CN103242312B - A kind of efficient method preparing Bing bis-perylene diimides derivative - Google Patents
A kind of efficient method preparing Bing bis-perylene diimides derivative Download PDFInfo
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Abstract
The invention discloses a kind of novel method of efficient preparation Bing bis-perylene diimides derivative.The general structure of this compound is such as formula shown in I.Its preparation method comprises the steps: in an inert atmosphere, the compound shown in formula II, copper catalyst, organic micromolecule ligand and organic bases is reacted, obtains compound shown in formula I.Synthetic route provided by the invention has simply efficiently, environmental pollution is little, cheaper starting materials, synthesis cost are low, have the advantages such as fine universality and repeatability, can promote the use of the synthesis of other various N substituent Bing bis-perylene diimides derivative.
Description
Technical field
The present invention relates to a kind of method preparing Bing bis-perylene diimides derivative.
Background technology
Perylene diimides derivative is the common commercial pigments of a class, is widely used in the industrial circle such as dyestuff, coating.Be endowed new performance and application along with Materials science constantly develops ， perylene diimides derivative, its photoelectric properties highlight day by day, so have consequence and application prospect in organic photoelectrical material field.Such as, organic semiconductor field, includes field effect transistors, Organic Light Emitting Diode and organic photovoltaic material etc., wherein particularly organic field effect tube material, due to the semiconducting behavior of its excellence, causes the concern of semi-conductor industry circle.Researchist, by different synthetic methods, has prepared Yi Xi Lie perylene diimides derivative, has developed the organic semiconductor material of a large amount of superior performance.
But, up to now, synthesis the method for two perylene diimides precursor skeletons is but very limited, patent of its application also just following several: CN101423522, WO2010111822 and WO2010112452.
Based on reporting patent, the synthesis of known Bing bis-perylene diimides precursor skeleton not easily: methodology of organic synthesis is extremely limited, so far untapped go out efficient synthetic route; Reaction yield is very low, usually below 15%, is unfavorable for industry's enlarging production; Severe reaction conditions, high to reaction mass purity requirement, very responsive to oxygen G&W, poor repeatability; Reaction times is of a specified duration, and the production cycle is long, can not meet High-efficient Production; Reaction raw materials remains in a large number, and by product is various in addition, and pole is unfavorable for abstraction and purification, easily because aftertreatment brings a large amount of environmental pollutions and material loss.
In sum, the source of Bing bis-perylene diimides parent compound is a bottleneck step that can not cross over for it in the application of Material Field.Therefore, the new synthesis process that development is green, improves its productive rate and purity, shortening production cycle, reduces energy consumption, decreasing pollution thing discharges, and is that material prepares the first step had to pass through, for new diseases provides basic guarantee.
Summary of the invention
Technical problem to be solved by this invention is to overcome the weak point that Bing bis-perylene diimides derivative preparation method in prior art exists, and develops a kind of simple process, favorable reproducibility and the higher method preparing Bing bis-perylene diimides derivative of productive rate efficiency.
The general structure of Bing bis-perylene diimides derivative of the present invention is such as formula shown in I:
(formula I)
In formula I, described R is selected from hydrogen, C
4-C
25any one in the aryl of alkyl and replacement; Substituting group in the aryl of described replacement is C
2-C
12alkyl; Described X is Cl or Br.
Abovementioned alkyl comprises the alkyl of straight chain and side chain.
The method of the perylene diimides of Bing bis-shown in preparation formula I provided by the present invention derivative, comprise the steps: in an inert atmosphere, four Lu Dai perylene diimides derivatives, copper catalyst, organic micromolecule ligand and organic bases shown in formula II are reacted, obtains the bis-of Bing shown in formula I perylene diimides derivative.
(formula II)
In formula II, the definition cotype I of R, X.
In aforesaid method, described copper catalyst is selected from following at least one: cuprous iodide, cuprous bromide, cuprous chloride and trifluoromethanesulfonic acid are cuprous; Be wherein catalyzer with cuprous iodide, productive rate is best.
In aforesaid method, described organic micromolecule ligand is selected from following at least one: pyridine-2-formic acid, pyridine-2-sodium formiate, pyridine-2-potassium formiate, thiophene-2-carboxylic acid, thiophene-2-carboxylic acid sodium and thiophene-2-carboxylic acid potassium; Wherein with thiophene-2-carboxylic acid potassium for part, productive rate is best.
In aforesaid method, described organic bases is selected from least one in sodium ethylate, sodium acetate, Sodium Propionate, trimethylacetic acid sodium, potassium ethylate, trimethyl carbinol lithium, sodium tert-butoxide, potassium tert.-butoxide, potassium acetate, potassium propionate and trimethylacetic acid potassium; Be wherein alkali with potassium tert.-butoxide, productive rate is best.
