阅读说明：本技术 一类三苯二噁嗪酰亚胺二倍体衍生物及制备方法 (Triphendioxazine imide diploid derivative and preparation method thereof ) 是由 陈令成 李萌 肖义 于 2021-02-22 设计创作，主要内容包括：一类三苯二噁嗪酰亚胺二倍体衍生物及制备方法,属于有机合成技术领域。该材料为具有大共轭且空间扭曲的三苯二噁嗪酰亚胺衍生物。它采用单溴代三苯二噁嗪酰亚胺,在铜粉的催化下,通过C-C单键偶联的方法合成得到。三苯二噁嗪酰亚胺二倍体半导体材料在常用有机溶剂中具有优良的溶解度,在可见光区域具有强吸收,较高的摩尔消光系数,还具有良好的氧化还原特性和电子传输性能,可以应用于有机光电领域。(A triphendioxazine imide diploid derivative and a preparation method thereof belong to the technical field of organic synthesis. The material is a triphendioxazine imide derivative with large conjugation and space distortion. The compound is synthesized by adopting monobromo triphenyl dioxazine imide and a C-C single bond coupling method under the catalysis of copper powder. The triphendioxazine imide diploid semiconductor material has excellent solubility in common organic solvents, strong absorption in a visible light region, higher molar extinction coefficient, good redox property and electron transmission performance, and can be applied to the field of organic photoelectricity.)

1. The triphendioxazine imide diploid derivative is characterized by having the following structural general formula:

wherein: r is independently selected from hydrogen atom, substituted or unsubstituted group, the substituted or unsubstituted group is alkyl with 1-60 carbon atoms, alkoxy with 1-60 carbon atoms, cycloalkyl with 3-60 carbon atoms, aryl with 5-60 carbon atoms, alkylaryl with 1-60 carbon atoms, alkylheteroaryl with 1-60 carbon atoms, alkylheterocyclic with 1-60 carbon atoms, alkyleneoxyalkyl with 1-60 carbon atoms, alkyleneoxyaryl with 1-60 carbon atoms, alkyleneoxyheteroaryl with 1-60 carbon atoms or alkyleneoxyheterocyclic with 1-60 carbon atoms.

2. The triphendioxazine imide diploid derivative of claim 1, wherein said substituted or unsubstituted groups are substituted or unsubstituted methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, Pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, tetracenyl, pentacenyl, hexacenyl, pyrenyl, indenyl, biphenyl, fluorenyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, thienyl, pyrrolyl, furyl, selenophenyl, silolyl, telluropheneyl, oxazolyl, pyridyl or pyrimidinyl.

3. The diploid triphendioxazine imide derivative as defined in claim 2, wherein the substituent is at least one of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, hydroxyl, mercapto, fluorine, chlorine, bromine, iodine, cyano, aldehyde, ester, sulfonic acid, sulfinic acid, nitro, amino, imino, carboxyl and hydrazine.

4. The preparation method of the triphendioxazine imide diploid derivative according to claim 1, wherein the triphendioxazine imide diploid derivative is obtained by mixing a compound A and Cu powder, adding an organic solvent, stirring and heating for reaction, and the reaction formula is as follows:

wherein, the definition of R is the same as that in the structural general formula.

5. The preparation method of the triphendioxazine imide diploid derivative according to claim 4, wherein the heating temperature of the preparation method is 90-180 ℃, the reaction time is 6-48 hours, and the dosage of Cu powder is 4-15 times of that of the compound A; the solvent is one or more of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, tetrahydrofuran, dioxane, nitrogen methyl pyrrolidone, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, sulfolane, acetonitrile and benzonitrile.

6. The application of the triphendioxazine imide diploid derivative according to claim 1, wherein the derivative is applied to the field of organic semiconductor materials as a photoelectric material.

Technical Field

The invention relates to a triphendioxazine imide diploid derivative and a preparation method thereof, belonging to the field of organic synthesis.

