CN104974173A - Preparation method of bay-bit embedded pentabasic sulfur heterocycle and hexahydric oxygen heterocycle 3,4:9,10-perylene tetracarboxylic n-butyl acrylate - Google Patents
Preparation method of bay-bit embedded pentabasic sulfur heterocycle and hexahydric oxygen heterocycle 3,4:9,10-perylene tetracarboxylic n-butyl acrylate Download PDFInfo
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- CN104974173A CN104974173A CN201510308613.6A CN201510308613A CN104974173A CN 104974173 A CN104974173 A CN 104974173A CN 201510308613 A CN201510308613 A CN 201510308613A CN 104974173 A CN104974173 A CN 104974173A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Abstract
The present invention discloses a preparation method of bay-bit embedded pentabasic sulfur heterocycle and hexahydric oxygen heterocycle 3,4:9,10-perylene n-butyl tetracarboxylate. The method comprises the steps of: dissolving bay-bit mononitration-3,4:9,10-perylene n-butyl tetracarboxylate in N-methylpyrrolidone, reacting with elemental sulfur to obtain an intermediate product bay-bit embedded pentabasic sulfur heterocycle-3,4:9,10-perylene n-butyl tetracarboxylate; further nitrating the intermediate product to obtain the bay-bit mononitration single sulfur ring perylene n-butyl tetracarboxylate; and reacting the bay-bit mononitration single sulfur ring perylene n-butyl tetracarboxylate with an acid-binding agent and a nucleophilic reagent capable of forming carbanion to obtain the desired product bay-bit embedded pentabasic sulfur heterocycle and hexahydric oxygen heterocycle 3,4:9,10-perylene n-butyl tetracarboxylate. The bay-bit embedded pentabasic sulfur heterocycle and hexahydric oxygen heterocycle 3,4:9,10-perylene n-butyl tetracarboxylate prepared by the invention employs different annulations at two sides of the bay-bit, substantially enlarges the molecular conjugated system, enhances molecular flatness, and can select different substituents to change intramolecular charge distribution, so as to tune electronic structure and photophysical property of the molecule.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to the preparation method of position, a kind of gulf embedding pentatomic sulphur heterocycle and the positive butyl ester of hexa-atomic oxa-ring-3,4:9,10-perylene tetracarboxylic acid.
Background technology
Perylene tetracarboxylic acid positive butyl ester analog derivative has good electron acceptability, high fluorescence quantum yield, the photo and thermal stability of height, unique photoelectric property and redox property and is widely used in the sciemtifec and technical spheres such as organic field effect tube, photochromic material, extinction array, organic solar batteries, photodiode and color liquid crystal strainer, is the organic dye with high utility value that a class is generally acknowledged.Therefore Dui perylene tetracarboxylic acid positive butyl ester compounds carries out derivative reaction and becomes particularly important, at this wherein, ring expansion can increase the conjugated pi system of large perylene system derivative, thus the photoelectric properties of this analog derivative tuning effectively, be a kind of important derivatization method.Current ， perylene system derivative ring expansion basic need carries out cyclisation under illumination condition or metal catalytic effect, two kinds of methods all relative complex.
Summary of the invention
The object of this invention is to provide the preparation method of position, a kind of gulf embedding pentatomic sulphur heterocycle and the positive butyl ester of hexa-atomic oxa-ring-3,4:9,10-perylene tetracarboxylic acid, the method has that synthesis step is simple, raw material is easy to get, productive rate advantages of higher.
In order to solve above technical problem, the technical solution used in the present invention is:
The preparation method of a kind of position, gulf embedding pentatomic sulphur heterocycle and the positive butyl ester of hexa-atomic oxa-ring-3,4:9,10-perylene tetracarboxylic acid, comprises the steps:
(1) be dissolved in solvent by position, the gulf positive butyl ester of mono-nitration-3,4:9,10-perylene tetracarboxylic acid, add sulphur powder, protection of inert gas, reaction, obtains the positive butyl ester of position, intermediate product gulf embedding pentatomic sulphur heterocycle-3,4:9,10-perylene tetracarboxylic acid;
(2) position, the gulf positive butyl ester of embedding pentatomic sulphur heterocycle-3,4:9,10-perylene tetracarboxylic acid obtained in step (1) is carried out nitrated, obtain the positive butyl ester of position, gulf mono-nitration list Liu Huan perylene tetracarboxylic acid;
(3) position, the gulf positive butyl ester of mono-nitration list Liu Huan perylene tetracarboxylic acid obtained in step (1) is dissolved in solvent, add acid binding agent, add the nucleophilic reagent of carbanion, react 0.5 ~ 1 hour, obtain position, target product gulf embedding pentatomic sulphur heterocycle and hexa-atomic oxa-ring-3, the positive butyl ester of 4:9,10-perylene tetracarboxylic acid.
