CN112083044B - Multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound and preparation method and application thereof - Google Patents
Multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a method for manufacturing a volatile organic gas sensor based on a multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound. 4-cyanophenylboronic acid, 1,3, 5-tribromobenzene and dicyandiamide are used as raw materials, and a monomer C of the multiple hydrogen bond organic supramolecular nanorod is synthesized by an organic synthesis method33H27N15(ii) a Adopting a solvent induced precipitation method to obtain a target multiple hydrogen bond organic supramolecular nanorod; then compounding with graphene oxide by an ultrasonic and magnetic stirring method to obtain a multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound; and (3) dropping the aqueous solution of the compound on the gold cross electrode, wherein only the electrodes at two ends are exposed on the surface of the gold cross electrode, and the rest parts are covered by the compound, so that the sensor capable of detecting the volatile organic gas is prepared.
Description
Technical Field
The invention relates to a multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound as well as a preparation method and application thereof, belonging to the technical field of functional nano-material preparation.
Technical Field
The multiple hydrogen bond organic supermolecule nano material is a supermolecule nano material self-assembled by multiple hydrogen bond interaction between organic monomers. The material not only has the characteristics of nano material size effect, surface effect and the like, but also has the characteristics of various organic supermolecular composition structures, easy regeneration and the like. Recently, scientists have synthesized a variety of multiple hydrogen bonding organic supramolecular nanomaterials. The stable multiple hydrogen bond organic supermolecule nano material has shown excellent performance in the fields of substance separation, biological medicine and the like.
The volatile organic compounds are chemical reagents widely applied in industrial production, and the excessive volatile organic compounds in the air pollute the atmospheric environment and harm the human health. Therefore, the content of volatile organic gases in the atmosphere is strictly monitored. Meanwhile, a small amount of volatile organic gases exist in the exhaled breath of the human body, and the gases are biomarkers of certain diseases, so that the health condition of the human body can be judged according to the concentration of the gases in the exhaled breath of the human body. The development of a high-sensitivity and high-selectivity volatile organic gas sensor has important significance for environmental management and protection, early diagnosis of human diseases and the like.
Disclosure of Invention
In order to solve the technical problems, the invention provides a multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite material and a preparation method and application thereof.
The technical scheme provided for solving one of the technical problems is as follows: a preparation method of a multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound is characterized by comprising the following steps: the method comprises the following steps:
(1) under the heating condition, the synthesized multiple hydrogen bond organic supermolecule nanorod monomer C33H27N15Dissolving in dimethyl sulfoxide;
(2) slowly dripping the filtrate into acetone by adopting a solvent induced precipitation method to finally separate out the target multiple hydrogen bond organic supramolecular nanorod;
(3) and (3) dispersing the nanorods obtained in the step (2) in water, adding graphene oxide, performing ultrasonic treatment, and stirring to obtain the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound.
Preferably, the multiple hydrogen bond organic supramolecular nanorod monomer C in the step (1)33H27N15The preparation method of the compound is to use 4-cyanophenylboronic acid, 1,3, 5-tribromobenzene and dicyandiamide as raw materials and synthesize the compound by an organic synthesis method.
Preferably, the heating temperature in the step (1) is 100-180 ℃, and the multiple hydrogen bond organic supramolecular nanorod monomer C33H27N15And dimethylThe molar ratio of the radical sulfoxide is 1: 350-400.
Preferably, the dropping speed in the step (2) is 1-2 ml per minute, and the volume ratio of the acetone to the dimethyl sulfoxide solution is 100: 1-2.
Preferably, the mass ratio of the water to the nanorods in the step (3) is 4: 1-3, the mass ratio of the nanorods to the graphene oxide is 5: 1-3, the ultrasonic time is 1-3 hours, and the stirring time is 6-24 hours.