Background

The whole molecule of the triphendioxazine imide consists of a central triphendioxazine skeleton and dicarboxylic acid imides on two sides. Its advantages are: the organic semiconductor material has strong absorption in a visible light region, higher molar extinction coefficient, fluorescence quantum yield, good light stability and thermal stability and the like, and is an organic semiconductor material with excellent performance. The 6-position and the 14-position of the triphendioxazine imide are influenced by electron-withdrawing groups of the imide on two sides, the reactivity is strong, aromatic electrophilic substitution reaction is easy to occur, halogen can be introduced into the triphendioxazine imide, and more complex chemical modification is carried out on a parent body.

In 2017, the subject group designs and synthesizes a conjugate bridged triphendioxazine imide diploid structure, but the currently known triphendioxazine imide diploid structures all contain conjugate bridges for connection, the study on the triphendioxazine imide diploid structure directly connected by C-C single bonds is not involved, the diploid structure directly connected by the C-C single bonds can generate space torsion inhibition molecule aggregation, and the N-type semiconductor material with excellent photoelectric property is expected to be obtained through chemical modification on the structure. Therefore, how to develop a triphendioxazine imide diploid with directly connected C-C single bonds is challenging work, and the optical characteristics of the triphendioxazine imide diploid compound are worthy of being researched. To date, no triphendioxazine imide diploid derivatives involving direct linkage of the C-C bonds have been identified.

Disclosure of Invention

In order to solve the problems in the prior art, the invention provides a triphendioxazine imide diploid derivative and a preparation method thereof.

In order to realize the purpose of the invention, the invention adopts the following technical scheme: a triphendioxazine imide diploid derivative has the following structural general formula:

wherein: r is independently selected from hydrogen atom, substituted or unsubstituted group, the substituted or unsubstituted group is alkyl with 1-60 carbon atoms, alkoxy with 1-60 carbon atoms, cycloalkyl with 3-60 carbon atoms, aryl with 5-60 carbon atoms, alkylaryl with 1-60 carbon atoms, alkylheteroaryl with 1-60 carbon atoms, alkylheterocyclic with 1-60 carbon atoms, alkyleneoxyalkyl with 1-60 carbon atoms, alkyleneoxyaryl with 1-60 carbon atoms, alkyleneoxyheteroaryl with 1-60 carbon atoms or alkyleneoxyheterocyclic with 1-60 carbon atoms.

The group containing or not containing a substituent is a substituted or unsubstituted methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, decyloxy, tetradecyloxy, decyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, or decyloxy, Eicosyloxy, phenyl, naphthyl, anthracenyl, phenanthryl, tetracenyl, pentacenyl, hexacenyl, pyrenyl, indenyl, biphenyl, fluorenyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, undecyl, dodecylcycloalkyl, tridecylcycloalkyl, tetradecylcycloalkyl, pentadecyl, hexadecyl, heptadecyl, octadecylcycloalkyl, nonadecyl, eicosylcycloalkyl, thienyl, pyrrolyl, furyl, selenophenyl, silolyl, telluropheneyl, oxazolyl, pyridyl or pyrimidinyl groups, rings of the aforementioned heteroaryl groups fused with the rings of the aforementioned aryl groups derived groups or combinations of the aforementioned heteroaryl groups. These groups constituting the heteroaryl group may contain additional substituents.

