product was washed 3 times with DMF by centrifugation at 10000rmp for ten minutes each, and the centrifuged powder was dried in an oven at 100 ℃ and then dispersed in 100 mL of methanol, stirred for 36 hours, and replaced with fresh methanol every 12 hours. The dispersion was washed 3 times with methanol at 10000rmp for ten minutes each time, and dried under vacuum at 150 ℃ for 12 hours after washing to obtain 0.300 g of white powder as a zirconium-based metal-organic framework material.
Step three: dispersing the above zirconium-based metal-organic framework material in 60 mL of Eu (NO) with a concentration of 10 mmol/L3)3Stirring in the water solution for 24 hours in a dark place, washing for 3 times by using methanol, and then drying for 10 hours in vacuum at the temperature of 60 ℃ to obtain the europium-modified zirconium-based metal-organic framework material.
Referring to FIG. 1, the emission of the zirconium-based metal-organic framework material prepared in the above example under 254 nm excitation and the excitation spectrum at 614 nm have an absolute fluorescence quantum yield of 3.62%.
Referring to FIG. 2, the zirconium-based metal-organic framework material prepared in the above example was observed to have a significant fluorescence with the naked eye under a 254 nm ultraviolet lamp.
The rare earth metal-organic framework material prepared by the embodiment is detected by optical performance, and the material is fully proved to have a good fluorescence phenomenon.
Example 2
The optical properties of the europium-modified zirconium-based metal-organic framework material prepared in example 1 were measured in nitrobenzene solutions of different concentrations.
5.4 mg of the zirconium-based metal-organic framework material prepared in example 1 was weighed, dispersed in 2.7 mL of distilled water, and measured for light emitting properties. Using a microsyringe, 300. mu.L of nitrobenzene solutions (0 to 200. mu. mol/L) having different concentrations were measured in each of the above dispersions, and the change in fluorescence intensity was measured.
Referring to FIG. 3, the maximum emission wavelength of the zirconium-based metal-organic framework material prepared in example 1 was around 614 nm.
Referring to FIG. 4, the zirconium-based metal-organic framework material prepared in example 1 showed no significant fluorescence to the naked eye under a 254 nm UV lamp under 180. mu. mol/L nitrobenzene.
Referring to fig. 5, the fluorescence intensity of the zirconium-based metal-organic framework material prepared in example 1 decreased as the concentration of nitrobenzene increased.
Referring to FIG. 6, at an added nitrobenzene concentration of 180. mu. mol/L, the quenching efficiency was 89.12%, with a Stern-Volmer quenching constant of 24514.36M-1. The material can be well applied to the fluorescence identification of nitrobenzene. The Stern-Volmer equation: F/F0=1+Ksv[Q]Wherein F is0Is the fluorescence intensity of the rare earth metal-organic framework in the absence of nitrobenzene; f is the fluorescence intensity of the rare earth metal-organic framework in the presence of nitrobenzene; [ Q ]]Is nitro radicalThe benzene concentration, Ksv, is the Stern-Volmer quenching constant.
The invention indicates a new direction for preparing the multifunctional fluorescent metal-organic framework material, and the europium-modified zirconium-based metal-organic framework is used as a fluorescent identification material for small molecular organic matters, thereby having potential application value in the field of materials science. The invention is further described and not intended to be limited to the specific embodiments disclosed, but rather, the invention is to be accorded the full scope and equivalents thereof.
Claims (5)
1. The organic frame material with fluorescence recognition function for p-nitrobenzene is characterized in that zirconium-based metal-organic frame material with active carboxylic acid sites is formed by adopting zirconium tetrachloride and organic acid, the chemical general formula of the zirconium-based metal-organic frame material is Eu @ Zr-MOFs, and the organic acid is one or a mixture of terephthalic acid and isophthalic acid.
