CN113354639A - Perylene diimide derivative and preparation method and application thereof - Google Patents

Perylene diimide derivative and preparation method and application thereof Download PDF

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CN113354639A
CN113354639A CN202010149594.8A CN202010149594A CN113354639A CN 113354639 A CN113354639 A CN 113354639A CN 202010149594 A CN202010149594 A CN 202010149594A CN 113354639 A CN113354639 A CN 113354639A
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perylene diimide
pdi
diimide derivative
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perylene
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张浩力
宋其蔚
孙春霖
王小珍
张橙
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Lanzhou University
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Abstract

A perylene diimide derivative and a preparation method and application thereof belong to the field of photoelectric materials. A perylene diimide derivative is characterized in that a bay position of the perylene diimide derivative is introduced into an ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene aromatic conjugated system, and the perylene diimide derivative can generate singlet splitting in a film state, so that the perylene diimide derivative can be applied to preparation of photoelectric materials. The preparation method of the perylene diimide derivative comprises the steps of uniformly mixing 6, 12-dibromo-N, N-N-pentane-perylene diimide, tetratriphenylphosphine palladium, anhydrous potassium carbonate, a substituent and a solvent, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas, and reacting for 24-28 h to obtain a crude product of the perylene diimide derivative, wherein the substituent comprises 2-biphenyl boric acid, 3-biphenyl boric acid, 4-biphenyl boric acid, alpha-naphthalene boric acid or beta-naphthalene boric acid. The preparation method is simple and convenient, the yield is high, and the prepared perylene diimide derivative is stable.

Description

Perylene diimide derivative and preparation method and application thereof
Technical Field
The application relates to the field of photoelectric materials, in particular to a perylene diimide derivative and a preparation method and application thereof.
Background
Singlet fission was first observed in the anthracene crystal in 1965, to explain the extremely low fluorescence quantum yield. Then in the 70 s of the 20 th century, around 1968, Swenberg et al considered an important pathway for solid state fluorescence quenching in tetracene crystals to occur as singlet fission. Meanwhile, Yarmus et al reported for the first time electron paramagnetic resonance spectra of triplet excitons in mono-crystalline tetracenes, where the spin deflection and emission present in mono-crystalline tetracenes is derived from triplet excitons generated by singlet fission.
The external quantum efficiency of organic semiconductor solar cells based on singlet splitting currently exceeds 100%. However, the singlet split solar cell is still in the primary development stage at present, and compared with the traditional small molecule or polymer solar cell, the photoelectric conversion efficiency of the current singlet split solar cell is too low, and a long way is needed for industrial mass production. Therefore, in order to improve the photoelectric performance of the solar cell, it is important to find more systems capable of generating singlet fission and more organic small molecules or polymer systems with good photo-thermal stability.
Disclosure of Invention
The application provides a perylene diimide derivative, a preparation method and application thereof, wherein the perylene diimide derivative can generate singlet fission, so that the perylene diimide derivative can be applied to preparation of photoelectric materials.
The embodiment of the application is realized as follows:
in a first aspect, the present application provides a perylene diimide derivative having the following structural formula:
Figure BDA0002401903290000021
wherein R comprises ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene.
In the technical scheme, an ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene aromatic conjugated system is introduced into the bay position of the perylene diimide derivative, and the perylene diimide derivatives PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N can be obtained through respective synthesis.
The perylene diimide derivative can generate singlet fission, so that the perylene diimide derivative can be applied to preparation of photoelectric materials.
In combination with the first aspect, in a first possible example of the first aspect of the present application, the fluorescence quantum yield of the thin film of the perylene diimide derivative is 6 to 22%.
In a second possible example of the first aspect of the present application in combination with the first aspect, the solution of the perylene diimide derivative has a fluorescence quantum yield of 50 to 85%.
In a second aspect, the application example provides a preparation method of the perylene diimide derivative, which includes heating, refluxing and stirring the first mixture at 125-135 ℃ for 24-28 hours under the protection of an inert gas, and obtaining a crude perylene diimide derivative.
Wherein the first mixture is prepared by the following method:
uniformly mixing 6, 12-dibromo-N, N-pentane-perylene diimide, palladium tetratriphenylphosphine, anhydrous potassium carbonate, a substituent and a solvent.
The substituent includes 2-biphenylboronic acid, 3-biphenylboronic acid, 4-biphenylboronic acid, alpha-naphthylboronic acid or beta-naphthylboronic acid.
In the technical scheme, the preparation method of the perylene diimide derivative is simple and convenient, the yield is high, and the prepared perylene diimide derivative is stable.
In a first possible example of the second aspect of the present application in combination with the second aspect, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033 to 0.044mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009 to 0.0012mol/L, the molar concentration of anhydrous potassium carbonate is 0.23 to 0.30mol/L, and the molar concentration of the substituent is 0.16 to 0.22 mol/L.
