CN107247029B - Ultraviolet-visible absorption spectrum analysis method for rapidly detecting composition of organic semiconductor bromination reaction product - Google Patents
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Abstract
The invention discloses an ultraviolet-visible absorption spectrum analysis method for rapidly detecting the composition of an organic semiconductor bromination reaction product. The method comprises the following steps: firstly, mixing two brominated products of an organic semiconductor according to different proportions, dissolving the brominated products in an organic solvent, and testing the ultraviolet-visible absorption spectrum of the organic solvent; respectively calculating data such as integral area, peak width, peak height obtained by subtracting the absorption curve of the mixed solution from the raw material absorption curve according to the absorption curve shapes of the mixed solutions with different composition ratios, and respectively linking the data with the composition ratios to obtain a plurality of calculation formulas, and verifying an optimal formula through experiments; and (3) testing the absorption curve of the organic semiconductor bromination reaction stock solution with unknown product composition ratio, and calculating the product composition ratio through the formulas. The method is quick to operate and low in cost, and provides a new technology for quickly detecting the composition proportion of the bromination reaction product for the field of industrial production of organic semiconductors.
Description
Technical Field
The invention relates to a new method for rapidly detecting the composition of a bromination reaction product of an organic semiconductor.
Background
Organic semiconductors, i.e., organic materials having conductivity between metal and insulator and semiconducting properties, mainly include some small organic molecules and polymers containing conjugated structures. Compared with inorganic semiconductors, organic semiconductors have the advantages of various and easy-to-deform molecular structures, good film forming property, simple preparation process, low cost, good environmental stability, capability of being manufactured into large-area flexible devices and the like. Therefore, it has wide applications in the fields of solar cells, field effect transistors, and electroluminescence.
In designing and synthesizing novel organic semiconductor materials, in order to improve the semiconductor performance, a common approach is to introduce some functional groups on the aromatic ring of the organic semiconductor materials for molecular modification, and the bromination product of the organic semiconductor molecules is an indispensable precursor in the reaction of introducing the functional groups. In the bromination reaction, a plurality of bromination products such as monobromide, dibromide, tribromo, tetrabromo and the like often appear, and it is difficult to control the reaction conditions so that only one product is produced. Therefore, in the industrial production of organic semiconductors, an analysis method for rapidly detecting the composition of the product needs to be adopted to monitor the actual reaction condition, so as to take appropriate treatment measures in time.
At present, the commonly used detection methods are mainly gas/liquid chromatography and nuclear magnetic resonance. However, instruments and equipment of the methods are expensive, the detection speed is slow, and the requirements of simple and convenient industrial analysis are difficult to meet. The ultraviolet-visible absorption spectrum method has the advantages of cheap instruments and equipment, simple sample pretreatment, high detection speed and the like, and meets the requirements of simplicity and convenience. However, the common ultraviolet-visible absorption spectrum analysis method requires that the characteristic absorption peaks of different substances appear at different wavelength positions, and the characteristic absorption peaks of the organic semiconductor bromination reaction product all appear at the same wavelength position, which does not meet the premise. Therefore, the ultraviolet-visible absorption spectrum analysis method for rapidly detecting the composition of the bromination reaction product of the organic semiconductor is provided, and has important significance for industrial production of the organic semiconductor.
Disclosure of Invention
The invention aims to provide an ultraviolet-visible absorption spectrum analysis method for rapidly detecting the composition of a bromination reaction product of an organic semiconductor.
The rapid detection and analysis method provided by the invention comprises the following steps: testing the ultraviolet-visible absorption spectrum curve of the organic semiconductor bromination reaction product mixed solution, substituting the data such as the integral area of the characteristic peak of the curve, the peak width, the peak height obtained by subtracting the raw material absorption curve and the like into a relational expression between the data and the composition proportion thereof, and calculating the composition proportion value.
