CN109679119B - Synthesis and application of main-object supramolecular hydrogel based on quaternized water-soluble column [5] arene - Google Patents
Synthesis and application of main-object supramolecular hydrogel based on quaternized water-soluble column [5] arene Download PDFInfo
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Abstract
The invention discloses a main-guest supramolecular hydrogel based on quaternized water-soluble column [5] arene, which is a supramolecular hydrogel with white aggregation-induced fluorescence emission performance, and is formed by self-assembling quaternized water-soluble column [5] arene and a benzimidazole iodonium salt compound in BN pure water. The supramolecular hydrogel has stimulus responsiveness to paraquat: the addition of paraquat can change the fluorescence of the supramolecular hydrogel from white to yellow, and the gel state of the hydrogel SH-DP is destroyed. Organic solvents of ethanol, petroleum ether, DMF, acetone and adiponitrile are respectively added into the supermolecular hydrogel SH-DP, only the addition of the adiponitrile can quench the fluorescence of the supermolecular hydrogel SH-DP, and the gel state of the hydrogel SH-DP is destroyed, so that the recognition performance has certain application value in the field of molecular recognition.
Description
Technical Field
The invention relates to preparation of a supermolecule host-guest hydrogel, in particular to preparation of a host-guest supermolecule hydrogel based on quaternized water-soluble column [5] arene; the invention also relates to the stimulation responsiveness, the molecular recognition performance and the application of the supramolecular host-guest hydrogel.
Background
Paraquat, a fast herbicide, has a contact action and a certain systemic action. Can be rapidly absorbed by green tissues of plants to make the plants wither. Paraquat is an extremely toxic pesticide of grade I, abuse of which results in high persistence in the environment, and, due to its high water solubility, it may be a potential contaminant of agricultural, drinking and groundwater. In addition, strong epidemiological evidence suggests that paraquat exposure is associated with the development of parkinson's disease. The organic molecule paraquat has great toxicity to human bodies, no specific antidote is used, and the death rate of oral poisoning can reach over 90 percent, so that the paraquat is also important for identifying and detecting the paraquat.
The pillar arene is a columnar structure formed by connecting hydroquinone through bridging methylene, and becomes a new macrocyclic host molecule due to unique symmetrical structures, such as a rigid columnar structure and an electron-rich cavity, relatively easy modification and excellent molecular recognition capability. These intrinsic properties determine the column [5] arene as an excellent host molecule, which can complex with different cations (e.g. benzimidazole) and neutral guests. Therefore, the research on molecular recognition achieved by the supramolecular organic hydrogel which forms a host-guest complex through the self-assembly of the host-guest of the macrocyclic molecular column arene is receiving wide attention.
Disclosure of Invention
The invention aims to provide a preparation method of host-guest supramolecular hydrogel based on quaternized water-soluble column [5] arene;
the invention also aims to provide the host-guest supramolecular hydrogel based on the quaternized water-soluble column [5] arene with super stimulus responsiveness, molecular recognition performance and specific application.
Supermolecule hydrogel of host and guest based on quaternized water-soluble column [5] arene
The supramolecular hydrogel with white aggregation-induced fluorescence emission performance is formed by self-assembling quaternized water-soluble column [5] arene and benzimidazole iodonium salt compounds in pure water according to the molar ratio of 1: 0.25-1: 1.5. The specific synthesis method comprises the following steps: adding benzimidazole iodonium salt (BN) and quaternized column [5] arene (DP 5) into pure water (the content of a host and an object in the pure water is 0.026-0.158 g/ml) in a molar amount of 1: 0.25-1: 1.5, heating to dissolve, and cooling to room temperature to obtain the stable supramolecular hydrogel SH-DP of the host and the object.
The structural formula of the bulk quaternized water soluble column [5] arene DP5 is as follows:
wherein 1 to 7 represent different hydrogen protons on the water-soluble column [5] arene DP 5.