In a second possible example of the second aspect of the present application in combination with the second aspect, the solvent includes anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran, or N, N-dimethylformamide.
In the above examples, water cannot be present in the entire reaction system solvent, and the solvent cannot react with the raw materials.
In combination with the second aspect, in a third possible example of the second aspect of the present application, the preparation method of the perylene diimide derivative further includes separation and purification, where the separation and purification includes sequentially extracting a crude perylene diimide derivative with dichloromethane, water, and saturated saline solution, spin-drying, and then performing column chromatography silica gel chromatography for separation and purification to obtain the perylene diimide derivative.
In the above example, the excessive palladium tetratriphenylphosphine can be extracted and removed by using dichloromethane, the excessive potassium carbonate can be extracted and removed by using water, the excessive moisture can be extracted and removed by using saturated saline solution, and after the saturated saline solution is dried by spinning, the perylene diimide derivative which is relatively pure can be obtained by separating and purifying by using column chromatography silica gel chromatography.
In a fourth possible example of the second aspect of the present application in combination with the second aspect, the above-mentioned 6, 12-dibromo-N, N-pentane-perylene diimide is prepared by:
and uniformly mixing the N, N-pentane-perylene diimide, the iodine simple substance, the liquid bromine and the dichloromethane to obtain a second mixture, and reacting the second mixture at 35-45 ℃ for 48-52 hours.
In the above examples, the preparation method of the 6, 12-dibromo-N, N-pentane-perylene diimide is simple and high in yield, and the prepared 6, 12-dibromo-N, N-pentane-perylene diimide is stable.
In a fifth possible example of the second aspect of the present application in combination with the second aspect, the above-mentioned N, N-pentane-perylene diimide is prepared by:
uniformly mixing 3,4,9, 10-perylene tetracarboxylic anhydride, 3-aminopentane and imidazole, and reacting at 135-150 ℃ for 3-5 h under the protection of inert gas.
In the above example, the preparation method of the N, N-pentane-perylene diimide is simple and convenient, the yield is high, and the prepared N, N-pentane-perylene diimide is stable.
In a third aspect, the present application provides a perylene diimide derivative for use in the preparation of an optoelectronic material.
In the technical scheme, the perylene diimide derivative can generate singlet fission to generate a higher triplet energy level (1.10-1.28eV), so that the perylene diimide derivative can be applied to preparation of photoelectric materials.
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In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are required to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present application and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained from the drawings without inventive effort.
FIG. 1 shows UV absorption/fluorescence emission spectra of films of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N of the present application;
FIG. 2 is a graph showing transient absorption spectra of films of the present application PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N;
FIG. 3 is a kinetic profile of films of the present applications PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N, and PDI-C5-2N;
FIG. 4 is a three-dimensional spectrum of transient absorption of the present application PDI-C5-2 in toluene solution;
FIG. 5 is a graph showing transient absorption spectra of PDI-C5-2 of the present application in toluene solution;
FIG. 6 is a graph of the kinetics of the present application PDI-C5-2 in toluene solution;
FIG. 7 is a three-dimensional spectrum of transient absorption of the present application PDI-C5-1N in toluene solution;
FIG. 8 is a graph showing transient absorption spectra of PDI-C5-1N of the present application in toluene solution;
FIG. 9 is a graph of the kinetics of the present application PDI-C5-1N in toluene solution;
FIG. 10 is a three-dimensional spectrum of transient absorption of the present application PDI-C5-2N in toluene solution;
FIG. 11 is a graph showing transient absorption spectra of PDI-C5-2N of the present application in toluene solution;
FIG. 12 is a graph of the kinetics of the present application PDI-C5-2N in toluene solution;
FIG. 13 is a three-dimensional spectrum of transient absorption of the present application PDI-C5-3 in toluene solution;
FIG. 14 is a graph showing transient absorption spectra of PDI-C5-3 of the present application in toluene solution;
FIG. 15 is a graph of the kinetics of the present application PDI-C5-3 in toluene solution;
FIG. 16 is a three-dimensional spectrum of transient absorption of the present application PDI-C5-4 in toluene solution;
FIG. 17 is a graph showing transient absorption spectra of PDI-C5-4 of the present application in toluene solution;
FIG. 18 is a graph of the kinetics of the present application PDI-C5-4 in toluene solution.
Detailed Description
Embodiments of the present application will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present application and should not be construed as limiting the scope of the present application. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The perylene diimide molecules have the characteristics of larger skeleton of a rigid conjugated pi system, nearly 100% of luminous quantum yield, high photo-thermal stability, strong electron-withdrawing capability, higher electron mobility, strong and wide absorption of a visible region and the like.
The inventor finds that the perylene diimide can change the energy level of the front line molecular orbit and the torsion angle of the molecule by modifying, thereby influencing the accumulation of the molecule. And the introduction of a conjugated group at the bay position can also expand the pi conjugated skeleton of the whole molecule, thereby influencing the coupling effect among perylene diimide molecules, meeting the basic energy requirement of singlet fission and generating a higher triplet energy level (1.10-1.28 eV).