The organic semiconductor material applicable to the rapid detection and analysis method provided by the invention comprises but is not limited to perylene imides (PDIs), Naphthalimides (NDIs), phthalocyanines (Pc), pyrrolopyrrole-Dione (DPP) and the like, and the structural formula of the organic semiconductor material is shown as the following formula, wherein R can represent any group:
the integral area, the peak width and the peak height of the characteristic peak of the mixed solution curve provided by the invention, and the data such as the peak height obtained by subtracting the raw material absorption curve from the integral area, the peak width and the peak height of the characteristic peak of the mixed solution curve, and the composition proportion of the characteristic peak are obtained according to the following method:
(1) firstly, any two bromination products of the organic semiconductor are mixed according to a molar ratio of 1:0 to 0:1, mixing the raw materials in different proportions, dissolving the mixture in an organic solvent which is easy to dissolve the raw materials, and respectively testing the ultraviolet-visible absorption spectrum curve of the mixed solution.
(2) And respectively calculating the integral area, the peak width and the peak height of the characteristic peak of the absorption spectrum curve of the mixed solution, and data such as the peak height obtained by subtracting the absorption curve of the mixed solution from the absorption curve of the raw material, and respectively linking the data with the composition proportion to obtain a plurality of calculation formulas.
(3) Verifying the obtained data and composition proportional relation, and screening an optimal calculation formula: carrying out bromination reaction of the organic semiconductor, after terminating the reaction, taking reaction stock solution for dilution, testing an ultraviolet-visible absorption spectrum curve of the reaction stock solution, and calculating the composition proportion of a brominated product in the reaction stock solution according to the curve by using the plurality of formulas; and (3) separating and purifying the brominated products by a chromatographic column, respectively weighing and calculating the actual composition proportion, comparing formula calculation results, and screening out a calculation formula which best meets the actual result. Finally, a calculation formula for rapidly detecting the composition of the organic semiconductor bromination reaction product is obtained.
In the method, the mole ratio of the two bromination products in the step (1) is at least 3 different ratios, the ratio number is not limited, and the numerical value is 1:0 to 0:1 are evenly distributed.
The organic solvent which is easy to dissolve the two in the step (1) comprises common organic solvents such as dichloromethane, trichloromethane, nitrogen-nitrogen dimethylformamide, tetrahydrofuran and the like.
When the raw material absorption curve in the step (2) has a plurality of characteristic peaks, subtracting the raw material absorption curve from the absorption curve of the mixed solution to obtain peak height data with the same group number, and obtaining a calculation formula with the same number.
The bromination reaction of the organic semiconductor in step (3) is a reaction that can be controlled to produce only two brominated products.
The concentrations of the mixed solution, the raw material solution and the diluted reaction solution for testing the absorption spectrum curve in the steps (1), (2) and (3) are the same and 103-106mol/L。
The invention has the following beneficial effects: the invention provides an ultraviolet-visible absorption spectrum analysis method for rapidly detecting the composition of an organic semiconductor bromination reaction product; the method can be used for the condition that the characteristic absorption peaks of the product appear at the same wavelength position; meanwhile, the method has the advantages of simple and quick operation and low cost; in industrial production, the method can detect the reaction process in real time, so that people can take appropriate measures in time to improve the production efficiency and save the cost.