The substituent is selected from the following groups: an alkyl group, preferably an alkyl group having 1 to 16 carbon atoms; alkoxy, preferably alkoxy having 1 to 16 carbon atoms; aryl, preferably having 5 to 16 carbon atoms; cycloalkyl groups, preferably those having 3 to 16 carbon atoms; a heterocyclic group, preferably having 5 to 16 carbon atoms, wherein the heterocyclic group contains heteroatoms selected from the group consisting of B, Si, O, Sn, N, S, P and Se; heteroaryl, in particular having 1 to 16 carbon atoms; heteroaralkyl, in particular consisting of an aryl group having from 5 to 16 carbon atoms and an alkyl moiety having from 1 to 16 carbon atoms; a heteroarylalkoxy group, preferably a heteroarylalkoxy group composed of an aryl group having 5 to 16 carbon atoms and an alkoxy group having 1 to 16 carbon atoms; alkenyl groups, particularly vinyl, allyl, 2-butenyl, 3-pentenyl, and the like; alkynyl, particularly propargyl, 3-pentynyl, and the like; amino substituents, particularly amino, methylamino, dimethylamino, and the like; acyl, preferably formyl, acetyl, benzoyl and the like; alkylthio groups, preferably methylthio groups, ethylthio groups, etc.; arylthio, particularly phenylthio and the like; heteroarylthio, particularly pyridylthio and the like; heterocyclic groups, preferably imidazolyl, pyridyl, etc.; a hydroxyl group; a halogen atom; a cyano group; an aldehyde group; an ester group; a sulfo group; a sulfino group; a nitro group; a carboxyl group; a hydrazine group. Most preferably, the substituent is at least one of a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a hydroxyl group, a mercapto group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, an aldehyde group, an ester group, a sulfonic group, a sulfinic acid group, a nitro group, an amino group, an imino group, a carboxyl group, and a hydrazine group.

The preparation method of the triphendioxazine imide diploid derivative comprises the steps of mixing a compound A and Cu powder, adding an organic solvent, stirring, heating and reacting to obtain the triphendioxazine imide diploid derivative, wherein the reaction is shown as the following formula:

wherein, the definition of R is the same as that in the structural general formula.

The heating temperature of the preparation method is 90-180 ℃, the reaction time is 6-48 hours, and the dosage of the Cu powder is 4-15 times of that of the compound A; the solvent is one or more of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, tetrahydrofuran, dioxane, nitrogen methyl pyrrolidone, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, sulfolane, acetonitrile and benzonitrile.

The triphendioxazine imide diploid derivative is applied to the fields of solar cells, organic light-emitting diodes and organic field effect transistors as a photoelectric material.

The invention has the beneficial effects that: the triphendioxazine imide diploid derivative provided by the invention initiatively synthesizes the triphendioxazine imide diploid directly connected by a C-C single bond, and the triphendioxazine imide diploid has the defect of easy accumulation of triphendioxazine imide molecules due to the existence of C-C single bond distortion, and has more excellent solubility. The derivative has high solubility in common organic solvents, is easy to dissolve in organic solvents such as dichloromethane, chloroform, toluene, chlorobenzene and the like, and has the solubility in dichloromethane of more than 60 mg/mL. Compared with other triphenyl dioxazine imide derivatives prepared based on noble metal catalyst (palladium metal coupling catalyst) coupling, the preparation method of the derivative is simple and efficient, only copper powder is used as the catalyst for heating reaction, no other conditions are needed, the reaction conditions are simpler, and the cost is lower. The derivative has very strong absorption peak and higher molar extinction coefficient in the visible light region of 300-650nm, and the molar extinction coefficient is as high as 1 x 10⁶ M^-1cm^-1Is far higher than other existing triphendioxazine imide derivatives. Meanwhile, the derivative has excellent light capture performance and shows the advantages of the derivative as an organic photoelectric material; the material isAlso has excellent oxidation-reduction characteristics and high electron accepting capability, and the LUMO energy level is measured and calculated by cyclic voltammetry to be between-3.9 eV and-4.0 eV. Based on the excellent photoelectric properties, the derivatives have great application prospects in solar cells, light-emitting diodes and organic field effect transistors.

Drawings

FIG. 1 is a diagram showing an ultraviolet-visible absorption spectrum of a 6-undecamide-derived triphendioxazine imide diploid.

FIG. 2 is a cyclic voltammogram of a 6-undecamide-derivatized triphendioxazine imide diploid.

Detailed Description

In order to make the technical solutions of the present invention clearer, the technical solutions in the following embodiments will be clearly and completely described with reference to the embodiments of the present invention, which are used for illustrating the present invention and are not intended to limit the scope of the present invention.