Preferably, the heating temperature in the step (1) is 150 ℃, and the multiple hydrogen bond organic supramolecular nanorod monomer C33H27N15The molar ratio of the dimethyl sulfoxide to the dimethyl sulfoxide is 1: 384; the dropping speed in the step (2) is 1.5 ml per minute, and the volume ratio of the acetone to the dimethyl sulfoxide solution is 200: 3; the mass ratio of the water to the nanorods in the step (3) is 2:1, the mass ratio of the nanorods to the graphene oxide is 5:2, the ultrasonic time is 2 hours, and the stirring time is 12 hours.
The technical scheme provided for solving one of the technical problems is as follows: a preparation method of a multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound is prepared according to the preparation method.
The technical scheme provided for solving one of the technical problems is as follows: the application of the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound can be applied to gas sensing, separation and storage.
Preferably, the water dispersion of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound is dripped on the surface of the gold cross electrode and dried in the natural air, and the prepared electrode can be used for testing volatile organic gas at normal temperature.
The technical scheme provided for solving one of the technical problems is as follows: the multiple hydrogen bond organic supermolecule nanorod in the preparation method of the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound can be applied to the fields of gas sensing, substance separation, storage and bionic materials.
The invention has the beneficial effects that:
the multiple hydrogen bond organic supermolecule nanorod can provide a large specific surface area, and meanwhile, a plurality of organic functional groups are arranged in the material, and the two points are beneficial to the interaction between the multiple hydrogen bond organic supermolecule nanorod and gas molecules, so that the multiple hydrogen bond organic supermolecule nanorod can be used for preparing a gas sensor. Through compounding with the graphene oxide, the conductivity of the sensor is improved, the specific surface area of the sensor is increased, and the detection limit of the sensor is reduced.
1. The preparation of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound improves the conductivity, the specific surface area and the film forming property of a sensing material.
2. The multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound gas sensor can detect volatile organic compound gas at room temperature.
3. The multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound gas sensor disclosed by the invention has the advantages of low detection limit on acetone gas, high response speed and high selectivity, and can be self-recovered.
Drawings
FIG. 1 shows multiple hydrogen bonding organic supramolecular nanorod monomer C in example 133H27N15The synthetic route of (1).
FIG. 2 shows multiple hydrogen bonds of organic supramolecular nanorod monomer C in example 133H27N15H of (A) to (B)1NMR chart.
FIG. 3 shows multiple hydrogen bonds of organic supramolecular nanorod monomer C in example 133H27N15C of (A)12NMR chart.
FIG. 4 is a TEM image of the multiple hydrogen bonding organic supramolecular nanorods in example 2.
Fig. 5 is a TEM image of the multiple hydrogen bonding organic supramolecular nanorod/graphene oxide complex in example 5.
Fig. 6 is the nitrogen adsorption-desorption isotherms of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite and the multiple hydrogen bond organic supramolecular nanorods in example 5.
FIG. 7 is a comparison graph of the film-forming properties of the multiple hydrogen bond organic supramolecular nanorods, graphene oxide, and multiple hydrogen bond organic supramolecular nanorods/graphene oxide composites in example 5.
Fig. 8 is a graph of the resistance change of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide complex in example 10 under different concentrations of acetone gas.
FIG. 9 is a radar chart of the response value, response time, recovery time, and recovery curve fitting equation coefficients a and b of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite in example 10 under different volatile organic gases of 20 ppm.
Detailed Description
For a better understanding of the present invention, the technical solutions of the present invention will be described in detail below by way of specific embodiments with reference to the accompanying drawings.
Example 1: method for preparing multiple hydrogen bond organic supermolecule nano rod monomer
(1) Under nitrogen protection, 2.1g of 4-cyanophenylboronic acid, 1g of 1,3, 5-tribromobenzene, 0.74g of tetrakis (triphenylphosphine) palladium, and 4.04g of Na2CO3Dissolving in 60 ml of N, N-dimethylformamide and 20 ml of water, refluxing at 100 ℃ for 72 hours, cooling the reaction to room temperature, distilling under reduced pressure to remove the organic solvent, extracting the residue with dichloromethane (100 ml. times.3), washing with saturated brine (50 ml. times.2), spin-drying, and purifying by column chromatography to obtain the product 1.
