CN103570713A - Polymerizable perylene bisimide photoelectric acceptor material and synthetic method thereof - Google Patents

Polymerizable perylene bisimide photoelectric acceptor material and synthetic method thereof Download PDF

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CN103570713A
CN103570713A CN201210267129.XA CN201210267129A CN103570713A CN 103570713 A CN103570713 A CN 103570713A CN 201210267129 A CN201210267129 A CN 201210267129A CN 103570713 A CN103570713 A CN 103570713A
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perylene
diimide
bis
amino
ethyl hexyl
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徐清
易思利
赵佳
黄立滨
胡建栋
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Ningbo University
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract

The invention discloses a polymerizable perylene bisimide photoelectric acceptor material with a structural formula as shown in the description. The advantage is that the polymerizable perylene bisimide photoelectric acceptor material has an LUMO energy level of -3.90 eV. The perylene bisimide photoelectric acceptor material is obtained by introducing alkyloxy and a triphenylamine group with a methoxy into a perylene nucleus, and has greatly improved dissolvability (soluble in common organic solvents), which facilitates further synthesis. An alkene double bond is introduced simultaneously, and thus the material can be used as a polymerization monomer for the preparation of polymer solar cell materials. Meanwhile, the synthetic method is simple; the material is strong in practicality, and can be used as a polymerizable photoelectric acceptor material in organic solar cells.