Example 1

1g of brominated triphendioxazine imide and 987.52mg of Cu powder are weighed into a reaction bottle, 25ml of dimethyl sulfoxide is added, and the mixture is stirred and reacted for 18 hours at 120 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.4g of a product with the yield of 45 percent, wherein the HRMS is found in the mount 1127.1800.

Example 2

1g of brominated triphendioxazine imide and 782.76mg of Cu powder are weighed into a reaction bottle, 25ml of dimethyl sulfoxide is added, and the reaction is stirred at 110 ℃ for 15 hours. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.5g of a product, wherein the yield is 55%, and the HRMS is found in found 1463.8280.

Example 3

1g of brominated triphendioxazine imide and 782.76mg of Cu powder are weighed into a reaction bottle, 25ml of azomethylpyrrolidone is added, and the mixture is stirred and refluxed for 8 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.45g of a product with the yield of 49 percent, HRMS (Rockwell Mass Spectrometry) and found 1688.2600.

Example 4

The synthesis method is referred to example 3.

Example 5

1g of brominated triphendioxazine imide and 540.92mg of Cu powder are weighed into a reaction bottle, 25ml of tetrahydrofuran is added, and the mixture is stirred and refluxed for 20 hours at 70 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.25g of a product with the yield of 29 percent, wherein the HRMS is found in found 1014.9640.

Example 6

1g of brominated triphendioxazine imide and 774.40mg of Cu powder are weighed into a reaction bottle, 25ml of toluene is added, and the mixture is stirred and refluxed for 9 hours at 120 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.35g of a product with the yield of 40 percent, wherein the HRMS is found in found 1071.0720.

Example 7

1g of brominated triphendioxazine imide and 1.48g of Cu powder are weighed into a reaction bottle, 25ml of 1, 4-dioxane is added, and the mixture is stirred and refluxed for 15 hours at the temperature of 110 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.3g of a product with the yield of 34 percent, wherein the HRMS is found in found 1127.1800.

Example 8

1g of brominated triphendioxazine imide and 1.48g of Cu powder are weighed into a reaction bottle, 25ml of N, N-dimethylformamide is added, and the mixture is stirred and refluxed for 6 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.4g of a product with the yield of 45 percent, wherein the HRMS is found in the mount 1337.5850.

Example 9

1g of brominated triphendioxazine imide and 709.70mg of Cu powder are weighed into a reaction bottle, 25ml of dimethylbenzene is added, and the mixture is stirred and refluxed for 10 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.25g of a product with the yield of 28 percent, wherein the HRMS is found in found 1183.2880.

Example 10

1g of brominated triphendioxazine imide and 648.62mg of Cu powder are weighed into a reaction bottle, 25ml of chlorobenzene is added, and stirring reflux is carried out for 15 hours at 130 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.4g of a product with the yield of 44 percent, wherein the HRMS is found in found 1407.7200.

Example 11

1g of brominated triphendioxazine imide and 648.62mg of Cu powder are weighed into a reaction bottle, 25ml of dimethylacetamide is added, and stirring and refluxing are carried out at 165 ℃ for 12 hours. After the reaction is completed, the reaction solution is dried by spinning under reduced pressure, and the product of 0.38g is obtained by column chromatography separation, the yield is 43 percent, and the HRMS is found in found 1151.0320.

Example 12

1g of brominated triphendioxazine imide and 462.86mg of Cu powder are weighed into a reaction bottle, 25ml of toluene is added, and the mixture is stirred and refluxed for 8 hours at 120 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.36g of a product with the yield of 27 percent, wherein the HRMS is found in the found 1487.6800.

Example 13

1g of brominated triphendioxazine imide and 462.86mg of Cu powder are weighed into a reaction bottle, 25ml of DMF is added, and the mixture is stirred and refluxed for 8 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.31g of a product with the yield of 34 percent, wherein the HRMS is found in found 1331.0200.

