CN101665492A - 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof - Google Patents
1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof Download PDFInfo
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- CN101665492A CN101665492A CN200910306929A CN200910306929A CN101665492A CN 101665492 A CN101665492 A CN 101665492A CN 200910306929 A CN200910306929 A CN 200910306929A CN 200910306929 A CN200910306929 A CN 200910306929A CN 101665492 A CN101665492 A CN 101665492A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Abstract
The invention relates to a 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and a preparation method thereof, belonging to the field of organic photoelectronic functional material preparation. The structural characteristic of the perylene bisimide derivant is that 1, 6, 7, 12-four harbor positions of 3, 4, 9, 10-perylene bisimide are connected with charge transport functional groups with different structure types and different conjugation degrees by phenyls. The derivant is synthesized by the following steps: firstly, a perylene bisimide core with terminal ethyne or halogen or other active groups at the periphery is synthesized by 1, 6, 7, 12-tetraphenyl perylene; and then the 1, 6, 7, 12-tetraphenyl perylene bisimide and cyclopentadienyl ketone with functional substitute group at periphery or arylamine and the like generate Diels-Alder cycloaddtion or C-N, C-C coupling reaction and the like, thus obtaining the target derivant. The compound has excellent thermal stability and morphologic stability and dissolvability; the opto-electronic property of the compound has obvious bathochromic shift compared with other perylene bisimide derivants; and the derivant can be widely applied in the fields of photoelectron and biology such as organic electroluminescence, solar cell, near-infrared fluorescence probe and the like.
Description
Technical field
The present invention relates to the class 1,6,7 in the organic photoelectric functional material field, 12-Si Ben Ji perylene double imide derivative and preparation method thereof.
Background technology
Since Friedlander (German Patent 1913 since synthesizing perylene double imide compounds in 1913,276,956) perylene double imide dyestuff is with its superior dyeing behavior, stability and light fastness, be widely used in dyestuff and coatings industry, because its excellent planarity, advantages of higher stability and unique photoelectric properties, receive much concern in the synthetic field of the design of functional materials in recent years, as at solar cell, organic field-effect tube, electroluminescent material, the research report Showed Very Brisk (Angew.Chem. in field such as liquid crystal material and biological fluorescent labeling, Int.Ed.2004,43,6363.; J.Am.Chem.Soc.2003,125; J.Am.Chem.Soc.2003,125,437.; J.Org.Chem.2005,3715.; ).Therefore, extensively and in depth Yan Jiu perylene double imide compounds has important practical value.
Up to now, adopt two kinds of method Dui perylene double imides to carry out structural modification usually and obtain Xin De perylene double imide compounds: the one, introduce different groups in its imide position, but little at the substituting group of this position to the photoelectric property change of compound; The one, the position, four bays of Dui perylene double imide is modified, and introduces the character of the group ， Dui perylene double imide of electrophilic or power supply by position, bay halo De perylene double imide and improves bigger.A lot of significant work have been done for a kind of method in back researcher both domestic and external, but be to generate phenoxy group by halo De perylene double imide and phenols generation nucleophilic substitution to replace De perylene double imide mostly, and then group (Chem.Commun.2004,1564. of introducing other; Chem.Eur.J.2004,10,528-537), and directly introduce four other group such as phenyl, then rarely have report.This study group of primary track in 2006 successfully directly draws four phenyl into the position, bay to the perylene double imide by the Suzuki reaction, obtained absorption and transmitting boundary all broad 1,6,7,12-Si Ben Ji perylene double imide compound (Org.Lett., Vol.8, No.5,2006).About 1,6,7,12-Si Ben Ji perylene double imide derivative and preparation method thereof yet there are no report but up to now.
Summary of the invention
The objective of the invention is to introduce the group of different carrier transport functions on the 12-Si Ben Ji perylene double imide parent, to obtain having the organic photoelectric functional material of premium properties by 1,6,7.
Technical scheme of the present invention is: at first by 1,6,7, the synthetic periphery of 12-Si Ben Ji perylene double imide has end acetylene or halogen isoreactivity group De perylene double imide nuclear, and then have reactions such as generation Diels-Alder cycloaddition such as substituent cyclopentadienone of function or arylamine or C-N, C-C coupling with the periphery and make a class 1,6,7,12-Si Ben Ji perylene double imide derivative.General structure is as follows:
Wherein: R is selected from carbazyl, and 3,6-di-t-butyl carbazyl, 3,6-two (3,6-di-t-butyl carbazyl) carbazyl, naphthyl, anthryl, phenanthryl, pyrenyl, N-phenyl-1-naphthylamine base, thienyl, pyrazinyl, diazosulfide base or the following group of general structure:
R
1～R
4All be pentafluorophenyl group or R
1=R
4=phenyl, R
2=R
3The phenyl that=R base except that A, B replaces.
R '=C
8-C
12Straight chain, branched-chain alkyl or perfluoroalkyl, the general structure of perfluoroalkyl is CF
3(CF
2)
nCF
2, the even number of n=2～10.