Description

A kind of Ke Ju He perylene diimide class electrophotographic receptor material and synthetic method thereof
Technical field
The invention belongs to photoelectric material technical field.Be specifically related to a kind of Ke Ju He perylene diimide class electrophotographic receptor material and synthetic method thereof.
Background technology
Charge transfer material in solar cell is a class when having current carrier (electronics or hole) to inject, and under electric field action, can realize the controlled oriented and ordered movement of current carrier, thus the organic semiconductor material that carries out electric charge transmission.Generally according to the difference of its transmission current carrier kind, classify, can be divided into electron transport material and hole mobile material.Acceptor material as transmission electronic need to have lower lumo energy to accept electronics, needs to have good electron transport ability simultaneously.At present, the organic photoelectric acceptor material of bibliographical information mainly comprises four cyano benzoquinones bismethane (TCNQ), C60 and derivative, oxadiazole (oxadiazole) thereof, triazole (Triazole), fluoro polythiophene class, perylene diimide and derivative thereof etc.
Perylene diimide derivative has excellent thermostability, light stability, chemical stability because of its special structure, and high electron affinity and very strong electronic capability, is a kind of comparatively desirable electron acceptor material.In addition small molecules perylene diimide has the lumo energy suitable with PCBM, and the π-π of the large π key of its conjugation is stacking makes it have higher electronic mobility, and its strong absorption in visible region is simultaneously again that the general acceptors such as PCBM are incomparable.Within 2008, the Tong Guo of Mohammad K.Nazeeruddin working group loads to TiO Jiang perylene diimide 2the photovoltaic cell of upper preparation is at simulated solar irradiation (100mWcm -2, 1.5AM global) irradiation under, electricity conversion has reached 6.8%, open circuit voltage 728mV, packing factor reached 0.74 (ChemSusChem, 2008,1:615-618).
， perylene diimide is because of its good electroluminescence characters in recent years, in the application aspect of organic photoelectric functional material, gets most of the attention.And on the basis of small molecules flower imide research how by its macromolecular, become equally the focus of current research.But the large π key planar conjugate structure of You Yu perylene, makes the solvability of its small molecule material very poor, so that limited to a certain extent it, further synthesize.Therefore synthetic polymerizable perylene diimide monomer, the macromolecular of Dui Yu perylene diimide will have very important significance.
Summary of the invention
Technical problem: the object of this invention is to provide a kind of polymerizable flower acid imide electrophotographic receptor material and synthetic method thereof, olefinic double bonds is introduced in design, makes it can be used as polymerization single polymerization monomer and prepares polymer solar battery material.By by alkoxyl group and with the trianilino group Yin Ru perylene core of methoxyl group, the solvability of Gai Shan perylene diimide.
Technical scheme: Ke Ju He perylene diimide class electrophotographic receptor material structure formula of the present invention is:
Figure BSA00000757423300021
Described Ke Ju He perylene diimide class electrophotographic receptor material Tong Guo perylene diimide derivative and acrylate chloride obtain under anhydrous condition, solvent for use is methylene dichloride (adds after hydrolith is dried and heavily steam), alkali is triethylamine or pyridine, and temperature of reaction is-5-0 ℃ that the reaction times is 5-8h.
Suo Shu perylene diimide derivative is N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, by N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide is hydrolyzed and obtains under alkaline condition, solvent for use is the mixed solvent of tetrahydrofuran (THF) and ethanol, alkali is LiOH or the NaOH aqueous solution, and temperature of reaction is 20-40 ℃, reaction times 1-3h.
Described N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--(4-p-methoxy-phenyl) amino) perylene-3; 4:9; 10-tetracarboxylic acid diimide is by N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9,10-tetracarboxylic acid diimide reacts and obtains under the protection of rare gas element with 4-(two-(4-p-methoxy-phenyl) amino) phenylo boric acid.Solvent for use is toluene or DMF, and catalyzer is Pd (PPh 3) 4, alkali is K 2cO 3or Na 2cO 3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 95-105 ℃, the reaction times is 24-36h.
Described N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3,4:9,10-tetracarboxylic acid diimide is by 1; 7-bis--bromine-perylene-3; 4:9,10-tetracarboxylic anhydride reacts and obtains under the protection of rare gas element with 2-ethyl hexyl oxy propylamine and 6-amino-hexanol, and solvent for use is N; dinethylformamide or N-Methyl pyrrolidone and glacial acetic acid mixing solutions; temperature of reaction is 150 ℃, and rare gas element is nitrogen, and the reaction times is 36-60h.
Compared with prior art, the invention has the advantages that, by by alkoxyl group and with the trianilino group Yin Ru perylene core of methoxyl group, get is Dao perylene diimide class electrophotographic receptor material, and solvability has obtained very large improvement, is conducive to that it is further synthetic.Introduced olefinic double bonds simultaneously, made it can be used as polymerization single polymerization monomer and prepare polymer solar battery material.And its simple synthetic method, practical, can be used as polymerizable electrophotographic receptor material and be applied in organic solar batteries.
Accompanying drawing explanation