Example 14

1g of brominated triphendioxazine imide and 462.86mg of Cu powder are weighed into a reaction bottle, 25ml of dimethylacetamide is added, and stirring and refluxing are carried out at 165 ℃ for 16 hours. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.31g of a product with the yield of 34 percent, wherein the HRMS is found in found 1331.0200.

Example 15

1g of brominated triphendioxazine imide and 781.82mg of Cu powder are weighed into a reaction bottle, 25ml of tetrahydrofuran is added, and the mixture is stirred and refluxed for 10 hours at 70 ℃. After the reaction is completed, the reaction solution is dried by spinning under reduced pressure, and the product of 0.3g is obtained by column chromatography separation, the yield is 33 percent, and the HRMS is found in found 1303.2280.

Example 16

1g of brominated triphendioxazine imide and 679.84mg of Cu powder are weighed into a reaction bottle, 25ml of hexamethylphosphoramide is added, and the mixture is stirred and refluxed for 10 hours at 130 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.4g of a product with the yield of 44 percent, wherein the HRMS is found in found 1311.1320.

Example 17

1g of brominated triphendioxazine imide and 672.85mg of Cu powder are weighed into a reaction bottle, 25ml of acetonitrile is added, and the mixture is stirred and refluxed for 15 hours at 90 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.4g of a product with the yield of 44 percent, wherein the HRMS is found in found 1311.1320.

Example 18

1g of brominated triphendioxazine imide and 929.75mg of Cu powder are weighed into a reaction bottle, 25ml of chlorobenzene is added, and stirring reflux is carried out for 15 hours at 130 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.35g of a product, wherein the yield is 39%, and the HRMS is found in found 1207.1400.

Example 19

1g of brominated triphendioxazine imide and 761.64mg of Cu powder are weighed into a reaction bottle, 25ml of toluene is added, and the mixture is stirred and refluxed for 10 hours at 120 ℃. After the reaction is completed, the reaction solution is dried by spinning under reduced pressure, and the product of 0.33g is obtained by column chromatography separation, the yield is 37 percent, and the HRMS is found in found 1175.1200.

Example 20

1g of brominated triphendioxazine imide and 869.97mg of Cu powder are weighed into a reaction bottle, 25ml of DMF is added, and the mixture is stirred and refluxed for 12 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.28g of a product with the yield of 32 percent, wherein the HRMS is found in found 1154.9840.

Example 21

1g of brominated triphendioxazine imide and 951.98mg of Cu powder are weighed into a reaction bottle, 25ml of dichlorobenzene is added, and the mixture is stirred and refluxed for 14 hours at the temperature of 140 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction solution, and carrying out column chromatography separation to obtain 0.34g of a product with the yield of 38 percent, wherein the HRMS is found in found 1175.2240.

Example 22

1g of brominated triphendioxazine imide and 728.79mg of Cu powder are weighed into a reaction bottle, 25ml of dimethyl sulfoxide is added, and the mixture is stirred and refluxed for 16 hours at 110 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.35g of a product, wherein the yield is 39%, and the HRMS is found in found 1235.2840.

Example 23

1g of brominated triphendioxazine imide and 940.74mg of Cu powder are weighed into a reaction bottle, 25ml of toluene is added, and the mixture is stirred and refluxed for 10 hours at 110 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.3g of a product with the yield of 34 percent, wherein the HRMS is found in found 1191.1760.

Example 24

1g of brominated triphendioxazine imide and 434.35mg of Cu powder are weighed into a reaction bottle, 25ml of tetrahydrofuran is added, and the mixture is stirred and refluxed for 10 hours at 70 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.2g of a product with the yield of 23 percent, wherein the HRMS is found in found 1275.2500.

Example 25

1g of brominated triphendioxazine imide and 434.35mg of Cu powder are weighed into a reaction bottle, 25ml of dioxane is added, and the mixture is stirred and refluxed for 10 hours at 110 ℃. And (3) after the reaction is completed, carrying out decompression spin-drying on the reaction liquid, and carrying out column chromatography separation to obtain 0.2g of a product with the yield of 23 percent, wherein the HRMS is found in found 1275.2500.