Drawings
FIG. 1 shows UV-VIS absorption spectra (normalized curve) of monobromo-dibromoperylene bisimides mixed in different proportions
FIG. 2 is an enlarged view of a shaded portion of FIG. 1
FIG. 3 is a graph of the absorption curve of a monobromo-dibromoperylene bisimide mixed solution minus the absorption curve of pure PDI
FIG. 4 is a schematic diagram of area truncation in the integral area algorithm
FIG. 5 is a schematic diagram of clipping the peak width in the peak width algorithm
FIG. 6 is a schematic diagram of the peak height in the peak height algorithm
FIG. 7 is a graph of the point A of the PDI absorption curve subtracted
FIG. 8 is a graph showing the point B of the PDI absorption curve subtracted
FIG. 9 shows the UV-visible absorption spectrum (normalized curve) of the reaction solution in which the PDI as the starting material is completely reacted
FIG. 10 is a graph obtained by subtracting a pure PDI absorption curve from a reaction solution absorption curve of complete reaction of a raw material PDI
FIG. 11 shows the UV-visible absorption spectrum (normalized curve) of the reaction solution in which the reaction of the raw material PDI was incomplete
FIG. 12 is a graph of the pure PDI absorption curve subtracted from the absorption curve of the reaction starting solution in which the reaction of the raw material PDI is incomplete
Detailed Description
The following examples illustrate the present invention but are not intended to limit the scope thereof. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1: ultraviolet visible absorption spectrum test of monobromo and dibromo perylene imide mixed solution
Firstly, respectively weighing 0.00469g of monobromoperyleneimide and 0.00548g of dibromoperylene imide which are pure and are put into two erlenmeyer flasks, dissolving the monobromoperyleneimide and the dibromoperylene imide by using 100ml of dichloromethane, after a sample is fully dissolved, respectively taking 10ml of the monobromoperyleneimide and 0.00548g of dibromoperylene imide by using a measuring cylinder, putting the sample into the other two erlenmeyer flasks, diluting the sample to 100ml by using dichloromethane, and respectively obtaining the concentration of 10-5And (3) mol/L of monobromo and dibromo perylene imide solution. Then, pure monobromide and dibromo perylene imide are mixed according to the proportion of 1:0, 3:1, 2:1, 1:1, 1:2, 1:3 and 0:1, and the ultraviolet-visible absorption spectrum of the mixed solution is respectively tested. The ultraviolet-visible absorption spectrum (normalized curve) of the monobrominated perylene bisimide and the dibromoperylene bisimide mixed in different proportions is shown in figure 1, and figure 2 is a map of the shaded part in figure 1 after partial amplification.
In order to eliminate the influence of residual trace PDI in the reaction stock solution, the measured data of the ultraviolet visible absorption spectrum is normalized, the data of the ultraviolet visible absorption spectrum measured by the pure PDI solution after normalization is subtracted, then a curve is drawn, and the rule between the curve and the proportion of two brominated products in the solution is summarized. Calculated, the plotted curve is shown in FIG. 3:
example 2: method for summarizing relational expression of integral area, peak width and peak height of characteristic peak of absorption curve of mixed solution, data of peak height obtained by subtracting absorption curve of raw material from data of composition proportion of characteristic peak
By comparing the relationship between the curves of fig. 2 and 3 and the composition ratio, the relationship between the data of 5 curves and the composition ratio is obtained:
(1) integral area relation
In the above fig. 2, the difference of the integral areas of the absorption peaks at 475nm to 550nm of the ultraviolet-visible absorption spectra of the mixed solutions is compared, and the relationship between the size of the integral area and the solution ratio is summarized.
As shown in fig. 4, the lowest point at 450nm to 475nm, point a in the figure, is taken, the right hand average is shifted to point B in the figure, the truncated absorption peak is taken, and the integrated area of the shaded portion is calculated.
The area size intercepted by the ultraviolet-visible absorption spectrum of each mixed solution was calculated, and the results are shown in table 1:
TABLE 1 area data
As can be seen from the numbers in the table, as the ratio of dibromo PDI in the solution increases, the area of the ultraviolet-visible absorption spectrum also increases. And fitting the data by taking the proportion of the mixed solution as an abscissa and the area as an ordinate to obtain a linear equation: and y is 41.15571+0.56736x, namely the integral area relation.
(2) Peak width relation
In the above fig. 2, the difference of the peak width at 475nm to 550nm of the ultraviolet-visible absorption spectrum of each mixed solution is compared, and the relationship between the size of the peak width and the solute ratio in the solution is summarized.