The following detailed description is directed to a perylene diimide derivative, a preparation method and an application thereof in the embodiments of the present application:
the embodiment of the application provides a perylene diimide derivative, which has the following structural formula:
Figure BDA0002401903290000061
wherein R comprises ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene.
The perylene diimide derivatives PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N can be synthesized respectively by introducing ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene aromatic conjugated systems into the bay position of the perylene diimide.
The structural formula of the PDI-C5-2 compound is as follows:
Figure BDA0002401903290000071
the structural formula of the PDI-C5-3 compound is as follows:
Figure BDA0002401903290000072
the structural formula of the PDI-C5-4 compound is as follows:
Figure BDA0002401903290000081
the structural formula of the PDI-C5-1N compound is as follows:
Figure BDA0002401903290000082
the structural formula of the PDI-C5-2N compound is as follows:
Figure BDA0002401903290000091
the fluorescence quantum yield of the thin film of the perylene diimide derivative is 6-22%.
Wherein, the fluorescence quantum yield of the film of PDI-C5-2 is 6.51%, the fluorescence quantum yield of the film of PDI-C5-3 is 21.34%, the fluorescence quantum yield of the film of PDI-C5-4 is 24.1%, the fluorescence quantum yield of the film of PDI-C5-1N is 6.1%, and the fluorescence quantum yield of the film of PDI-C5-2N is 13.95%.
The fluorescence quantum yield of the solution of the perylene diimide derivative is 50-85%.
Wherein, the fluorescence quantum yield of the solution of PDI-C5-2 is 84.02%, the fluorescence quantum yield of the solution of PDI-C5-3 is 75.21%, the fluorescence quantum yield of the solution of PDI-C5-4 is 82.54%, the fluorescence quantum yield of the solution of PDI-C5-1N is 55.32%, and the fluorescence quantum yield of the solution of PDI-C5-2N is 50.26%.
The inventors found that the fluorescence quantum yield of the perylene diimide derivatives in the thin film state is very small compared to the solution state, and that PDI-C5-2 and PDI-C5-1N are even an order of magnitude smaller, indicating that in solution, the singlet excitons of the perylene diimide are essentially in the form of fluorescence, i.e., in the form of radiative decay, to the ground state. While the singlet excitons in the thin film are not all attenuated to the ground state by the radiation attenuation, there are other ways to compete with the radiation attenuation, and it is presumed that there is a possibility that singlet fission occurs in the thin film, and the singlet excitons are split into triplet excitons by the singlet fission.
Firstly, respectively dissolving PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N in chloroform saturated solution at normal temperature, dripping the chloroform saturated solution dissolved with PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N or PDI-C5-2N on a cover glass, and volatilizing and drying the solvent under a natural open system to respectively prepare PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N films.
The film PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N are respectively subjected to femtosecond transient absorption test, the excitation light is 400 nanometers, and the detection light test area is a visible area from 400 nanometers to 800 nanometers. The measured data are processed by Surface Xplorer software, and a transient three-dimensional spectrogram, a relative absorption spectrogram changing along with time and a dynamic fitting spectrogram are obtained by Origin arrangement and mapping.
FIG. 1 is a graph showing ultraviolet absorption/fluorescence emission spectra of thin films of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N, in which the solid line portion is ultraviolet absorption and the dotted line portion is fluorescence emission, FIG. 2 is a graph showing transient absorption spectra of thin films of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N, and FIG. 3 is a graph showing kinetics of thin films of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N.