Preferably, in step (1), reaction process is followed the tracks of by tlc.Follow the tracks of reaction process, judge that degree is carried out in reaction by it, when having reacted, terminate reaction in time.
Preferably, in step (1), the temperature of described reaction is 110 ~ 120 DEG C, and the time of reaction is 4 ~ 6 hours.
Preferably, in step (1), the ratio of the amount of substance of position, the gulf positive butyl ester of mono-nitration-3,4:9,10-perylene tetracarboxylic acid and sulphur powder is 1:10-30, and the consumption of solvent is that the positive butyl ester of every gram of mono-nitration-3,4:9,10-perylene tetracarboxylic acid uses 10-200 milliliter.
Preferably, in step (1), described solvent is N-Methyl pyrrolidone, DMF or dimethyl sulfoxide (DMSO).
Preferably, in step (1), described rare gas element is argon gas or nitrogen.
Preferably, in step (1), described purifying carries out separation and purification by chromatographic column.
Preferably, in step (3), described acid binding agent is Anhydrous potassium carbonate, triethylamine or pyridine.
Preferably, in step (3), the described nucleophilic reagent that can form carbanion is nitropropane, dibromo fluorenes or diethyl malonate.
Preferably, in step (3), the mol ratio that the nucleophilic reagent of the positive butyl ester of position, gulf mono-nitration list Liu Huan perylene tetracarboxylic acid, acid binding agent and carbanion adds is 1:1-10:1-20.
Preferably, in step (3), the positive butyl ester of described every gram of mono-nitration list Liu Huan perylene tetracarboxylic acid uses solvent 10-200 milliliter.
In step (2), nitrated method, comprise the steps: to add (70 milligrams in 50 milliliters of round-bottomed flasks, 0.1 mmole) the embedding pentatomic sulphur heterocycle-3 in position, gulf, 4:9, the positive butyl ester of 10-perylene tetracarboxylic acid, using 20 milliliters of methylene dichloride as solvent, nitrosonitric acid 1 milliliter is dropwise dripped under 30 ~ 35 DEG C of conditions, concentration 86% ~ 97.5%), reaction (the embedding pentatomic sulphur heterocycle-3 of position, product gulf mono-nitration is followed the tracks of by tlc, 4:9, the positive butyl ester of 10-perylene tetracarboxylic acid is red-brown unstressed configuration, the embedding pentatomic sulphur heterocycle-3 in position, reactant gulf, 4:9, the positive butyl ester of 10-perylene tetracarboxylic acid is that yellow has yellow-green fluorescence, the carrying out of reaction can well be followed the tracks of) by tlc.After reaction terminates, reaction solution is added unsaturated carbonate aqueous solutions of potassium 10 milliliters, separate organic layer, remove solvent, obtain thick product.Thick product carries out silica gel column chromatography (leacheate is methylene dichloride: ethyl acetate=20:1), obtains brown-red solid 63 milligrams (productive rate is 85%).
Synthetic route of the present invention is:
The invention provides the preparation method of position, a class gulf embedding pentatomic sulphur heterocycle and the positive butyl ester of hexa-atomic Yang Za Huan perylene tetracarboxylic acid, with position, gulf mono-nitration 3,4:9, the positive butyl ester of 10 perylene tetracarboxylic acid is raw material, target product is obtained through three-step reaction, expand perylene tetracarboxylic acid positive butyl ester class derivative reaction, provide an effective ring expansion method.
Advantageous Effects of the present invention is:
(1) position, the gulf embedding pentatomic sulphur heterocycle prepared in the present invention and the positive butyl ester of hexa-atomic Yang Za Huan perylene tetracarboxylic acid, both sides, position, gulf adopt different annulations, expand the conjugated system of molecule significantly, enhancing planes of molecules, intramolecular electric charge substep can be changed thus tuning electronic structure of molecule, photophysical property by choosing different substituents.This structure system new discovery structure, has enriched the derivatization method of this compounds simultaneously;
(2) reaction conditions is gentle, and reactions steps is simple; Productive rate is comparatively up to more than 50%.