React described in aforesaid method and carry out in organic solvent, the mixed solvent of described organic solvent dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-dimethylacetamide, N-Methyl pyrrolidone or these solvents; Wherein with dimethyl sulfoxide (DMSO) or tetramethylene sulfone for solvent, productive rate is best.Solvent is domestic chemical pure rank, without the need to the drying that strictly dewaters before reaction.
Described inert atmosphere is nitrogen atmosphere or argon gas atmosphere.
In aforesaid method, the molar ratio of four Lu Dai perylene diimides derivatives shown in described starting materials of formulae II, copper catalyst, organic micromolecule ligand, organic bases is followed successively by 1: 1-10: 1-10: 1-10, and preferably 1: 2.5: 2.5: 2.5.
In aforesaid method, the temperature of reaction of described reaction is 70-120 DEG C, preferred 70-90 DEG C, and the reaction times is 8-15 hour, preferred 10-12 hour.Optimum reaction condition was: 90 DEG C of reactions 12 hours.
The present invention relates to raw material four halogen and under copper catalyst (as cuprous iodide) and organic micromolecule ligand (as thiophene-2-carboxylic acid potassium) effect, bimolecular linked reaction occurs for perylene diimides derivative (if four chlorine are for perylene diimides), and be organic bases with potassium tert.-butoxide, one step efficiently builds the copline dimer by three singly-bound bridgings, and productive rate is up to 56%.Reaction in the present invention is all not harsh, easy and simple to handle to raw material, reagent and condition, and abstraction and purification is easy.
The invention has the advantages that:
1, this serial reaction route has simply efficient, that environmental friendliness, cost of material are cheap, reagent dosage reduces advantage; To raw materials used, reagent and solvent requirement not high, chemical pure; Operation is without the need to strict anhydrous and oxygen-free method; Universality is high, reproducible, and productive rate is high; And expand the range of choice of catalyzer and part, therefore, efficiently avoid the defect of patent CN101423522, WO2010111822 and WO2010112452.
2, the different alkyl that replaces or aromatic group can make the physicals variation of Bing bis-perylene diimides and derivative thereof, and such as long alkyl group has certain liquid crystal property, extends its range of application.
3, for organic semiconductor field-effect material provides a kind of basic raw material be easy to get.
Accompanying drawing explanation
Fig. 1 is the optimum synthetic route chart that the present invention prepares Bing bis-perylene diimides derivative method.
Fig. 2 is the single crystal structure figure of C4-4CldiPBI prepared by embodiment 1.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.
Described in following embodiment, method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.
Embodiment 1, preparation C4-4CldiPBI (2a) (R=C in formula I
4h
9, X=Cl compound)
In 100mL two mouthfuls of round-bottomed flasks, vacuumize logical argon gas.Then Si Lv perylene diimides raw material (1a) (R=C in formula II is added
4h
9, X=Cl compound) (1.28g, 2.0mmol), cuprous iodide (0.95g, 5.0mmol), thiophene-2-carboxylic acid potassium (0.83g, 5.0mmol), potassium tert.-butoxide (0.56g, 5.0mmol).At room temperature inject dimethyl sulfoxide (DMSO) (40mL), 90 DEG C are stirred 12h.Stop heating, naturally cooling, pours into reaction mixture in 200mL deionized water, fully stirs.With the above-mentioned mixing solutions of filtered on buchner funnel, filter cake 100mL saturated ammonia water washing, removes a large amount of cupric ion.300mL deionized water wash used again by filter cake, and 100mL anhydrous methanol washs, and dries at 100 DEG C.Finally, filter cake is dissolved in 100mL methylene dichloride, mixes sample make dry powder with diatomite, then by chromatographic column (leacheate is sherwood oil: methylene dichloride=1: 2 volume ratios), obtains atropurpureus solid 0.48g (productive rate: 43%).
The structure confirmation data of this product is as follows:
Mass spectrum: MS (MALDI-TOF): cacld for M
-, 1134.2; Found, 1134.2.
Nucleus magnetic hydrogen spectrum:
1h NMR (400MHz, CDCl
3) δ (ppm): δ=10.04 (s, 2H, perylene-H), 9.24 (s, 2H, perylene-H), 8.99 (s, 2H, perylene-H), 4.42 (t, 4H, alkyl-H), 4.30 (t, 4H, alkyl-H), (1.98-1.90 m, 4H, alkyl-H), (1.84-1.80 m, 4H, alkyl-H), 1.61-1.51 (m, 8H, alkyl-H), 1.09-1.00 (m, 12H, methyl-H).