According to transient absorption spectrograms of PDI-C5-2, PDI-C5-3 and PDI-C5-4, except that signals at 555nm, 570nm and 575nm which are matched with an ultraviolet visible absorption spectrogram are ground state bleaching signals, a new signal is generated in the spectrogram and is respectively overlapped with the ground state bleaching signals at 545nm, 550nm and 520nm, but the new signal can be seen as a positive signal, and the intensity of the signal is not reduced along with the increase of time. A weak positive absorption signal between 600nm and 800nm wide as molecule S1-SnThe signal of excited state reabsorption. The PDI-C5-1N has a ground state bleaching signal at 540nm, a new long-life peak at 525nm along with time, the peak is overlapped with the ground state bleaching signal and does not decay along with the increase of time, and a weak positive absorption signal with the width of 570nm to 800nm is S1-SnThe excited state reabsorbs the signal. The PDI-C5-2N has a ground state bleaching signal at 500nm, a new long-life peak at 480nm, a superposition with the ground state bleaching signal and no attenuation with the increase of time, and a wide and weak positive absorption signal S at 540nm to 800nm1-SnThe excited state reabsorbs the signal. In a longitudinal view of transient absorption spectrograms of five perylene diimide molecules at different times, the inventor finds that biphenyl groups are introduced at the positions of perylene diimide bay so that basic state bleaching signals of the molecules are more red-shifted, and naphthalene groups are introduced so that singlet excitons generated by the basic state bleaching have higher energy. Multiple small peaks in a ground state bleaching region of a PDI-C5-1N transient absorption spectrum are similar to signals obtained by ultraviolet absorption. The PDI-C5-2N molecule has a downward peak at 600nmOverlapping the S1-Sn excited state reabsorption signal appears as a positive signal, and the downward peak should be the stimulated emission signal by comparison with the emission spectrum of the molecule. According to the transient absorption spectrogram of the perylene diimide published in the prior literature, the signal intensity of the ground state bleaching is increased and then reduced along with the increase of time, and the signal is red-shifted along with the increase of time, so that the singlet splitting process is generated. The new long-life signal which is not degraded and is superposed with the ground state bleaching is presumed to be a perylene diimide triplet signal, the signal contained in a spectrogram is subjected to component decomposition and life fitting analysis through singular value decomposition and global fitting, a sensitizer PdPc (OBu)8 is excited at the wavelength of 740nm to generate singlet excitons, triplet excitons are generated through intersystem crossing, the triplet excitons of the sensitizer are observed through transient absorption spectroscopy, and the process of transmitting energy to the triplet excitons of the perylene diimide derivative is further observed, so that the fact that the singlet fission process does occur in the states of PDI-C5-2, PDI-C5-3 and PDI-C5-1N in a thin film state is deepened.
The triplet yields were calculated from the ratio of the ground state bleaching, and the triplet yields of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N in the thin film state were calculated to be 183%, 154%, 151%, 160%, 135%, respectively. The perylene diimide derivative has high yield in a thin film state. And by comparing the substituent introduced at the position of the perylene diimide bay, the introduction of the biphenyl group enables the molecules to generate singlet fission and generate more triplets. By comparison of five molecules, the triplet yields of PDI-C5-2 and PDI-C5-1N were higher, probably because their aromatic substituents were closer to the central, large conjugated backbone, so that stronger coupling facilitated the singlet splitting process.
Then, PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N were dissolved in a toluene solvent, respectively, to prepare solutions of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N.
The test of femtosecond transient absorption is respectively carried out on solutions of PDI-C5-2, PDI-C5-3, PDI-C5-4, PDI-C5-1N and PDI-C5-2N, the excitation light is 400 nanometers, and the detection light test area is a visible area from 400 nanometers to 800 nanometers. The measured data are processed by Surface Xplorer software, and a transient three-dimensional spectrogram, a relative absorption spectrogram changing along with time and a dynamic fitting spectrogram are obtained by Origin arrangement and mapping.
FIG. 4 is a three-dimensional spectrum of transient absorption of PDI-C5-2 in toluene solution, FIG. 5 is a spectrum of transient absorption of PDI-C5-2 in toluene solution, and FIG. 6 is a kinetic profile of PDI-C5-2 in toluene solution.
As can be seen from FIG. 4, the basic state bleaching signal with a negative absorption peak at 545nm of PDI-C5-2 is substantially consistent with the appearance position of the maximum absorption peak of ultraviolet-visible absorption under a steady state condition, the wide basic state bleaching signal proves that strong coupling effect exists between molecules, and the negative absorption signal at 610nm is attributed to a stimulated emission signal, which is consistent with the signal of a fluorescence emission spectrum under the steady state condition. As can be seen from fig. 5, the signals of the ground state bleaching and stimulated emission do not decay completely within 7 nanoseconds, which is consistent with the time measured by the fluorescence lifetime. As can be seen from FIG. 1, the weak positive absorption band at 700-800nm width is the reabsorption signal of the excited state. As can be seen from FIGS. 4 to 6, in the solution state of PDI-C5-2 molecule, the decay pathway of singlet exciton is mainly fluorescence decay with time, and there is no other competing decay pathway, i.e., there is no singlet fission process of PDI-C5-2 in the solution state.
FIG. 7 is a three-dimensional spectrum of transient absorption of PDI-C5-1N in a toluene solution, FIG. 8 is a spectrum of transient absorption of PDI-C5-1N in a toluene solution, and FIG. 9 is a kinetic profile of PDI-C5-1N in a toluene solution.
As can be seen from FIG. 7, the absorption peak at 530nm is the ground state bleaching signal of PDI-C5-1N molecule, which is substantially consistent with the position of the maximum absorption peak of ultraviolet-visible absorption under steady state conditions, the broad ground state bleaching signal proves that strong coupling exists between molecules, and the signal attribution at 600nm is the stimulated emission signal, which is consistent with the signal of the fluorescence emission spectrum under steady state conditions. As can be seen from fig. 8, the signals of the ground state bleaching and stimulated emission do not decay completely within 7 nanoseconds, which is consistent with the time measured by the fluorescence lifetime. As can be seen from FIG. 7, the weak positive absorption band at 630-800nm width is the reabsorption signal in the excited state. As is clear from FIGS. 7 to 9, in the solution state of PDI-C5-1N molecule, the attenuation in the excited state is mainly fluorescence attenuation, i.e., radiation attenuation, and there is no other attenuation pathway. And no new long-lived component is seen over time, i.e., no singlet fission process exists in the solution state of PDI-C5-1N.