(3) advantage of the selection of each step reagent and treatment process: select rare gas element argon shield reaction in step (1), effectively can completely cut off air, prevent the oxygen in air from impacting generation by product to reaction at relatively high temperatures.
Select using N-Methyl pyrrolidone, DMF or dimethyl sulfoxide (DMSO) as solvent in step (1), to this type of reaction parent and derivative solvability is good and aftertreatment is simple and convenient.
Nitrifying method described in step (2), the gentle productive rate of reaction conditions is high, and compared with common single bromination reaction intermediate, mononitrated product productive rate is higher and subsequent reactions facilitates mild condition.
Described in step (3) using Anhydrous potassium carbonate, triethylamine or pyridine as acid binding agent, can in time generate acid product in neutralization reaction and not participate in main reaction; Described nucleophilic reagent can form carbanion in the basic conditions fast, and the carbanion affinity formed is strong, and reaction is fast.
Accompanying drawing explanation
The mass spectrum of Fig. 1 product A;
The nucleus magnetic hydrogen spectrum of Fig. 2 product A;
The mass spectrum of Fig. 3 product B;
The nucleus magnetic hydrogen spectrum of Fig. 4 product B;
The mass spectrum of Fig. 5 product C;
The nucleus magnetic hydrogen spectrum of Fig. 6 product C.
Embodiment
Below in conjunction with the drawings and specific embodiments, the invention will be further described.
The described positive butyl ester of 3,4:9,10-perylene tetracarboxylic acid is synthesized with method described in following document by 3,4:9,10-perylenetetracarboxylic dianhydride.Xiong Mo,Min-Min Shi,Jia-Chi Huang,Mang Wang,Hong-Zheng Chen.Synthesis,aggregationand photoconductive properties of alkoxycarbonyl substituted perylenes.Dyes and Pigments 2008；76(1):236-242.
Perylenetetracarboxylic dianhydride and carbanion nucleophilic reagent (purchased from: this biochemical technology company limited of Tianjin Skien).
Embodiment 1
(1) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, gulf Za Huan perylene tetracarboxylic acid:
In 25 milliliters of round-bottomed flasks, add 40 milligrams of (1.25 mmole) sulphur powder, 8 milliliters of N-Methyl pyrrolidone (NMP), stir 10 minutes at 90 DEG C.Add 50 milligrams of positive butyl esters of (0.073 mmole) single Xiaoization perylene tetracarboxylic acid under argon shield, react 6 hours at 110 DEG C, follow the tracks of reaction by tlc.By in reaction solution impouring 100 ml water after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain intermediate product 35 milligrams (0.051 mmole, productive rate is about 70%).
(2) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, mono-nitration gulf Za Huan perylene tetracarboxylic acid:
70 milligrams of positive butyl esters of (0.1 mmole) position, gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are added in 25 milliliters of round-bottomed flasks, 10 milliliters of methylene dichloride, nitrosonitric acid 1 milliliter is dropwise dripped under 30 DEG C of conditions, concentration 86% ~ 97.5%), room temperature reaction 1 hour, follows the tracks of reaction by tlc.Add 5 milliliters of unsaturated carbonate aqueous solutions of potassium termination reactions after reaction terminates, after organic layer washed with water, dried over mgso is spent the night, and removes solvent and obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain the positive butyl ester of position, mono-nitration gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid 63 milligrams (0.085 mmole, productive rate is 85%), carry out following reaction as raw material.
(3) preparation of product A:
In 25 milliliters of round-bottomed flasks, 50 milligrams of (0.069 mmole) position, mono-nitration gulf positive butyl esters of embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are dissolved in 8 milliliters of NMP, add 60 milligrams of (0.434 mmole) Anhydrous potassium carbonates, dropwise drip nitropropane 0.1 milliliter (being about 0.7 mmole), room temperature reaction 1 hour, follows the tracks of reaction by tlc.By in the aqueous hydrochloric acid of reaction solution impouring 100 milliliter 10% after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtain thick product, thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain product A (structural characterization is shown in Fig. 1 and Fig. 2) 32 milligrams (0.044 mmole, productive rate is about 64%).The structural formula of product A is:
These both sides, position, series derivates gulf adopt different annulations, expand the conjugated system of molecule significantly, enhancing planes of molecules, intramolecular electric charge substep can be changed thus tuning electronic structure of molecule, photophysical property by choosing different substituents.This structure system new discovery structure, has enriched the derivatization method of this compounds simultaneously.