Nuclear-magnetism carbon is composed:
13c NMR (101MHz, CDCl
3) δ (ppm): δ=164.4,163.5,162.9,162.6,136.2,136.1,135.5,134.1,132.4,131.1,130.2,129.1,127.2,126.3,125.9,124.8,124.6,124.3,123.8,122.2,121.2,119.3,41.9,41.1,30.6,30.5,20.8,20.6,14.1,14.0.
Single crystal structure is shown in Fig. 2.As from the foregoing, this compound structure is correct, is target compound C4-4CldiPBI (2a).
Embodiment 2, preparation C4-4CldiPBI (2a)
Preparation method is substantially with embodiment 1, and difference is: 90 in embodiment 1 DEG C are stirred 12h and replace with 70 DEG C of stirring 15h, obtain atropurpureus solid 0.43g (productive rate: 38%).
Embodiment 3, preparation C4-4CldiPBI (2a)
Preparation method is substantially with embodiment 1, and difference is: 90 in embodiment 1 DEG C are stirred 12h and replace with 120 DEG C of stirring 8h, obtain atropurpureus solid 0.35g (productive rate: 31%).
Embodiment 4, preparation C4-4CldiPBI (2a)
Preparation method is substantially with embodiment 1, and difference is: the cuprous iodide (0.95g, 5.0mmol) in embodiment 1 is replaced with cuprous chloride (0.49g, 5.0mmol).90 DEG C are stirred 12h and replace with 120 DEG C of stirring 8h, obtain atropurpureus solid 0.33g (productive rate: 29%).
Embodiment 5, preparation C4-4CldiPBI (2a)
Preparation method is substantially with embodiment 1, and difference is: the thiophene-2-carboxylic acid potassium (0.83g, 5.0mmol) in embodiment 1 is replaced with pyridine-2-potassium formiate (0.80g, 5.0mmol).Obtain atropurpureus solid 0.29g (productive rate: 26%).
Embodiment 6, preparation Cl2-4CldiPBI (2b) (R=C in formula I
12h
25, X=Cl compound)
In 100mL two mouthfuls of round-bottomed flasks, vacuumize logical argon gas.Then Si Lv perylene diimides raw material (1b) (R=C in formula II is added
12h
25, X=Cl compound) (1.73g, 2.0mmol), cuprous iodide (0.95g, 5.0mmol), thiophene-2-carboxylic acid potassium (0.83g, 5.0mmol) and potassium tert.-butoxide (0.56g, 5.0mmol).At room temperature inject dimethyl sulfoxide (DMSO) (40mL), 90 DEG C are stirred 12h.Stop heating, naturally cooling, pours into reaction mixture in 200mL deionized water, fully stirs.With the above-mentioned mixing solutions of filtered on buchner funnel, filter cake 100mL saturated ammonia water washing, removes a large amount of cupric ion.300mL deionized water wash used again by filter cake, and 100mL anhydrous methanol washs, and dries at 100 DEG C.Finally, filter cake is dissolved in 100mL methylene dichloride, mixes sample make dry powder with diatomite, then by chromatographic column (leacheate is sherwood oil: methylene dichloride=1: 1 volume ratio), obtains atropurpureus solid 0.82g (productive rate: 52%).
The structure confirmation data of this product is as follows:
Mass spectrum: MS (MALDI-TOF): cacld for M-, 1582.7; Found, 1582.9.
Nucleus magnetic hydrogen spectrum:
1h NMR (400MHz, CDCl
3) δ (ppm): 10.05 (s, perylene-H, 2H), 9.25 (s, perylene-H, 2H), 9.00 (s, perylene-H, 2H), 4.41 (t, alkyl-H, 4H), 4.29 (t, alkyl-H, 4H), 2.02-1.89 (m, alkyl-H, 8H), 1.49-1.25 (m, alkyl-H, 60H), 0.88-0.83 (m, alkyl-H, 12H).
Nuclear-magnetism carbon is composed:
13c NMR (101MHz, CDCl
3) δ (ppm): 164.3,163.4,162.8,162.5,136.2,136.1,135.4,134.0,132.3,131.0,130.0,129.0,127.1,126.2,125.8,124.6,124.5,124.2,123.7,122.1,119.2,42.1,41.3,32.1,29.9,29.8,29.7,29.6,29.5,28.4,28.3,27.4,22.8,14.2.
As from the foregoing, this compound structure is correct, is target compound C12-4CldiPBI (2b).