Example 26

The 6-undecamide-derived triphendioxazine imide diploid (compound B2) obtained in example 2 was subjected to property studies.

UV-Vis spectra of 6-undecamide-derived triphendioxazine imide diploids were measured using an apparatus model U.S. HP8543 UV spectrophotometer, with a concentration of 1.0X 10 of Compound B2 first formulated^-3 Adding dichloromethane solution into the mother liquor of mol/L to dilute the mother liquor to 1.0X 10^-5 And (5) determining the ultraviolet visible absorption spectrum of the solution in mol/L. As shown in FIG. 1, the material has very strong absorption in the visible light region of 300-600nm, and the maximum absorption peak is 537 nm. The molar extinction coefficient of the material is calculated by using the formula A = epsilon bc, and the molar extinction coefficient is calculated to be 125000M^-1cm^-1(in the formula, A is absorbance, b is the thickness of the sample cell, and c is the amount concentration of the substance.). According to the formulaTo find the optical band gapE _g Is 1.83 eV. The material is proved to have excellent light trapping performance. Meanwhile, certain distortion exists between conjugate planes of the diploid, which is beneficial to inhibiting intermolecular aggregation and is contained in dichloromethaneThe solubility of the compound is more than 60mg/mL, and the solubility of the compound is greatly superior to that of monomer triphendioxazine imide.

Example 27

Cyclic voltammetry was performed on the 6-undecamine-derived triphendioxazine imide diploid derivative obtained in example 2, using a BSA100B/W electrochemical analysis system as an instrument model, using a three-electrode test system, a glassy carbon electrode as a working electrode, a saturated calomel electrode as a reference electrode, a platinum wire electrode as a comparison electrode, accurately weighing and preparing a compound B2 into a10 mg/ml dichloromethane solution, adding tetrabutylammonium hexafluorophosphate as an electrolyte, and measuring a cyclic voltammetry curve thereof as shown in fig. 2, wherein the compound has three groups of reversible redox peaks. Can accept three electrons, and compared with other derivatives, the material has stronger electron accepting capability. The initial potential of the first reduction peak of the material obtained from the cyclic voltammetry is-0.585 eV, ferrocene is used as an internal standard couple, and the absolute value of the ferrocene couple relative to vacuum is 4.8eV according to the formulaAnd the LUMO level was calculated to be-3.91 eV. According to the formulaThe HOMO energy level was calculated to be-5.74 eV. The material was demonstrated to have good redox properties.

Example 28

The spectral properties, electrochemical properties and solubility data of compounds B8, B13, B15, B17, B19, B23 and B25 are given in table form, the method for testing the spectral properties is the same as in example 26, the method for testing the electrochemical properties is the same as in example 27, and the specific data are shown in the following table:

compound (I)	Molar extinction coefficient	Solubility in methylene chloride	Logarithm of redox peak
				B8	110000M-1cm-1	Greater than 60mg/mL	3 pairs of
B13	105000M-1cm-1	Greater than 60mg/mL	3 pairs of
				B15	112000M-1cm-1	Greater than 60mg/mL	3 pairs of
B17	102000M-1cm-1	Greater than 60mg/mL	3 pairs of
				B19	106000M-1cm-1	Greater than 60mg/mL	3 pairs of
B23	120000M-1cm-1	Greater than 60mg/mL	3 pairs of
				B25	122000M-1cm-1	Greater than 60mg/mL	3 pairs of

As can be seen from the data in the table, compounds B8, B13, B15, B17, B19, B23 and B25 also have excellent light trapping properties, higher solubility and good redox properties.

The above description is only a preferred embodiment of the present invention, and should not be taken as limiting the invention in any way, and it will be understood by those skilled in the art that the present invention may be embodied in many different forms without departing from the spirit or scope of the present invention.