2. The preparation method of the organic framework material with fluorescence identification for p-nitrobenzene according to claim 1, characterized in that the preparation of the rare earth metal-organic framework material specifically comprises the following steps:
the method comprises the following steps: mixing zirconium-based metal, 1, 4-phthalic acid, 1, 3-phthalic acid and N, N-dimethylformamide according to a mass ratio of 1: 0.45-0.75: 0.04-0.07: 400-500, and carrying out a synthesis reaction at 110-130 ℃ for 20-25 hours to obtain a white powder intermediate product;
step two: washing the obtained intermediate product with N, N-dimethylformamide and methanol in sequence, drying, soaking in a methanol solution, soaking for 48-72 hours, and performing vacuum drying to obtain a zirconium-based metal-organic framework material;
step three: dispersing the zirconium-based metal-organic framework material in a europium salt aqueous solution with the concentration of 8-15 mmol/L, stirring for 20-25 hours in the dark, washing a reaction product with methanol, and then drying in vacuum to obtain the europium-modified zirconium-based metal-organic framework material.
3. The method for preparing an organic framework material with fluorescence recognition for nitrobenzene according to claim 2, wherein the europium salt is europium nitrate or europium chloride.
4. The method for preparing the organic framework material with fluorescence identification on p-nitrobenzene according to claim 2, wherein the methanol soaking is performed by replacing methanol every 12 hours; the drying temperature is 90-110 ℃; the temperature of the vacuum drying is 50-70 ℃.
5. The application of the organic framework material with fluorescence recognition function on p-nitrobenzene according to claim 1, wherein europium-modified zirconium-based metal-organic framework material is dispersed in water for the application of fluorescence recognition on p-nitrobenzene, so as to realize the rapid detection of nitrobenzene in the water, and the weight-volume ratio of the zirconium-based metal-organic framework material to the water is 1 g: 450-550 mL.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114044915A (en) * | 2021-11-26 | 2022-02-15 | 河南中医药大学 | Preparation method and application of ratiometric fluorescent probe Eu/Zr-UiO-66 with high selectivity on cyclohexanone |
| CN114509416A (en) * | 2022-01-21 | 2022-05-17 | 浙江大学 | Fluorescent array sensor for distinguishing nitrophenol compounds and preparation method thereof |
| CN114957700A (en) * | 2022-07-14 | 2022-08-30 | 之江实验室 | Metal organic framework material for chloride ion sensing and preparation method thereof |
| CN115197439A (en) * | 2022-08-12 | 2022-10-18 | 复旦大学 | Plant interface super-assembly SAFs fluorescent material and preparation method thereof |
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2020
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Non-Patent Citations (1)
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| 夏超: "基于镧系金属—有机框架荧光探针的功能化设计及其传感性能研究", 《中国优秀博硕士学位论文全文数据库（博士）工程科技I辑》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114044915A (en) * | 2021-11-26 | 2022-02-15 | 河南中医药大学 | Preparation method and application of ratiometric fluorescent probe Eu/Zr-UiO-66 with high selectivity on cyclohexanone |
| CN114044915B (en) * | 2021-11-26 | 2022-05-17 | 河南中医药大学 | Preparation method and application of ratiometric fluorescent probe Eu/Zr-UiO-66 with high selectivity on cyclohexanone |
| CN114509416A (en) * | 2022-01-21 | 2022-05-17 | 浙江大学 | Fluorescent array sensor for distinguishing nitrophenol compounds and preparation method thereof |
| CN114957700A (en) * | 2022-07-14 | 2022-08-30 | 之江实验室 | Metal organic framework material for chloride ion sensing and preparation method thereof |
| CN115197439A (en) * | 2022-08-12 | 2022-10-18 | 复旦大学 | Plant interface super-assembly SAFs fluorescent material and preparation method thereof |
| CN115197439B (en) * | 2022-08-12 | 2023-06-20 | 复旦大学 | Plant interface super-assembled SAFs fluorescent material and preparation method thereof |
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