The structural formula of the guest benzimidazole iodonium salt compound BN is as follows:
wherein a-e respectively represent different hydrogen protons on the benzimidazole iodonium salt compound BN;
the structural formula of the obtained supermolecule hydrogel SH-DP is as follows:
wherein 1 to 7 represent different hydrogen protons in the water-soluble pillared [5] arene DP5
FIG. 1 is a nuclear magnetic hydrogen spectrum diagram of benzimidazole iodonium salt BN. The chemical shift values of BN, as determined by hydrogen spectroscopy, were Δ 7.76-7.65 (multiplet, 4H), 5.49 (singlet, 2H), 4.11 (singlet, 3H), 3.81 (singlet, 3H), 1.71-1.67 (triplet,J=12 Hz, 2H), 1.45-1.42 (triplet,J =12 Hz, 2H), 1.21 (singlet, 6H), 0.85-0.82 (triplet,J = 12 Hz，3H）。
FIG. 2 is a partial nuclear magnetic diagram of SH-DP (BN with DP 5). Wherein (a) BN: DP5=1: 1; (b) BN; (c) DP 5. Can be found in H in graph (a)a-He The (BN) proton peaks all shifted to low field and H1 (DP 5) to high field, indicating that the long alkyl groups of BN penetrated into the bulk DP5 cavity. Thereby obtaining the supermolecule host-guest hydrogel SH-DP.
FIG. 3 shows SH-DP (BN and DP5)The two-dimensional nuclear magnetic spectrum of (1). Wherein A/B represents Hg、Hf(BN), H2 (DP 5) proton peaks have correlation, C/D represents HdThe (BN), H1 (DP 5) proton peak was correlated, which further illustrates the penetration of the long alkyl chain portion of the guest molecule BN into the bulk column arene (DP 5) cavity.
Fluorescent responsiveness of bi-and supermolecule host-guest hydrogel SH-DP
1. Fluorescence property of supermolecule host-guest hydrogel SH-DP
The BN guest molecule alone does not gel in pure water, and can form stable supermolecular host-guest hydrogel SH-DP after DP5 is added. The supermolecule host-guest hydrogel SH-DP has good aggregation-induced fluorescence emission performance. When the excitation wavelength is 280nm, the supermolecular hydrogel SH-DP emits white fluorescence.
Stimulus response performance of three-molecule host-guest hydrogel SH-DP
1. Stimulation response performance of supermolecular hydrogel SH-DP to Paraquat (PQ)
The experimental process comprises the following steps: 4.0 mg of the gelator BN and 10.5 mg of the body DP5 (BN: DP5=1: 0.5) were weighed out, placed in a vial, 0.2ml of pure water was added, heated under a closed condition to be completely dissolved, and after standing and cooling to room temperature, the solution in the vial was observed to form a uniform and stable gel. 0.5 equivalent of paraquat (0.5 equivalent relative to the bulk DP5) was then added and after a period of standing the state of the gel SH-DP was found to be destroyed, i.e. the gel collapsed to a yellow sol (see FIG. 4).
The experimental results are as follows: the addition of paraquat to the supramolecular hydrogel SH-DP of the host and the guest can change the fluorescence of the supramolecular hydrogel SH-DP from white to yellow, and the gel state of the hydrogel SH-DP is destroyed. The supramolecular hydrogel SH-DP has stimulus responsiveness to paraquat, and the property enables the supramolecular hydrogel SH-DP to be used for simply detecting a large amount of paraquat in pesticides.
2. Stimulation response of supramolecular hydrogel SH-DP to Adiponitrile (ABN)
The experimental process comprises the following steps: 4.0 mg of the gelator BN and 10.5 mg (0.5 times equivalent to BN) of DP5 were weighed into a small gel bottle, 0.2ml of pure water was added thereto, and heated under a closed condition to be completely dissolved, and after standing and cooling to room temperature, the solution in the small gel bottle was observed to form a uniform and stable gel. 0.5 equivalent of adiponitrile (0.5 equivalent relative to bulk DP5) was then added and after standing for a period of more than ten minutes the collapse of gel SH-DP, i.e.the gel state, was broken to become a sol, was found (see FIG. 5).