(2)0.45g of the product 1, 0.37g of dicyandiamide, 0.06g of 85% potassium hydroxide are dissolved in 30 ml of ethylene glycol monomethyl ether, the mixture is refluxed for 48 hours at 125 ℃, the reaction is cooled to room temperature, the solid is filtered out, and the solid is washed by hot water and ethanol respectively and dried in vacuum, so that the multiple hydrogen bond organic supramolecular nanorod monomer is obtained.
The product of example 1 was analyzed for multiple hydrogen bond organic supramolecular nanorod monomer, as shown in FIG. 2, H of multiple hydrogen bond organic supramolecular nanorod monomer1NMR chart, as shown in FIG. 3, C of multiple hydrogen bond organic supramolecular nanorod monomer12NMR chart by H1NMR chart and C12The NMR chart can show that the obtained multiple hydrogen bond organic supermolecule nanorod monomer is consistent with the product structure in the figure 1.
Example 2: preparation method of multiple hydrogen bond organic supermolecule nano-rod
(1)150 take a photographTaking 700mg of multiple hydrogen bond organic supermolecule nanorod monomer C at the temperature of the Deg33H27N15Dissolved in 30 ml of dimethyl sulfoxide and insoluble matter was filtered off.
(2) And (3) dropwise adding the solution into 200 ml of acetone at a speed of 1.5 ml per minute by adopting a solvent induced precipitation method to prepare the multiple hydrogen bond organic supramolecular nanorod.
The multiple hydrogen bond organic supramolecular nanorods of the product obtained in example 2 are analyzed, as shown in fig. 4, a TEM image of the multiple hydrogen bond organic supramolecular nanorods can show that the multiple hydrogen bond organic supramolecular nanorods finally form a nanorod structure through the TEM image.
Example 3: preparation method of multiple hydrogen bond organic supermolecule nano-rod
(1) Taking 700mg of multiple hydrogen bond organic supramolecular nanorod monomer C at 100 DEG C33H27N15Dissolved in 27 ml of dimethyl sulfoxide and insoluble matter was filtered off.
(2) And (2) dropwise adding the solution into 200 ml of acetone at a speed of 1 ml per minute by adopting a solvent induced precipitation method to prepare the multiple hydrogen bond organic supramolecular nanorod.
The product multiple hydrogen bond organic supramolecular nanorods in example 2 can also be obtained by using example 3.
Example 4: preparation method of multiple hydrogen bond organic supermolecule nano-rod
(1) Taking 700mg of multiple hydrogen bond organic supermolecule nanorod monomer C at 180 DEG C33H27N15Dissolved in 32 ml of dimethyl sulfoxide, and insoluble matter was filtered off.
(2) And 4 ml of the solution is dripped into 200 ml of acetone at the speed of 2 ml per minute by adopting a solvent induced precipitation method to prepare the multiple hydrogen bond organic supramolecular nanorod.
The product multiple hydrogen bond organic supramolecular nanorods in example 2 can also be obtained by using example 4.
Example 5: method for preparing volatile organic compound gas sensor by using multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound
(1) And dispersing 5 mg of multiple hydrogen bond organic supramolecular nanorods in 10 ml of water, adding 2 mg of graphene oxide, carrying out ultrasonic treatment for 2 hours, then stirring for 12 hours, and centrifuging to obtain the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound.
(2) And (3) dripping the aqueous solution of the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound on the gold cross electrode, naturally drying to form a film, only exposing the electrodes at two ends on the surface of the gold cross electrode, and covering the rest parts with the compound to obtain the gas sensor capable of measuring the concentration of the volatile organic gas.