Embodiment 2
(1) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, gulf Za Huan perylene tetracarboxylic acid:
In 25 milliliters of round-bottomed flasks, add 40 milligrams of (1.25 mmole) sulphur powder, 10 milliliters of DMFs, stir 10 minutes at 90 DEG C.Add 50 milligrams of positive butyl esters of (0.073 mmole) single Xiaoization perylene tetracarboxylic acid under nitrogen protection, react 5 hours at 120 DEG C, follow the tracks of reaction by tlc.By in reaction solution impouring 100 ml water after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain intermediate product 35 milligrams (0.051 mmole, productive rate is about 70%).
(2) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, mono-nitration gulf Za Huan perylene tetracarboxylic acid:
70 milligrams of positive butyl esters of (0.1 mmole) position, gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are added in 25 milliliters of round-bottomed flasks, 10 milliliters of methylene dichloride, nitrosonitric acid 1 milliliter is dropwise dripped under 30 DEG C of conditions, concentration 86% ~ 97.5%), room temperature reaction 1 hour, follows the tracks of reaction by tlc.Add 5 milliliters of unsaturated carbonate aqueous solutions of potassium termination reactions after reaction terminates, after organic layer washed with water, dried over mgso is spent the night, and removes solvent and obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain the positive butyl ester of position, mono-nitration gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid 63 milligrams (0.085 mmole, productive rate is 85%), carry out following reaction as raw material.
(3) preparation of product B:
In 25 milliliters of round-bottomed flasks, 50 milligrams of (0.069 mmole) position, mono-nitration gulf positive butyl esters of embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are dissolved in 10 milliliters of N-Methyl pyrrolidone (NMP), add 60 milligrams of (0.434 mmole) Anhydrous potassium carbonates, add 200 milligrams of (being about 0.7 mmole) dibromo fluorenes, room temperature reaction 0.5 hour, follows the tracks of reaction by tlc.By in the aqueous hydrochloric acid of reaction solution impouring 100 milliliter 10% after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtain thick product, thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain product B (structural characterization is shown in Fig. 3 and Fig. 4) 40 milligrams (0.04 mmole, productive rate is about 58%).The structural formula of product B is:
Embodiment 3
(1) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, gulf Za Huan perylene tetracarboxylic acid:
In 25 milliliters of round-bottomed flasks, add 40 milligrams of (1.25 mmole) sulphur powder, 8 milliliters of dimethyl sulfoxide (DMSO), stir 10 minutes at 90 DEG C.Add 50 milligrams of positive butyl esters of (0.073 mmole) single Xiaoization perylene tetracarboxylic acid under argon shield, react 4 hours at 120 DEG C, follow the tracks of reaction by tlc.By in reaction solution impouring 100 ml water after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain intermediate product 35 milligrams (0.051 mmole, productive rate is about 70%).
(2) preparation of the positive butyl ester of the embedding pentatomic sulphur in position, mono-nitration gulf Za Huan perylene tetracarboxylic acid:
70 milligrams of positive butyl esters of (0.1 mmole) position, gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are added in 25 milliliters of round-bottomed flasks, 10 milliliters of methylene dichloride, nitrosonitric acid 1 milliliter is dropwise dripped under 30 ~ 35 DEG C of conditions, concentration 86% ~ 97.5%), room temperature reaction 0.8 hour, follows the tracks of reaction by tlc.Add 5 milliliters of unsaturated carbonate aqueous solutions of potassium termination reactions after reaction terminates, after organic layer washed with water, dried over mgso is spent the night, and removes solvent and obtains thick product.Thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain the positive butyl ester of position, mono-nitration gulf embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid 63 milligrams (0.085 mmole, productive rate is 85%), carry out following reaction as raw material.
(3) preparation of product C:
In 25 milliliters of round-bottomed flasks, 50 milligrams of (0.069 mmole) position, mono-nitration gulf positive butyl esters of embedding pentatomic sulphur Za Huan perylene tetracarboxylic acid are dissolved in 8 ~ 10 milliliters of N, in dinethylformamide, add 60 milligrams of (0.434 mmole) Anhydrous potassium carbonates, dropwise drip diethyl malonate 0.1 milliliter (being about 0.7 mmole), room temperature reaction 0.8 hour, follows the tracks of reaction by tlc.By in the aqueous hydrochloric acid of reaction solution impouring 100 milliliter 10% after reaction terminates, separate out precipitation, standing, decompress filter, filter cake 10% aqueous ethanolic solution washing 2 ~ 3 times, by the solid vacuum-drying of collecting, obtain thick product, thick product carries out silica gel column chromatography, and leacheate is methylene dichloride: ethyl acetate=20:1.Obtain product C (structural characterization is shown in Fig. 5 and Fig. 6) 31 milligrams (0.036 mmole, productive rate is about 52%).Product C structural formula is:
By reference to the accompanying drawings the specific embodiment of the present invention is described although above-mentioned; but the restriction not to invention protection domain; one of ordinary skill in the art should be understood that; on the basis of technical scheme of the present invention, those skilled in the art do not need to pay various amendment or distortion that creative work can make still in protection scope of the present invention.