The experimental results are as follows: the fluorescence of the supramolecular hydrogel SH-DP can be weakened by adding adiponitrile in the supramolecular hydrogel SH-DP of the host and the guest, and the gel state of the hydrogel SH-DP is destroyed. The supramolecular hydrogel SH-DP is shown to have a stimulus-responsiveness to adiponitrile, a property that makes it useful for differentiating adiponitrile from simple organic solvents according to changes in the gel state.
FIG. 6 is a scanning electron micrograph of BN, SH-DP, SH-DP-ADN, SH-DP-PQ. Scanning electron microscope experiments show that the microscopic morphology of the guest molecule BN is in an amorphous state. After the host and the object are assembled into the supermolecular water-gelled SH-DP, the microstructure of the supermolecular water-gelled SH-DP is in a small sheet stacking structure. And the appearance changes after competitive object molecules of Adiponitrile (ADN)/Paraquat (PQ) are added, namely a regular lamellar structure and a small blocky structure, so that the stimulus responsiveness of Adiponitrile (ADN)/Paraquat (PQ) to supermolecular water-gelling SH-DP is further proved.
In conclusion, through the host-guest effect, the synthesized supramolecular host-guest hydrogel SH-DP can stimulate and respond to specific molecules by multiple guests, and the competitive host-guest stimulus response performance has potential development value in the aspect of stimulus response materials.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of BN.
FIG. 2 is a partial nuclear magnetic hydrogen spectrum of BN, DP5, BN/DP 5.
FIG. 3 is a two-dimensional nuclear magnetic spectrum of BN/DP 5.
FIG. 4 is a test of the stimulus responsiveness of the supramolecular host-guest hydrogel SH-DP to Paraquat (PQ)
FIG. 5 is a test of the stimulus responsiveness of the supramolecular host-guest hydrogel SH-DP to Adiponitrile (ADN).
FIG. 6 is a scanning electron micrograph of BN, SH-DP, SH-DP-ABD, SH-DP-PQ.
Detailed Description
The preparation and application of the supramolecular host-guest hydrogel of the invention are further illustrated by the following specific examples.
EXAMPLE I preparation of supramolecular host-guest hydrogels
1. Synthesis of iodonium salt of benzimidazole BN: 1.03 g (3.0 mmol) of 2-undecyl-1-H-benzimidazole-3-acetic acid methyl ester, 1.27 g (9.0 mmol) iodomethane, dissolved in 50mL acetonitrile, reacted at 85-90 ℃ for 30 h; after the reaction, the reaction mixture was cooled to room temperature, the solvent was removed by suction filtration, and the mixture was recrystallized from acetone/water to precipitate 1.3747g of a white crystalline solid, the yield was 95%, and the melting point: 108-110 ℃;
2. synthesis of host DP 5: see literature: { the Qi Lin of the cell culture system,*a Lu Liu,a Feng Zheng,aPeng-Peng Mao,a Juan Liu,*b You-Ming Zhang, aHongYaoa and Tai-Bao Wei*aA water-soluble pillar[5]arene-based chemosensorfor highly selective and sensitivefluorescence detection of L-methionine. RSC Adv., 2017, 7, 34411–34414}；
3. preparation of supramolecular host-guest hydrogel (SH-DP): weighing host molecule DP 5: 0.0105g (4.1X 10)- 6mol), guest molecule BN: 0.0040g (8.2X 10)-6mol) is added into 0.2ml of pure water and heated to be completely dissolved; and then cooling to room temperature to obtain the stable supramolecular host-guest hydrogel SH-DP. When the excitation wavelength is 280BNm, the supramolecular hydrogel SH-DP emits white fluorescence.
EXAMPLE II stimulation response of supramolecular host-guest hydrogels SH-DP to Paraquat (PQ)
Adding 0.5 equivalent weight of Paraquat (PQ) into the supermolecular hydrogel SH-DP; the change in SH-DP of the hydrogel was observed over time. As a result, it was found that the fluorescence of the hydrogel SH-DP changed from white to yellow, and the gel state thereof was completely destroyed after about ten minutes.