The synthesis path of Gai perylene diimide class electrophotographic receptor material of Fig. 1 Wei;
Fig. 2 be the prepared colored acid imide electrophotographic receptor material of embodiment 1 magnetic resonance spectroscopy ( 1hNMR) spectrogram;
Fig. 3 is the uv absorption spectra of the prepared perylene diimide of embodiment 1 class electrophotographic receptor material film;
Fig. 4 is the cyclic voltammetric collection of illustrative plates of the prepared perylene diimide class electrophotographic receptor material of embodiment 1.
Embodiment
Below by embodiment, further illustrate the synthetic of acceptor material of the present invention, rather than will limit the present invention with these examples.
Embodiment 1:
(1) take compound 1; the bromo-perylene tetracarboxylic acid acid anhydride of 7-bis-(2.20g; 4mmol) be placed in 200mL there-necked flask; measure 60mL N-Methyl pyrrolidone and 40mL glacial acetic acid adds in bottle; ultrasonic 20min under nitrogen protection, then adds respectively 2-ethyl hexyl oxy propylamine (1.32mL, 6mmol), 6-amino-hexanol (0.70g; 5.9mmol), 150 ℃ of stirring 24h under nitrogen protection.After reaction finishes, be cooled to room temperature, filter, filtrate is poured in 100mL methyl alcohol, in the refrigerator of-10 ℃, refrigerate and spend the night.Filtered and recycled red precipitate, it is dry in vacuum drying oven.Take ethyl acetate: methylene dichloride: sherwood oil=1: be at 10: 10 leacheate, with alumina column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--bromine-perylene-3,4:9,10-tetracarboxylic acid diimide, productive rate is 32%.
(2) measuring 80mL toluene (dry through hydrolith) adds in the there-necked flask of 250mL; under nitrogen protection by compound N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9; 10-tetracarboxylic acid diimide (1.0g, 1.13mmol), 4-(two-(4-p-methoxy-phenyl) amino) phenylo boric acid (0.90g; 2.57mmol), K 2cO 3the aqueous solution (2M, 18mL), Pd (PPh 3) 4(65.2mg, 0.06mmol) adds in bottle.Under nitrogen protection, 105 ℃ are stirred 24h.After end, be cooled to room temperature, add 80mL saturated aqueous common salt, stir after half an hour standingly, use separating funnel separatory.Get the anhydrous MgSO of upper strata liquid 4after dry, decompress filter is removed toluene, is placed in vacuum drying oven dry, without purifying, directly enters next step.
(3) after being dissolved with 30mL THF, (2) reacted mixture adds in tri-mouthfuls of round-bottomed flasks of 100mL, add again 20mL ethanol and LiOH solution (20mL, 2M), stir 3h at 40 ℃, after question response finishes, add 50mL saturated aqueous common salt, separatory is removed THF.Take ethyl acetate: methylene dichloride=10: 1 is leacheate, with silicagel column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, two step overall yields are 50%.
(4) by N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide (0.61g, 0.47mmol), triethylamine (0.10mL, 0.71mmol), the CH of 20mL 2cl 2(add after hydrolith is dried and heavily steam) adds in the there-necked flask of 100mL, sonic oscillation 10min, the cryosel that is placed in-5 ℃ is bathed, drip while stirring the dichloromethane solution (0.09g of acrylate chloride, 1.18mmol, 10mL), dropping process continues about 1h, at room temperature react subsequently 7h, with TLC, follow the tracks of reaction.After question response finishes, add 10mL pure water, stir half an hour, stratification.Use separating funnel separatory, get the anhydrous MgSO of subnatant 4dry, remove by filter MgSO 4, with Rotary Evaporators, be spin-dried for methylene dichloride.Take ethyl acetate: methylene dichloride=1: 10 is leacheate, with silicagel column, to purify and obtain Suo Shu perylene diimide acceptor material, productive rate is 46%.IR(KBr，cm -1)2959，2927，2842，1728，1695，1663，1590，1505，1401，1329，1270，1250，1165，1099，1041，857，831，733。
(5) nmr analysis of Suo Shu perylene diimide acceptor material is shown in Fig. 2, and result shows the multiplet of chemical shift δ 7.96-8.59 Wei perylene core, and δ 6.84-7.36 is the absorption peak of aromatic amine phenyl ring proton, and δ 3.83 is the absorption peak of methoxyl group on aromatic amine phenyl ring.
(6) uv-absorbing of Suo Shu perylene diimide acceptor material in methylene dichloride is shown in Fig. 3, and result shows that the absorption region of this acceptor material has covered whole visible region and extended to near-infrared region.
(7) Suo Shu perylene diimide acceptor material is solvent at methylene dichloride, and tetrabutylammonium perchlorate sees Fig. 4 for the cyclic voltammetric in electrolytical solution, by figure, can show that its lumo energy is-3.90eV.
Embodiment 2:
(1) take compound 1; the bromo-perylene tetracarboxylic acid acid anhydride of 7-bis-(2.20g; 4mmol) be placed in 200mL there-necked flask; measure 60mLN-methyl-2-pyrrolidone and 40mL glacial acetic acid adds in bottle; ultrasonic 20min under nitrogen protection, then adds respectively 2-ethyl hexyl oxy propylamine (1.32mL, 6mmol), 6-amino-hexanol (0.70g; 5.9mmol), 150 ℃ of stirring 60h under nitrogen protection.After reaction finishes, be cooled to room temperature, filter, filtrate is poured in 100mL methyl alcohol, in the refrigerator of-10 ℃, refrigerate and spend the night.Filtered and recycled red precipitate, it is dry in vacuum drying oven.Take ethyl acetate: methylene dichloride: sherwood oil=1: be at 10: 10 leacheate, with alumina column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--bromine-perylene-3,4:9,10-tetracarboxylic acid diimide, productive rate is 36%.