Claims (10)
1. the preparation method of position, a gulf embedding pentatomic sulphur heterocycle and the positive butyl ester of hexa-atomic oxa-ring-3,4:9,10-perylene tetracarboxylic acid, comprises the steps:
(1) be dissolved in solvent by position, the gulf positive butyl ester of mono-nitration-3,4:9,10-perylene tetracarboxylic acid, add sulphur powder, protection of inert gas, reaction, obtains the positive butyl ester of position, intermediate product gulf embedding pentatomic sulphur heterocycle-3,4:9,10-perylene tetracarboxylic acid;
(2) position, the gulf positive butyl ester of embedding pentatomic sulphur heterocycle-3,4:9,10-perylene tetracarboxylic acid obtained in step (1) is carried out nitrated, obtain the positive butyl ester of position, gulf mono-nitration list Liu Huan perylene tetracarboxylic acid;
(3) position, the gulf positive butyl ester of mono-nitration list Liu Huan perylene tetracarboxylic acid obtained in step (1) is dissolved in solvent, add acid binding agent, add the nucleophilic reagent of carbanion, react 0.5 ~ 1 hour, obtain position, target product gulf embedding pentatomic sulphur heterocycle and hexa-atomic oxa-ring-3, the positive butyl ester of 4:9,10-perylene tetracarboxylic acid.
2. preparation method according to claim 1, is characterized in that: in step (1), and the temperature of described reaction is 110 ~ 120 DEG C, and the time of reaction is 4 ~ 6 hours.
3. preparation method according to claim 1, it is characterized in that: in step (1), position, gulf mono-nitration-3,4:9, the mol ratio of the positive butyl ester of 10-perylene tetracarboxylic acid and sulphur powder is 1:10-30, the consumption of solvent is that the positive butyl ester of every gram of mono-nitration-3,4:9,10-perylene tetracarboxylic acid uses 10-200 milliliter.
4. preparation method according to claim 1, is characterized in that: in step (1), and described solvent is N-Methyl pyrrolidone, DMF or dimethyl sulfoxide (DMSO).
5. preparation method according to claim 1, is characterized in that: in step (1), and described rare gas element is argon gas or nitrogen.
6. preparation method according to claim 1, is characterized in that: in step (1), and described purifying carries out separation and purification by chromatographic column.
7. preparation method according to claim 1, is characterized in that: in step (3), and described acid binding agent is Anhydrous potassium carbonate, triethylamine or pyridine.
8. preparation method according to claim 1, is characterized in that: in step (3), and the described nucleophilic reagent that can form carbanion is nitropropane, dibromo fluorenes or diethyl malonate.
9. preparation method according to claim 1, is characterized in that: in step (3), and the mol ratio that the nucleophilic reagent of the positive butyl ester of position, gulf mono-nitration list Liu Huan perylene tetracarboxylic acid, acid binding agent and carbanion adds is 1:1-10:1-20.
10. preparation method according to claim 1, is characterized in that: in step (3), and the positive butyl ester of described every gram of mono-nitration list Liu Huan perylene tetracarboxylic acid uses solvent 10-200 milliliter.
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| CN106831816A (en) * | 2017-02-27 | 2017-06-13 | 山东师范大学 | A kind of gulf position embedding hexa-atomic thia ring and the hexa-atomic perylene tetracarboxylic acid diimides of oxa- ring 3,4,9,10 and preparation method thereof |
| CN106831816B (en) * | 2017-02-27 | 2019-02-19 | 山东师范大学 | A kind of gulf position embedding hexa-atomic thia ring and hexa-atomic oxa- ring -3,4,9,10- tetracarboxylic acid diimide and preparation method thereof |
| CN106883242A (en) * | 2017-04-11 | 2017-06-23 | 山东师范大学 | A kind of preparation method of embedding 3,4,9,10 perylene tetracarboxylic acid diimides of hexa-atomic oxa- ring diphenol generation in gulf position |
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