As shown in FIG. 5, the lowest point at about 500nm, indicated as point A in the figure, was selected and translated to the left and right, intersecting point B and point C, respectively, to calculate the length of BC, and the relationship between the values and the ratio of the solution components was summarized, and the results are shown in Table 2
TABLE 2 Length of Peak Width BC in the UV-VIS absorption Spectrum of each of the mixed solutions
As can be seen from the numbers in the table, the length of BC monotonically decreases as the ratio of dibromo PDI in the solution increases. And fitting the data by taking the proportion of the mixed solution as an abscissa and the length of BC as an ordinate to obtain a linear equation: and y is 60.35714-0.144861x, namely the relation of peak width.
(3) Relation of peak height
In the above FIG. 2, the difference of the peak heights of the absorption peaks at 425nm to 500nm of the ultraviolet-visible absorption spectrum of each mixed solution is compared, and the relationship between the peak heights and the solution ratios is summarized.
As shown in FIG. 6, the sum of the heights at A, B and C (A being the lowest point, B being the highest point and C being the lowest point) is compared with the ratio of the two solutes in the solution to summarize the relationship between them. The results obtained are shown in table 3:
TABLE 3A, B, C sum of ordinates
As can be seen from the numbers in the table, as the ratio of the dibromoPDI in the solution increases, the sum of the heights at the point A, B, C gradually increases. We fit these data to a linear equation with the mixed solution ratio as abscissa and the sum of the ordinates of the A, B, C points as ordinate: and y is 1.25652+0.016x, which is the relation of peak height.
(4) Relation of A point peak height after subtracting PDI
In FIG. 3, the absorption curves of the mixed solutions minus the absorption curve of the pure PDI solution are compared, and the difference in peak height at 480nm is analyzed to summarize the relationship between the peak height and the solution ratio.
As shown in FIG. 7, the relationship between the ordinate of the point A and the solution ratio was summarized by taking the ordinate of the highest point A at about 500 nm. The results obtained are shown in Table 4
TABLE 4A-point values of different solution curves
As can be seen from the data in the table, as the ratio of the dibromo perylene imide increases, the value of the point a gradually increases, and the data is fitted to obtain a linear equation by taking the ratio of the mixed solution as the abscissa and the value of the point a as the ordinate: and y is-0.01112 +0.00955x, namely the relation of the peak height of the point A after the PDI is subtracted.
(5) Relation of B point peak height after subtracting PDI
In FIG. 3, the absorption curves of the mixed solutions minus the absorption curve of the pure PDI solution are compared, and the difference of the peak heights at 530nm in the spectrogram is analyzed to summarize the relationship between the peak heights and the solution ratios.
As shown in fig. 8: the highest point B value at about 500nm is taken, and the relation between the B point value and the solution ratio is summarized. The results obtained are shown in table 5:
TABLE 5B-point values of different solution curves
As can be seen from the data in the table, as the ratio of the dibromo perylene imide increases, the B-point value gradually increases, and the data is fitted to obtain a linear equation by taking the ratio of the mixed solution as an abscissa and the B-point value as an ordinate: and y is 0.12087+0.01714x, namely the relation of the peak height of the point B after the PDI is subtracted.
Example 3: verifying the relation, and screening the optimal calculation formula
In this example, firstly, two PDI bromination reactions were performed, and the reaction temperature was controlled to allow the reaction to generate only monobrominated PDI and dibromopdi, except that: the PDI is completely reacted once, and is not completely reacted another time; then respectively testing the ultraviolet visible absorption spectrum of the reaction stock solution, substituting the data after curve normalization into the five relational expressions, and calculating the corresponding monobrominated PDI and dibromoPDI composition proportion; purifying pure monobrominated and dibromo PDI solids obtained by two bromination reactions by a chromatographic column, and weighing to calculate the molar ratio of the monobrominated and dibromo PDI solids; and finally, comparing and verifying results obtained by calculation of the five relational expressions, screening out an optimal calculation formula, and finally obtaining the ultraviolet visible absorption spectrum analysis method for rapidly detecting the composition of the organic semiconductor bromination reaction product.