Embodiment 7, preparation C12-4CldiPBI (2b)
Preparation method is substantially with embodiment 6, and difference is: 90 in embodiment 6 DEG C are stirred 12h and replace with 70 DEG C of stirring 15h, obtain atropurpureus solid 0.69g (productive rate: 44%).
Embodiment 8, preparation C12-4CldiPBI (2b)
Preparation method is substantially with embodiment 6, and difference is: 90 in embodiment 6 DEG C are stirred 12h and replace with 120 DEG C of stirring 8h, obtain atropurpureus solid 0.62g (productive rate: 39%).
Embodiment 9, preparation C12-4CldiPBI (2b)
Preparation method is substantially with embodiment 6, and difference is: the cuprous iodide (0.95g, 5.0mmol) in embodiment 6 is replaced with cuprous chloride (0.49g, 5.0mmol).90 DEG C are stirred 12h and replace with 120 DEG C of stirring 8h, obtain atropurpureus solid 0.47g (productive rate: 30%).
Embodiment 10, preparation C12-4CldiPBI (2b)
Preparation method is substantially with embodiment 6, and difference is: the thiophene-2-carboxylic acid potassium (0.83g, 5.0mmol) in embodiment 6 is replaced with pyridine-2-potassium formiate (0.80g, 5.0mmol).Obtain atropurpureus solid 0.49g (productive rate: 31%).
Claims (9)
1. a method for compound shown in preparation formula I, comprises the steps: in an inert atmosphere, the compound shown in formula II, copper catalyst, organic micromolecule ligand and organic bases is reacted, obtains compound shown in formula I;
In formula I, described R is selected from hydrogen, C
4-C
25any one in the aryl of alkyl and replacement; Substituting group in the aryl of described replacement is C
2-C
12alkyl; Described X is Cl or Br;
In formula II, the definition cotype I of described R, X;
Described copper catalyst is selected from following at least one: cuprous iodide, cuprous bromide, cuprous chloride and trifluoromethanesulfonic acid are cuprous;
Described organic micromolecule ligand is thiophene-2-carboxylic acid potassium;
Described organic bases is selected from least one in trimethyl carbinol lithium, sodium tert-butoxide and potassium tert.-butoxide.
2. method according to claim 1, is characterized in that: described copper catalyst is cuprous iodide.
3. method according to claim 1, is characterized in that: described reaction is carried out in organic solvent, and described organic solvent is selected from following at least one: dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-dimethylacetamide and N-Methyl pyrrolidone.
4. method according to claim 3, is characterized in that: described organic solvent is selected from dimethyl sulfoxide (DMSO) and/or tetramethylene sulfone.
5. method according to claim 1, is characterized in that: shown in described formula II, the molar ratio of compound, copper catalyst, organic micromolecule ligand, organic bases is followed successively by 1:1-10:1-10:1-10.
6. method according to claim 5, is characterized in that: shown in described formula II, the molar ratio of compound, copper catalyst, organic micromolecule ligand, organic bases is followed successively by 1:2.5:2.5:2.5.
7. method according to claim 1, is characterized in that: the temperature of reaction of described reaction is 70-120 DEG C, and the reaction times is 8-15 hour.
8. method according to claim 7, is characterized in that: the temperature of reaction of described reaction is 70-90 DEG C, and the reaction times is 10-12 hour.
9. method according to claim 1, is characterized in that: described inert atmosphere is nitrogen atmosphere or argon gas atmosphere.
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| CN103819482B (en) * | 2014-03-10 | 2016-05-04 | 山东师范大学 | A kind of cyclopentadiene bridging bis-perylene diimides compound and preparation method thereof |
| US10566539B2 (en) | 2014-05-05 | 2020-02-18 | The Trustees Of Columbia University In The City Of New York | Organic semiconductor compounds and methods of use |
| CN106866671B (en) * | 2015-12-11 | 2019-02-22 | 中国科学院化学研究所 | A kind of gear type trimerization imide compound and its preparation method and application |
| CN108424413B (en) * | 2017-02-15 | 2019-09-03 | 中国科学院化学研究所 | A kind of synthesis of imide analog compounds and its preparation method and application based on three dish alkene |
| CN108503638B (en) * | 2018-04-25 | 2019-11-26 | 福建师范大学福清分校 | A kind of method of cobalt catalysis polyhalo imidodicarbonic diamide Dehalogenation reduction |
| CN108822107B (en) * | 2018-06-08 | 2020-07-31 | 福建师范大学福清分校 | Method for dehalogenation and reduction of polyhalogenated perylene diimide aromatic hydrocarbon by nickel catalysis |
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