FIG. 10 is a three-dimensional spectrum of transient absorption of PDI-C5-2N in toluene solution, FIG. 11 is a spectrum of transient absorption of PDI-C5-2N in toluene solution, and FIG. 12 is a kinetic profile of PDI-C5-2N in toluene solution.
As can be seen from FIG. 10, the ground state bleaching signal with an absorption peak at 545nm of PDI-C5-2N is substantially consistent with the position where the maximum absorption peak of ultraviolet-visible absorption occurs under a steady state condition, and the broad ground state bleaching signal proves that strong coupling effect exists between molecules. Comparing the ultraviolet absorption spectrum and the fluorescence spectrum of the PDI-C5-2N molecule in the solution state, we can see that the position of the absorption peak is coincident with that of the emission peak, so that the ground state bleaching signal and the stimulated emission signal cannot be well distinguished in the transient absorption spectrum, which is consistent with the signal of the fluorescence emission spectrum in the steady state. As can be seen from fig. 11, the signals of the ground state bleaching and stimulated emission are not completely attenuated within 7 ns, which is consistent with the time measured by the fluorescence lifetime. As can be seen from FIG. 10, the weak positive absorption band at 600-800nm width is the reabsorption signal of the excited state. As can be seen from FIGS. 10 to 12, in the solution state of the PDI-C5-2N molecule, the excited state attenuation is mainly fluorescence attenuation, no other attenuation pathways exist, and no component similar to a triplet state or other long-life components appear, i.e., the process of singlet fission does not exist in the solution state of the PDI-C5-2N molecule.
FIG. 13 is a three-dimensional spectrum of transient absorption of PDI-C5-3 in a toluene solution, FIG. 14 is a spectrum of transient absorption of PDI-C5-3 in a toluene solution, and FIG. 15 is a kinetic profile of PDI-C5-3 in a toluene solution.
FIG. 16 is a three-dimensional spectrum of transient absorption of PDI-C5-4 in toluene solution, FIG. 17 is a spectrum of transient absorption of PDI-C5-4 in toluene solution, and FIG. 18 is a kinetic profile of PDI-C5-4 in toluene solution.
The PDI-C5-3 and PDI-C5-4 molecules have similar spectra as the other three molecules. According to the femtosecond transient absorption test of the perylene diimide derivative in the solution state, it can be obviously seen that in the solution state, signals appearing in a spectrogram only have signals of ground state bleaching, stimulated emission and excited state reabsorption, and no other components with long service life exist. The singlet excitons of the target product are directly attenuated in a fluorescence (radiation attenuation) mode, no other path is observed, the singlet splitting process only occurs in a thin film state, and in a solution state, the disorder presented among the molecules of the perylene diimide derivative weakens the coupling effect among the molecules, so that the perylene diimide derivative does not seem to have the singlet splitting process in the solution.
The application also provides a preparation method of the perylene diimide derivative, which comprises the following steps:
(1) preparation of N, N-pentane-perylene diimides
Uniformly mixing 3,4,9, 10-perylenetetracarboxylic anhydride, 3-aminopentane and imidazole, heating to 135-150 ℃ under the protection of inert gas until the imidazole is melted from a white solid into a colorless liquid, continuously reacting for 3-5 hours to obtain a solid after the reaction is finished, washing the solid with hydrochloric acid, methanol and water in sequence, drying, purifying and separating by using column chromatography, and obtaining a red solid N, N-N-pentane-perylene diimide with the yield of 80-90% by using dichloromethane as an eluent.
Optionally, the molar ratio of 3,4,9, 10-perylenetetracarboxylic anhydride, 3-aminopentane, and imidazole is 16-18: 41-45: 900-1200.
Optionally, washing 2-3 times each time.
(2) Preparation of 6, 12-dibromo-N, N-N-pentane-perylene diimide
Dissolving N, N-N-pentane-perylene diimide in dichloromethane, adding iodine simple substance, slowly and uniformly dropwise adding liquid bromine by using a constant-pressure dropping funnel to obtain a second mixture, reacting for 48-52 hours at 35-45 ℃ under the condition of tail gas treatment, cooling after the reaction is finished, adding a sodium bisulfite solution to remove unreacted bromine, sequentially extracting the solution by using dichloromethane and saturated saline water, drying by anhydrous sodium sulfate, spin-drying, separating by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 4:1, and red solid 6, 12-dibromo-N, N-N-pentane-perylene diimide is obtained, and the yield is 28-33%.