(2) measuring 80mL toluene (dry through hydrolith) adds in the there-necked flask of 250mL; under nitrogen protection by compound N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9; 10-tetracarboxylic acid diimide (1.0g, 1.13mmol), 4-(two-(4-p-methoxy-phenyl) amino) phenylo boric acid (0.90g; 2.57mmol), K 2cO 3the aqueous solution (2M, 18mL), Pd (PPh 3) 4(65.2mg, 0.06mmol) adds in bottle.Under nitrogen protection, 95 ℃ are stirred 36h.After end, be cooled to room temperature, add 80mL saturated aqueous common salt, stir after half an hour standingly, use separating funnel separatory.Get the anhydrous MgSO of upper strata liquid 4after dry, decompress filter is removed toluene, is placed in vacuum drying oven dry, without purifying, directly enters next step.
(3) after being dissolved with 30mLTHF, (2) reacted mixture adds in tri-mouthfuls of round-bottomed flasks of 100mL, add again 20mL ethanol and LiOH solution (20mL, 2M), stir 3h at 20 ℃, after question response finishes, add 50mL saturated aqueous common salt, separatory is removed THF.Take ethyl acetate: methylene dichloride=10: 1 is leacheate, with silicagel column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, two step overall yields are 42%.
(4) by N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide (0.61g, 0.47mmol), triethylamine (0.10mL, 0.71mmol), the CH of 20mL 2cl 2(add after hydrolith is dried and heavily steam) adds in the there-necked flask of 100mL, sonic oscillation 10min, the cryosel that is placed in 0 ℃ is bathed, drip while stirring the dichloromethane solution (0.09g of acrylate chloride, 1.18mmol, 10mL), dropping process continues about 1h, at room temperature react subsequently 5h, with TLC, follow the tracks of reaction.After question response finishes, add 10mL pure water, stir half an hour, stratification.Use separating funnel separatory, get the anhydrous MgSO of subnatant 4dry, remove by filter MgSO 4, with Rotary Evaporators, be spin-dried for methylene dichloride.Take ethyl acetate: methylene dichloride=1: 10 is leacheate, with silicagel column, to purify and obtain Suo Shu perylene diimide acceptor material, productive rate is 46%.Other and embodiment 1 are similar.
Embodiment 3:
(1) take compound 1; the bromo-perylene tetracarboxylic acid acid anhydride of 7-bis-(2.20g; 4mmol) be placed in 200mL there-necked flask; measure 60mLN-methyl-2-pyrrolidone and 40mL glacial acetic acid adds in bottle; ultrasonic 20min under nitrogen protection, then adds respectively 2-ethyl hexyl oxy propylamine (1.32mL, 6mmol), 6-amino-hexanol (0.70g; 5.9mmol), 150 ℃ of stirring 60h under nitrogen protection.After reaction finishes, be cooled to room temperature, filter, filtrate is poured in 100mL methyl alcohol, in the refrigerator of-10 ℃, refrigerate and spend the night.Filtered and recycled red precipitate, it is dry in vacuum drying oven.Take ethyl acetate: methylene dichloride: sherwood oil=1: be at 10: 10 leacheate, with alumina column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--bromine-perylene-3,4:9,10-tetracarboxylic acid diimide, productive rate is 28%.
(2) measuring 80mL toluene (dry through hydrolith) adds in the there-necked flask of 250mL; under nitrogen protection by compound N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9; 10-tetracarboxylic acid diimide (1.0g, 1.13mmol), 4-(two-(4-p-methoxy-phenyl) amino) phenylo boric acid (0.90g; 2.57mmol), K 2cO 3the aqueous solution (2M, 18mL), Pd (PPh 3) 4(65.2mg, 0.06mmol) adds in bottle.Under nitrogen protection, 95 ℃ are stirred 24h.After end, be cooled to room temperature, add 80mL saturated aqueous common salt, stir after half an hour standingly, use separating funnel separatory.Get the anhydrous MgSO of upper strata liquid 4after dry, decompress filter is removed toluene, is placed in vacuum drying oven dry, without purifying, directly enters next step.
(3) after being dissolved with 30mLTHF, (2) reacted mixture adds in tri-mouthfuls of round-bottomed flasks of 100mL, add again 20mL ethanol and LiOH solution (20mL, 2M), stir 1h at 20 ℃, after question response finishes, add 50mL saturated aqueous common salt, separatory is removed THF.Take ethyl acetate: methylene dichloride=10: 1 is leacheate, with silicagel column, purify to be dried and obtain product N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, two step overall yields are 39%.
(4) by N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide (0.61g, 0.47mmol), triethylamine (0.10mL, 0.71mmol), the CH of 20mL 2cl 2(add after hydrolith is dried and heavily steam) adds in the there-necked flask of 100mL, sonic oscillation 10min, the cryosel that is placed in-5 ℃ is bathed, drip while stirring the dichloromethane solution (0.09g of acrylate chloride, 1.18mmol, 10mL), dropping process continues about 1h, at room temperature react subsequently 4h, with TLC, follow the tracks of reaction.After question response finishes, add 10mL pure water, stir half an hour, stratification.Use separating funnel separatory, get the anhydrous MgSO of subnatant 4dry, remove by filter MgSO 4, with Rotary Evaporators, be spin-dried for methylene dichloride.Take ethyl acetate: methylene dichloride=1: 10 is leacheate, with silicagel column, to purify and obtain Suo Shu perylene diimide acceptor material, productive rate is 40%.Other and embodiment 1 are similar.
Embodiment 4:
Other are with embodiment 1, synthetic N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--bromine-perylene-3,4:9,10-tetracarboxylic acid diimide, solvent for use is N, the mixed solvent of dinethylformamide and glacial acetic acid, reaction times is 60h, and other and embodiment 1 are that similarly productive rate is 38%.
Embodiment 5:
Other are with embodiment 1, and synthetic N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, DMF used, alkali is Na 2cO 3the aqueous solution, reaction times is 36h, synthetic N-(3-(2-ethyl hexyl oxy)-N-hexanol-1,7-bis--(4-p-methoxy-phenyl) amino) perylene-3,4:9,10-tetracarboxylic acid diimide, alkali is the NaOH aqueous solution, other and embodiment 1 are that similarly the productive rate of two-step reaction is 46%.
Embodiment 6:
Other synthesize described Ke soluble perylene diimide electrophotographic receptor material with embodiment 1, and alkali used is pyridine, and other and embodiment 1 are that similarly productive rate is 56%.