(1) Bromination reaction for only generating monobromo, dibrominated perylene imide
The bromination reaction formula is shown above, and the operation is specifically as follows:
a200 ml three-necked flask was charged with perylene imide (1.5g, 2.44mmol), potassium carbonate (1.5g, 10.9mmol) and 60ml of purified chloroform, 5ml (97.6mmol) of liquid bromine was slowly added dropwise, and the mixture was heated to 60 ℃ and stirred under reflux for two days. The progress of the bromination reaction was monitored periodically by TLC plates during the time. And (3) when the bromination reaction is finished, preparing 200ml of saturated sodium thiosulfate solution, slowly adding the saturated sodium thiosulfate solution into the reaction stock solution, stirring for 30min, and removing residual liquid bromine. And then extracting and separating liquid, taking the lower layer of red liquid, adding anhydrous sodium sulfate, fully stirring, removing water, then filtering, mixing the filtrate with a proper amount of silica gel powder, performing rotary evaporation by using a rotary evaporator, and evaporating chloroform and dichloromethane to dryness. And then, purifying the monobrominated and dibromoperylene imide by a chromatographic column by using dichloromethane/petroleum ether (the volume ratio is continuously adjusted according to the polarity condition of the product) as an eluent.
(2) Experimental verification of complete reaction of raw material PDI
In the above (1), the degree of progress of the reaction was monitored by a TCL spot plate, and the time required for completion of the reaction of the raw material PDI was 3 days. And after the bromination reaction is finished, carrying out post-treatment by the same method, drying the filtrate, then evaporating chloroform and dichloromethane to dryness, then washing by using a sodium hydroxide solution to remove sulfur, then filtering, washing by using hydrochloric acid to neutralize sodium hydroxide, then washing the sample by using distilled water to remove sodium chloride, and then drying. And finally, dissolving and diluting a small amount of desulfurized samples by using dichloromethane, measuring the ultraviolet visible absorption spectrum, separating and purifying the rest parts by using a chromatographic column to obtain monobromo and dibromo perylene bisimide solids, and weighing to calculate the proportion of the monobromo and dibromo perylene bisimide solids.
The reaction of the raw material PDI is complete, and the mass of the bromo-product after chromatographic column purification is shown in Table 6:
TABLE 6 bromo product ratio after purification of chromatographic column with complete reaction of raw material PDI
The ultraviolet-visible absorption spectrum of the reaction stock solution after the complete reaction of the raw material PDI is shown in FIG. 9:
the graph of the pure PDI absorption curve subtracted from the reaction stock absorption curve for complete reaction of the raw material PDI is shown in fig. 10:
the integrated area, peak width, peak height of point a after subtracting PDI, and peak height of point B after subtracting PDI, i.e. y value in the algorithm relation in the above 5, are analyzed from fig. 9 and 10, respectively, and substituted into the linear equation to calculate the corresponding x value. Then converted into the ratio of monobromo to dibromo perylene imide. The results are calculated as shown in table 7:
table 7 calculation results of five algorithms for complete reaction of raw material PDI
The data in the table show that the calculated ratios of monobromide and dibromo perylene imide by the five algorithms are close to the calculated ratio (1:12) by actually using chromatographic column purification, so that the algorithms are feasible under the condition of complete reaction of raw materials within an error allowable range, and the peak height relational expression and the B point peak height relational expression after subtracting PDI are preferred.
(3) Experimental verification that the reaction of the raw material PDI is incomplete
In the step (1), the TCL point plate is used for monitoring the reaction progress, and the reaction is stopped when monobrominated and dibromoperylene imide products are obviously generated and the raw materials are not reacted for within 1 to 3 days. The post-treatment is as described above (2)
The mass of the bromo product after column purification with incomplete reaction of the raw material PDI is shown in table 7:
TABLE 7 ratio of bromo-product after column purification of incomplete reaction of raw material PDI
The ultraviolet-visible absorption spectrum of the reaction solution in which the reaction of the raw material PDI was incomplete is shown in FIG. 11.