Optionally, the molar concentration of the N, N-pentane-perylene diimide in the second mixture is 0.066-0.075 mol/L, the molar concentration of the iodine simple substance is 0.005-0.007 mol/L, and the molar concentration of the liquid bromine is 4-4.4 mol/L.
Alternatively, the tail gas is treated by introducing the tail gas into an alkaline solution.
(3) Preparation of perylene diimide derivatives
When the perylene diimide derivative is PDI-C5-2:
dissolving 6, 12-dibromo-N, N-N-pentane-perylene diimide, tetrakistriphenylphosphine palladium, anhydrous potassium carbonate and 2-biphenylboronic acid in a solvent to obtain a first mixture, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas for reaction for 24-28 h, detecting that the raw materials are completely reacted basically by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting by adopting dichloromethane, water and saturated salt water to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and redundant water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 3:1, and a red solid PDI-C5-2 is obtained, and the yield is 35-40%.
Optionally, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033-0.044 mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009-0.0012 mol/L, the molar concentration of anhydrous potassium carbonate is 0.23-0.30 mol/L, and the molar concentration of 2-biphenylboronic acid is 0.16-0.22 mol/L.
Alternatively, the solvent comprises anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
When the perylene diimide derivative is PDI-C5-3:
dissolving 6, 12-dibromo-N, N-N-pentane-perylene diimide, tetrakistriphenylphosphine palladium, anhydrous potassium carbonate and 3-biphenylboronic acid in a solvent to obtain a first mixture, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas for reaction for 24-28 h, detecting that the raw materials are completely reacted basically by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting by adopting dichloromethane, water and saturated salt water to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and redundant water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 3:1, and red solid PDI-C5-3 is obtained, and the yield is 35-40%.
Optionally, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033-0.044 mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009-0.0012 mol/L, the molar concentration of anhydrous potassium carbonate is 0.23-0.30 mol/L, and the molar concentration of 3-biphenylboronic acid is 0.16-0.22 mol/L.
Alternatively, the solvent comprises anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
When the perylene diimide derivative is PDI-C5-4:
dissolving 6, 12-dibromo-N, N-pentane-perylene diimide, tetrakistriphenylphosphine palladium, anhydrous potassium carbonate and 4-biphenylboronic acid in a solvent to obtain a first mixture, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas for reaction for 24-28 h, detecting that the raw materials are completely reacted basically by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting by adopting dichloromethane, water and saturated salt water to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and redundant water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 3:1, and a red solid PDI-C5-4 is obtained, and the yield is 35-40%.
Optionally, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033-0.044 mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009-0.0012 mol/L, the molar concentration of anhydrous potassium carbonate is 0.23-0.30 mol/L, and the molar concentration of 4-biphenylboronic acid is 0.16-0.22 mol/L.
Alternatively, the solvent comprises anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
When the perylene diimide derivative is PDI-C5-1N:
dissolving 6, 12-dibromo-N, N-N-pentane-perylene diimide, tetrakistriphenylphosphine palladium, anhydrous potassium carbonate and alpha-naphthalene boric acid in a solvent to obtain a first mixture, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas for reaction for 24-28 h, detecting that the raw materials are completely reacted basically by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting by adopting dichloromethane, water and saturated salt water to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and redundant water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 3:1, and a red solid PDI-C5-1N is obtained, and the yield is 35-40%.
Optionally, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033-0.044 mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009-0.0012 mol/L, the molar concentration of anhydrous potassium carbonate is 0.23-0.30 mol/L, and the molar concentration of the alpha-naphthalene boric acid is 0.16-0.22 mol/L.
Alternatively, the solvent comprises anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
When the perylene diimide derivative is PDI-C5-2N:
dissolving 6, 12-dibromo-N, N-N-pentane-perylene diimide, tetrakistriphenylphosphine palladium, anhydrous potassium carbonate and beta-naphthalene boric acid in a solvent to obtain a first mixture, heating, refluxing and stirring at 125-135 ℃ under the protection of inert gas for reaction for 24-28 h, detecting that the raw materials are completely reacted basically by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting by adopting dichloromethane, water and saturated salt water to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and redundant water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, dichloromethane is 3:1, and a red solid PDI-C5-2N is obtained, and the yield is 35-40%.
Optionally, the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033-0.044 mol/L, the molar concentration of tetrakistriphenylphosphine palladium is 0.0009-0.0012 mol/L, the molar concentration of anhydrous potassium carbonate is 0.23-0.30 mol/L, and the molar concentration of the beta-naphthalene boric acid is 0.16-0.22 mol/L.
Alternatively, the solvent comprises anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
The application also provides an application of the perylene diimide derivative in preparation of photoelectric materials.
The perylene diimide derivative can also be applied to the fields of airport effect transistors, solar cells, industrial dyes and the like.
From the above, the perylene diimide derivative can generate singlet fission in a thin film state, and generate a high triplet level (1.10-1.28eV), so that the perylene diimide derivative can be applied to preparation of photoelectric materials.