The product of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite obtained in example 3 is analyzed, as shown in fig. 5, a TEM image of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite is shown, and the surface of the final multiple hydrogen bond organic supramolecular nanorod composite graphene oxide can be illustrated through the TEM image. As shown in fig. 6, the nitrogen adsorption-desorption isotherm of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite can show that the specific surface area of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite is higher than that of the multiple hydrogen bond organic supramolecular nanorod by the isotherm. As shown in fig. 7, a comparison graph of the film forming properties of the multiple hydrogen bond organic supramolecular nanorods, the graphene oxide and the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite shows that the film forming properties of the multiple hydrogen bond organic supramolecular nanorods/graphene oxide composite are significantly improved.
Example 6: method for preparing volatile organic compound gas sensor by using multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound
(1) And dispersing 2.5 mg of multiple hydrogen bond organic supermolecule nanorods in 10 ml of water, adding 2 mg of graphene oxide, carrying out ultrasonic treatment for 1 hour, then stirring for 6 hours, and centrifuging to obtain the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound.
The multiple hydrogen bonding organic supramolecular nanorod/graphene oxide complex of example 5 can also be prepared using example 6.
Example 7: method for preparing volatile organic compound gas sensor by using multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound
(1) And (3) dispersing 7.5 mg of multiple hydrogen bond organic supramolecular nanorods in 10 ml of water, adding 2 mg of graphene oxide, carrying out ultrasonic treatment for 3 hours, then stirring for 24 hours, and centrifuging to obtain the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound.
The multiple hydrogen bonding organic supramolecular nanorod/graphene oxide complex of example 5 can also be prepared using example 7.
Example 8: method for preparing volatile organic compound gas sensor by using multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound
(1) And (3) dispersing 5 mg of multiple hydrogen bond organic supermolecule nanorods in 10 ml of water, adding 1 mg of graphene oxide, carrying out ultrasonic treatment for 1.5 hours, then stirring for 8 hours, and centrifuging to obtain the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound.
The multiple hydrogen bonding organic supramolecular nanorod/graphene oxide complex of example 5 can also be prepared using example 8.
Example 9: method for preparing volatile organic compound gas sensor by using multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound
(1) And (3) dispersing 5 mg of multiple hydrogen bond organic supramolecular nanorods in 10 ml of water, adding 3 mg of graphene oxide, carrying out ultrasonic treatment for 2.5 hours, then stirring for 18 hours, and centrifuging to obtain the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound.
The multiple hydrogen bonding organic supramolecular nanorod/graphene oxide complex of example 5 can also be prepared using example 9.
Example 10: application of volatile organic gas sensor for testing concentration of organic volatile gas
(1) Electrodes at two ends of the gas sensor are connected with a data collector (Agilent 34972A) through a lead, and the sensing performance of the volatile organic compound gas is tested by the data collector at normal temperature; the gas sensor is placed in a sealed container.
(2) Is difficult to openMeasuring base line resistance R of gas sensor when volatile organic gas0。
(3) And measuring the resistance when the volatile organic gas is introduced, wherein the concentration is gradually increased from 0.2ppm to 100ppm, and the carrier gas is air.
(4) At each concentration tested, the resistance of the sensor changed with the addition of the volatile organic gas and subsequently recovered itself.
(5) The measured resistance is converted into delta R/R0Wherein R is0Is the baseline resistance in the absence of the volatile organic gas, and Δ R is the maximum value of the amount of change in resistance with respect to the baseline resistance when the volatile organic gas is passed.
(6) Will be Delta R/R0Plotting time, the resistance change increases with increasing volatile organic gas concentration.
The results of the above tests are analyzed, and as shown in fig. 8, the resistance change of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide composite is shown as a graph, wherein the resistance change becomes larger as the concentration of acetone gas increases.
As shown in fig. 9, the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound responds to 20ppm of different volatile organic gases, and the fitting equation coefficients of response values, response times, recovery times and recovery curves corresponding to the different volatile organic gases in the graph are all different, so that good selectivity is shown.