The pure PDI absorption curve was subtracted from the reaction solution absorption curve in which the reaction of the raw material PDI was incomplete, and the obtained curve is shown in FIG. 12.
The integrated area, peak width, peak height of point a after subtracting PDI, and peak height of point B after subtracting PDI, i.e. y values in the above 5 algorithm relations, are analyzed from fig. 11 and 12, respectively, and substituted into the linear equation to obtain the corresponding x values. Then converted to the ratio of monobromo to dibromoperylene imide, the results are shown in table 8:
TABLE 8 calculation results of five algorithms for incomplete reaction of raw material PDI
As can be seen from the data in the table, the results of the five algorithms are close to those calculated for the actual purification separation when the starting material is not fully reacted (1: 10). These algorithms are feasible in the case of incomplete reaction of the starting materials, preferably the integral area relation, the PDI-subtracted a-point peak height relation and the PDI-subtracted a-point peak height relation.
Claims (6)
1. An ultraviolet-visible absorption spectrum analysis method for rapidly detecting the composition of organic semiconductor bromination reaction products is characterized in that:
firstly, mixing two brominated products of an organic semiconductor according to different proportions, dissolving the brominated products in an organic solvent, and testing the ultraviolet-visible absorption spectrum of the organic solvent;
respectively calculating the integral area, the peak width and the peak height of the mixed solution according to the absorption curve shapes of the mixed solutions with different composition ratios, and obtaining first peak height data and second peak height data after subtracting the first peak and the second peak of the absorption curve of the mixed solution from the raw material absorption curve, and respectively linking the data with the composition ratios to obtain a plurality of calculation formulas, and verifying an optimal formula through experiments;
testing the absorption curve of the organic semiconductor bromination reaction stock solution with unknown product composition ratio, and collecting the data, namely calculating the product composition ratio through the formulas;
the organic semiconductor bromination reaction is a reaction which can control the conditions and only generate two bromination products; the mixed solution is prepared by mixing two bromination products according to a molar ratio of 1:0 to 0:1 mixing at different ratios, dissolving in organic solvent with high solubility, and making into powder with concentration of 103-106mol/L。
2. The uv-vis absorption spectroscopy for the rapid detection of the composition of brominated reaction products of organic semiconductors according to claim 1, wherein: the calculation formula of the integral area data and the proportion of the absorption curve of the bromide mixed solution is as follows: and fitting the composition proportion of the mixed solution as an abscissa and the integral area of the solution absorption curve as an ordinate to obtain an equation.
3. The UV-VIS absorption spectrometry for rapid detection of the brominated reaction products of an organic semiconductor according to claim 1, wherein the formula for the calculation of the peak width data and the ratio of the absorption curve of the bromide mixed solution is: and taking the composition proportion of the mixed solution as an abscissa, taking the lowest peak valley point between characteristic peaks in an absorption curve of the mixed solution as a standard, measuring the total peak width of all the characteristic peaks as an ordinate, and fitting to obtain an equation.
4. The UV-VIS absorption spectrometry for rapid detection of the brominated reaction products of an organic semiconductor according to claim 1, wherein the formula for the calculation of the peak height data and the ratio of the absorption curve of the bromide mixture solution is: and fitting the composition proportion of the mixed solution as an abscissa and the sum of the heights of the beginning, the end and the highest point of a certain characteristic peak of the absorption curve as an ordinate to obtain an equation.
5. The UV-VIS absorption spectrometry for rapidly detecting the composition of a brominated reaction product of an organic semiconductor of claim 1, wherein the formula for calculating the ratio of the peak height obtained by subtracting the absorption curve of the brominated reaction product mixed solution from the absorption curve of the raw material to the composition ratio is as follows: and fitting an equation obtained by taking the composition proportion of the mixed solution as an abscissa and taking the height of a certain peak of a curve obtained by subtracting the absorption curve of the mixed solution from the absorption curve of the raw material as an ordinate.
6. Use of the assay of claim 1 to detect the compositional ratio of brominated products of an organic semiconductor.
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