The following examples are provided to further illustrate the perylene diimide derivatives of the present application, and the preparation method and applications thereof.
Example 1
The application provides a PDI-C5-2 and a preparation method thereof, which comprises the following steps:
(1) preparation of N, N-pentane-perylene diimides
Uniformly mixing 17mmol (6.73g) of 3,4,9, 10-perylene tetracarboxylic anhydride, 43mmol (3.74g) of 3-aminopentane and 1mol (69g) of imidazole, heating to 140 ℃ under the protection of inert gas until the imidazole is melted from a white solid into a colorless liquid, continuing to react for 4 hours to obtain a solid after the reaction is finished, washing the solid with hydrochloric acid, methanol and water in sequence, drying, purifying and separating by column chromatography, wherein an eluent is dichloromethane to obtain 8g of red solid, and the yield is 90%;
(2) preparation of 6, 12-dibromo-N, N-N-pentane-perylene diimide
Dissolving 6.65mmol (3g) of N, N-N-pentane-perylene diimide in 80mL of dichloromethane, adding 0.5mmol (0.13g) of iodine simple substance, slowly dropwise adding 339mmol (17.378mL) of liquid bromine by using a constant-pressure dropping funnel, uniformly mixing to obtain a second mixture, reacting for 48 hours at 40 ℃ under the condition of tail gas treatment, cooling after the reaction is finished, adding a sodium bisulfite solution to remove unreacted bromine, sequentially extracting the solution by using dichloromethane and saturated saline solution, drying by using anhydrous sodium sulfate, spin-drying, separating by using column chromatography silica gel chromatography, and using an eluent of petroleum ether, wherein dichloromethane is 4:1, so that 1.3g of red solid is obtained, and the yield is 28-33%;
(3) preparation of PDI-C5-2
Dissolving 0.726mmol (500mg) of 6, 12-dibromo-N, N-N-pentane-perylene diimide, 0.02mmol (23mg) of tetrakistriphenylphosphine palladium, 5mmol (690mg) of anhydrous potassium carbonate and 3.632mmol (719mg) of 2-biphenylboronic acid in 20mL of anhydrous toluene to obtain a first mixture, heating, refluxing and stirring the first mixture for reaction for 24 hours at 130 ℃ under the protection of inert gas, detecting that the raw materials are basically completely reacted by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting dichloromethane, water and saturated saline to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and excessive water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, and dichloromethane is 3:1, so that 250mg of red solid is obtained, the yield is 40%, and the red solid is PDI-C5-2.
Example 2
The application provides a PDI-C5-3 and a preparation method thereof, which comprises the following steps:
6, 12-dibromo-N, N-N-pentane-perylene diimide was prepared according to the method of example 1;
dissolving 0.726mmol (500mg) of 6, 12-dibromo-N, N-N-pentane-perylene diimide, 0.02mmol (23mg) of tetrakistriphenylphosphine palladium, 5mmol (690mg) of anhydrous potassium carbonate and 3.632mmol (719mg) of 3-biphenylboronic acid in 20mL of anhydrous toluene to obtain a first mixture, heating, refluxing and stirring the first mixture for reaction for 24 hours at 130 ℃ under the protection of inert gas, detecting that the raw materials are basically completely reacted by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting dichloromethane, water and saturated saline to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and excessive water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, and dichloromethane is 3:1, so that 250mg of red solid is obtained, the yield is 40%, and the red solid is PDI-C5-3.
Example 3
The application provides a PDI-C5-4 and a preparation method thereof, which comprises the following steps:
6, 12-dibromo-N, N-N-pentane-perylene diimide was prepared according to the method of example 1;
dissolving 0.726mmol (500mg) of 6, 12-dibromo-N, N-N-pentane-perylene diimide, 0.02mmol (23mg) of tetrakistriphenylphosphine palladium, 5mmol (690mg) of anhydrous potassium carbonate and 3.632mmol (719mg) of 4-biphenylboronic acid in 20mL of anhydrous toluene to obtain a first mixture, heating, refluxing and stirring the first mixture for reaction for 24 hours at 130 ℃ under the protection of inert gas, detecting that the raw materials are basically completely reacted by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting dichloromethane, water and saturated saline to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and excessive water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, and dichloromethane is 3:1, so that 250mg of red solid is obtained, the yield is 40%, and the red solid is PDI-C5-4.
Example 4
The application provides a PDI-C5-1N and a preparation method thereof, which comprises the following steps:
6, 12-dibromo-N, N-N-pentane-perylene diimide was prepared according to the method of example 1;
dissolving 0.726mmol (500mg) of 6, 12-dibromo-N, N-N-pentane-perylene diimide, 0.02mmol (23mg) of tetrakistriphenylphosphine palladium, 5mmol (690mg) of anhydrous potassium carbonate and 3.632mmol (614mg) of alpha-naphthalene boric acid in 20mL of anhydrous toluene to obtain a first mixture, heating, refluxing and stirring the first mixture for reaction for 24 hours at 130 ℃ under the protection of inert gas, detecting that the raw materials are basically completely reacted by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting dichloromethane, water and saturated saline to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and excessive water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, and dichloromethane is 3:1 to obtain a red solid, the yield is 40%, and the red solid is PDI-C5-1N.