Claims (5)

1. can gather and close a perylene diimide class electrophotographic receptor material, structural formula is:
Figure FSA00000757423200011
2. one kind can be gathered the synthetic method of closing perylene diimide class electrophotographic receptor material, it is characterized in that: described a kind of Ke Ju He perylene diimide class electrophotographic receptor material Tong Guo perylene diimide derivative and acrylate chloride obtain under anhydrous condition, solvent for use is methylene dichloride (adds after hydrolith is dried and heavily steam), alkali is triethylamine or pyridine, temperature of reaction is-5-0 ℃ that the reaction times is 4-6h.
3. the synthetic method of a kind of Ke dissolubility Ju He perylene diimide class electrophotographic receptor material according to claim 2, it is characterized in that: perylene diimide derivative is N-(3-(2-ethyl hexyl oxy)-N-hexanol-1, 7-bis--(4-p-methoxy-phenyl) amino) perylene-3, 4:9, 10-tetracarboxylic acid diimide is by N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1, 7-bis--(4-p-methoxy-phenyl) amino) perylene-3, 4:9, 10-tetracarboxylic acid diimide is hydrolyzed and obtains under alkaline condition, solvent for use is the mixed solvent of tetrahydrofuran (THF) and ethanol, alkali is LiOH or the NaOH aqueous solution, temperature of reaction is 20-40 ℃, reaction times 1-3h.
4. the synthetic method of a kind of Ke Ju He perylene diimide class electrophotographic receptor material according to claim 3; it is characterized in that: N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--(4-p-methoxy-phenyl) amino) perylene-3; 4:9; 10-tetracarboxylic acid diimide is by N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9,10-tetracarboxylic acid diimide reacts and obtains under the protection of rare gas element with 4-(two-(4-p-methoxy-phenyl) amino) phenylo boric acid.Solvent for use is toluene or DMF, and catalyzer is Pd (PPh 3) 4, alkali is K 2cO 3or Na 2cO 3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 95-105 ℃, the reaction times is 24-36h.
5. the synthetic method of a kind of Ke Ju He perylene diimide class electrophotographic receptor material according to claim 4; it is characterized in that: N-(3-(2-ethyl hexyl oxy)-N-hexyl acetate-1; 7-bis--bromine-perylene-3; 4:9; 10-tetracarboxylic acid diimide is by 1; 7-bis--bromine-perylene-3; 4:9; 10-tetracarboxylic anhydride reacts and obtains under the protection of rare gas element with 2-ethyl hexyl oxy propylamine and 6-amino-hexanol; solvent for use is DMF or N-Methyl pyrrolidone and glacial acetic acid mixing solutions; temperature of reaction is 150 ℃, and rare gas element is nitrogen, and the reaction times is 36-60h.
CN201210267129.XA 2012-07-20 2012-07-20 Polymerizable perylene bisimide photoelectric acceptor material and synthetic method thereof Pending CN103570713A (en)

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CN107964021A (en) * 2017-11-30 2018-04-27 华南理工大学 A kind of acid imide photoelectricity small molecule material of boracic nitrogen key and preparation method and application
CN108847357A (en) * 2018-06-28 2018-11-20 中国海洋大学 Modified acid imide/the polyaniline composite electrode material of NaOH and its volumetric properties
CN111057174A (en) * 2019-12-30 2020-04-24 常熟涤纶有限公司 Polystyrene high-fluorescence microsphere and preparation method thereof

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CN106916154A (en) * 2017-03-16 2017-07-04 南京邮电大学 A kind of size adjustable perylene diimide class multifunctional nanoparticles and its preparation and application
CN107964021A (en) * 2017-11-30 2018-04-27 华南理工大学 A kind of acid imide photoelectricity small molecule material of boracic nitrogen key and preparation method and application
CN108847357A (en) * 2018-06-28 2018-11-20 中国海洋大学 Modified acid imide/the polyaniline composite electrode material of NaOH and its volumetric properties
CN111057174A (en) * 2019-12-30 2020-04-24 常熟涤纶有限公司 Polystyrene high-fluorescence microsphere and preparation method thereof
CN111057174B (en) * 2019-12-30 2022-03-25 常熟涤纶有限公司 Polystyrene high-fluorescence microsphere and preparation method thereof

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