It can be seen from fig. 8 and 9 that the resistance of the sensor changes greatly with the addition of volatile organic gases of different concentrations. The multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound has different responses to different organic volatile gases, can be used for detecting different volatile organic gases, and has good selectivity.
Therefore, the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound can be used for preparing a volatile organic gas sensor.
The invention is not limited to the specific technical solutions described in the above embodiments, and all technical solutions formed by equivalent substitutions are within the scope of the invention as claimed.
Claims (10)
1. A preparation method of a multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound is characterized by comprising the following steps: the method comprises the following steps:
(1) under the heating condition, the synthesized multiple hydrogen bond organic supermolecule nanorod monomer C33H27N15Dissolving in dimethyl sulfoxide;
(2) slowly dripping the filtrate into acetone by adopting a solvent induced precipitation method to finally separate out the target multiple hydrogen bond organic supramolecular nanorod;
(3) dispersing the nanorods obtained in the step (2) in water, adding graphene oxide, performing ultrasonic treatment, and stirring to obtain a multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound;
said C is33H27N15The structural formula of (A) is as follows:
2. the method for preparing the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 1, wherein the method comprises the following steps: the multiple hydrogen bond organic supermolecule nanorod monomer C in the step (1)33H27N15The preparation method takes 4-cyanophenylboronic acid, 1,3, 5-tribromobenzene and dicyandiamide as raw materials, and the preparation method comprises the following steps:
3. the method for preparing the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 1, wherein the method comprises the following steps: the heating temperature in the step (1) is 100-180 ℃, and the multiple hydrogen bond organic supermolecule nanorod monomer C33H27N15The molar ratio of the compound to the dimethyl sulfoxide is 1: 350-400.
4. The method for preparing the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 1, wherein the method comprises the following steps: the dropping speed in the step (2) is 1-2 ml per minute, and the volume ratio of the acetone to the dimethyl sulfoxide solution is 100: 1-2.
5. The method for preparing the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 1, wherein the method comprises the following steps: the mass ratio of water to the nanorods in the step (3) is 4: 1-3, the mass ratio of the nanorods to the graphene oxide is 5: 1-3, the ultrasonic time is 1-3 hours, and the stirring time is 6-24 hours.
6. The method for preparing the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 1, wherein the method comprises the following steps: the heating temperature in the step (1) is 150 ℃, and the multiple hydrogen bond organic supramolecular nanorod monomer C33H27N15The molar ratio of the dimethyl sulfoxide to the dimethyl sulfoxide is 1: 384; the dropping speed in the step (2) is 1.5 ml per minute, and the volume ratio of the acetone to the dimethyl sulfoxide solution is 200: 3; the mass ratio of the water to the nanorods in the step (3) is 2:1, the mass ratio of the nanorods to the graphene oxide is 5:2, the ultrasonic time is 2 hours, and the stirring time is 12 hours.
7. A multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound is characterized in that: the preparation method according to any one of claims 1, 2, 3, 4, 5 and 6.
8. The use of multiple hydrogen bonding organic supramolecular nanorods/graphene oxide complexes according to claim 7, characterized in that: the compound is applied to gas sensing, separation and storage.
9. The use of multiple hydrogen bonding organic supramolecular nanorods/graphene oxide complexes according to claim 7, characterized in that: and (3) dripping the water dispersion solution of the multiple hydrogen bond organic supermolecule nanorod/graphene oxide compound on the surface of the gold cross electrode, and drying in natural air to obtain the electrode for testing the volatile organic gas at normal temperature.
10. The application of the multiple hydrogen bond organic supramolecular nanorod obtained by the preparation method of the multiple hydrogen bond organic supramolecular nanorod/graphene oxide compound according to claim 2 is characterized in that: the method is used in the fields of gas sensing, substance separation, storage and bionic materials.
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