Example 5
The application provides a PDI-C5-2N and a preparation method thereof, which comprises the following steps:
6, 12-dibromo-N, N-N-pentane-perylene diimide was prepared according to the method of example 1;
dissolving 0.726mmol (500mg) of 6, 12-dibromo-N, N-N-pentane-perylene diimide, 0.02mmol (23mg) of tetrakistriphenylphosphine palladium, 5mmol (690mg) of anhydrous potassium carbonate and 3.632mmol (614mg) of beta-naphthalene boric acid in 20mL of anhydrous toluene to obtain a first mixture, heating, refluxing and stirring the first mixture for reaction for 24 hours at 130 ℃ under the protection of inert gas, detecting that the raw materials are basically completely reacted by adopting a thin-layer chromatography dot plate, mainly generating two product dots, cooling, sequentially extracting dichloromethane, water and saturated saline to remove the tetrakistriphenylphosphine palladium, the potassium carbonate and excessive water, spin-drying, separating and purifying by using column chromatography silica gel chromatography, wherein an eluent is petroleum ether, and dichloromethane is 3:1, so that 250mg of red solid is obtained, the yield is 40%, and the red solid is PDI-C5-2N.
The foregoing is illustrative of the present application and is not to be construed as limiting thereof, as numerous modifications and variations will be apparent to those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims (10)

1. A perylene diimide derivative, wherein the structural formula of the perylene diimide derivative is as follows:
Figure FDA0002401903280000011
wherein R comprises ortho-biphenyl, meta-biphenyl, para-biphenyl, alpha-naphthalene or beta-naphthalene.
2. The perylene diimide derivative according to claim 1, wherein a fluorescence quantum yield of a thin film of the perylene diimide derivative is 6 to 22%.
3. The perylene diimide derivative according to claim 1, wherein a fluorescence quantum yield of a solution of the perylene diimide derivative is 50 to 85%.
4. The preparation method of the perylene diimide derivative according to any one of claims 1 to 3, wherein the preparation method of the perylene diimide derivative comprises the steps of heating, refluxing and stirring the first mixture at 125-135 ℃ for 24-28 hours under the protection of inert gas to prepare a crude perylene diimide derivative;
wherein the first mixture is prepared by the following method:
uniformly mixing 6, 12-dibromo-N, N-N-pentane-perylene diimide, palladium tetratriphenylphosphine, anhydrous potassium carbonate, a substituent and a solvent;
the substituent includes 2-biphenylboronic acid, 3-biphenylboronic acid, 4-biphenylboronic acid, alpha-naphthylboronic acid or beta-naphthylboronic acid.
5. The preparation method of the perylene diimide derivative according to claim 4, wherein the molar concentration of the 6, 12-dibromo-N, N-pentane-perylene diimide in the first mixture is 0.033 to 0.044mol/L, the molar concentration of the tetrakistriphenylphosphine palladium is 0.0009 to 0.0012mol/L, the molar concentration of the anhydrous potassium carbonate is 0.23 to 0.30mol/L, and the molar concentration of the substituent is 0.16 to 0.22 mol/L.
6. The method for preparing a perylene diimide derivative according to claim 4, wherein the solvent includes anhydrous toluene, chloroform, dichloromethane, tetrahydrofuran or N, N-dimethylformamide.
7. The preparation method of the perylene diimide derivative according to claim 6, wherein the preparation method of the perylene diimide derivative further comprises separation and purification, and the separation and purification comprises sequentially extracting the crude perylene diimide derivative with dichloromethane, water and saturated saline solution, drying by spinning, and then separating and purifying by column chromatography silica gel chromatography to obtain the perylene diimide derivative.
8. The method for preparing a perylene diimide derivative according to claim 5, wherein the 6, 12-dibromo-N, N-N-pentane-perylene diimide is prepared by the following method:
the preparation method comprises the steps of uniformly mixing N, N-pentane-perylene diimide, iodine simple substance, liquid bromine and dichloromethane to obtain a second mixture, and reacting the second mixture for 48-52 hours at 35-45 ℃.
9. The method for preparing a perylene diimide derivative according to claim 8, wherein the N, N-pentane-perylene diimide is prepared by:
uniformly mixing 3,4,9, 10-perylene tetracarboxylic anhydride, 3-aminopentane and imidazole, and reacting at 135-150 ℃ for 3-5 h under the protection of inert gas.
10. The use of the perylene diimide derivative according to any one of claims 1 to 3 in the preparation of optoelectronic materials.
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