EXAMPLE III stimulation response of supramolecular host-guest hydrogels SH-DP to Adiponitrile (ADN)
When 0.5 times equivalent of adiponitrile is added into the supermolecular hydrogel SH-DP, the gel state of the supermolecular hydrogel SH-DP is completely destroyed in less than ten minutes, and the white fluorescence of the gel is quenched, which indicates that the Adiponitrile (ADN) is added to have stimulus responsiveness to the hydrogel SH-DP. And the addition of other solvents can not quench the white fluorescence of the supramolecular hydrogel SH-DP.
Claims (6)
1. A supermolecular hydrogel of host and guest based on quaternized water-soluble column [5] arene is characterized in that: is a supermolecular hydrogel with white aggregation-induced fluorescence emission performance, which is formed by self-assembling quaternized water-soluble column [5] arene and benzimidazole iodonium salt compound BN in pure water;
the structural formula of the bulk quaternized water soluble column [5] arene DP5 is as follows:
wherein 1 to 7 respectively represent different hydrogen protons on the water-soluble column [5] arene DP 5;
the structure of the guest benzimidazole iodonium salt compound BN is as follows:
wherein a-e respectively represent different hydrogen protons on the benzimidazole iodonium salt compound BN;
the structural formula of the obtained supermolecule hydrogel SH-DP is as follows:
wherein 1 to 7 represent different hydrogen protons on the water-soluble column [5] arene DP 5.
2. The method for synthesizing supramolecular hydrogel based on host-guest of quaternized water-soluble column [5] arene according to claim 1, wherein: adding benzimidazole iodonium salt BN and quaternized column [5] arene DP5 into pure water according to the molar weight of 1: 0.25-1: 1.5, heating to dissolve, and cooling to room temperature to obtain the stable host-guest supramolecular hydrogel SH-DP.
3. The method for synthesizing supramolecular hydrogel based on host-guest of quaternized water-soluble column [5] arene according to claim 2, wherein: the content of the host and the object in the pure water is 0.026-0.158 g/ml.
4. The supramolecular hydrogel of a subject-guest based on quaternized water-soluble column [5] arene of claim 1, wherein: it has a stimulus-responsiveness to paraquat: the addition of paraquat to the supramolecular hydrogel SH-DP of the host and the guest can change the fluorescence of the supramolecular hydrogel SH-DP from white to yellow, and the gel state of the hydrogel SH-DP is destroyed.
5. Use of the supramolecular hydrogel based on quaternized water-soluble pillared [5] arene host-guest molecules according to claim 4 for the identification of adiponitrile.
6. Use of the supramolecular hydrogel based on a quaternized water-soluble pillared [5] arene host-guest according to claim 5 for the identification of adiponitrile: organic solvents of ethanol, petroleum ether, DMF, acetone and adiponitrile are respectively added into the supermolecular hydrogel SH-DP, only the addition of the adiponitrile can quench the fluorescence of the supermolecular hydrogel SH-DP, and the gel state of the hydrogel SH-DP is destroyed.
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| CN110055057B (en) * | 2019-05-16 | 2021-03-23 | 西北师范大学 | Column [5] arene-based supramolecular polymer gel, and synthesis and application thereof |
| CN110105947B (en) * | 2019-05-16 | 2021-03-23 | 西北师范大学 | Synthesis and application of quaternization column [5] arene and 2' 2-biphenyl benzimidazole inclusion complex |
| CN110590648B (en) * | 2019-09-27 | 2022-05-03 | 西北师范大学 | Synthesis of tripodia column [5] arene, detection and application of tripodia column [5] arene in adsorbing methyl viologen |
| CN110724280B (en) * | 2019-10-18 | 2022-05-24 | 西北师范大学 | Preparation and application of supramolecular polymer hydrogel with thermal response and metal gel thereof |
| CN111393370B (en) * | 2020-03-30 | 2022-07-19 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN113173919B (en) * | 2021-05-20 | 2022-07-12 | 西北师范大学 | Preparation and application of amphiphilic bis-benzimidazole derivative and supramolecular sensor thereof |
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