A described class 1,6,7, the preparation method of 12-Si Ben Ji perylene double imide derivative realizes by following concrete steps:
(1) with 1,6,7, the 12-tetraphenyl replaces De perylene double imide and mixes at 1: 2.5: 2 with mol ratio with two (trifluoroacetic acid) iodobenzene, iodine, and room temperature reaction 8h in tetracol phenixin gets 1,6,7, and four pairs of iodophenyls of 12-replace De perylene double imide;
(2) with the product of trimethylsilyl acetylene and step (1), with [PdCl
2(PPh
3)
2], cuprous iodide and triphenyl phosphorus 4.8: 1: 0.2 in molar ratio: mix at 0.5: 0.5, in volume ratio is 2～3: 1 triethylamine and tetrahydrofuran solution, nitrogen protection is reacted 5～24h down for 25～40 ℃, generate 1,6,7,12-four is to (trimethylsilyl acetylene base) Ben Ji perylene double imide, be that room temperature reaction 2～6h sloughs protecting group and gets the peripheral perylene double imide that has four ethynyl active groups under 50: 1 the Neutral ammonium fluoride and the effect of tetra-n-butyl Neutral ammonium fluoride with after product in mol ratio;
(3) with two Propiophenones and 4,4 '-dibromo benzil is in ethanol solution, back flow reaction half an hour under the potassium hydroxide effect, obtain the cyclopentadienone of two bromos, then with itself and 3,6-di-t-butyl carbazole or N-phenyl-1-naphthylamine, copper powder or cuprous iodide, 18-hat-6, Anhydrous potassium carbonate 1: 3: 2 in molar ratio: mix at 0.2: 6, under the nitrogen protection, 150～200 ℃ of reaction 5～72h obtain containing the cyclopentadienone of different substituents in oil of mirbane;
(4) with the product and 3 of step (1), 6-di-t-butyl carbazole or N-phenyl-1-naphthylamine etc., cuprous iodide, 18-hat-6, Anhydrous potassium carbonate 1: 6: 4 in molar ratio: mix at 0.4: 12, in oil of mirbane, react 5～35h under the nitrogen protection and obtain corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative; Or the product of step (1) and naphthalene boronic acids, thienyl boric acid or diazosulfide boric acid are obtained by the Suzuki reaction corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative; Or the product of step (2) mixed with the product 1: 4.8 in molar ratio～12 of step (3), in o-Xylol, 160～170 ℃ of reactions 1～3 day down, obtain corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative.
De perylene double imide derivative of the present invention has advantages such as good solubility, photo and thermal stability and morphological stability and long wavelength's uv-absorbing and fluorescent emission, can be used as solar cell material, near infrared fluorescent probe material, liquid crystal material, luminescent material etc.
Embodiment
The present invention is further elaborated below by example, and purpose is better to understand content of the present invention.Therefore give an actual example and do not limit protection scope of the present invention.
The preparation of embodiment 1 compound 6
In the 100ml two-mouth bottle, add 1g (1mmol) 1,1g (2.5mmol) two (trifluoroacetic acid) iodobenzenes and 252mg iodine, room temperature reaction 3h in tetracol phenixin, column chromatography for separation gets 2 (840mg, productive rates 60%).MS：m/z：1422([M]
+)。
In the 50ml two-mouth bottle, add 1.0g (0.7mmol) intermediate 2,59mg (0.084mmol) [PdCl2 (PPh3) 2], 66.7mg (0.35mmol) CuI and 91.8mg (0.35mmol) PPh
3Add 20ml triethylamine and 10ml THF then; add trimethylsilyl acetylene 0.45ml under nitrogen protection, stirring at normal temperature 24h pours in the methylene dichloride then; filter; column chromatography for separation obtains pure product, then this pure product 800mg (0.63mmol) is mixed room temperature reaction 3h in tetrahydrofuran solution with 186.5mg (5.04mmol) Neutral ammonium fluoride and 24.7mg (0.09mmol) n-butyl ammonium fluoride; column chromatography for separation gets 3 (543mg, productive rates 85%).MS：m/z：1014([M]
+)。
In the 50ml two-mouth bottle, add 200mg (0.369mmol) 4; 178mg (0.811mmol) N-phenyl-1-naphthylamine; 118mg (1.84mmol) copper powder; 24.4mg (0.09mmol) the 18-hat-6,357mg (2.58mmol) salt of wormwood and 5ml oil of mirbane, and the nitrogen protection reflux state is reaction 72h down; removal of solvent under reduced pressure; column chromatography for separation gets 5 (257mg,, productive rate 85%).MS：m/z：：819([M+H]
+)。
Under 5 nitrogen protections of the intermediate 3 of 500mg (0.49mmol) and 2.42g (3mmol) in o-Xylol 165 ℃ the reaction 72h.Be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get target compound 1.6g (80%).MS(MALDI-TOF)：m/z：4178.([M+H]
+)。
The preparation of embodiment 2 compounds 8
Under 7 nitrogen protections of the intermediate 3 of 500mg (0.49mmol) and 2.76g (3mmol) in o-Xylol 160 ℃ the reaction 50h.Be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get target compound 1.94g (85%) MS (MALDI-TOF): m/z:4657.5 ([M+H]
+).
The preparation of embodiment 3 compounds 10
Under 9 nitrogen protections of the intermediate 3 of 100mg (0.1mmol) and 446.4mg (0.6mmol) in o-Xylol 170 ℃ the reaction 48h.Be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get target compound 271.5mg (70%).MS(MALDI-TOF)：m/z：3879([M+H]
+)。
The preparation of embodiment 4 compounds 11
In the 50ml two-mouth bottle, add 100mg (0.07mmol) intermediate 2; 117mg (0.42mmol) 3; 6-di-t-butyl carbazole; 4.8mg (0.025mmol) cuprous iodide; 16mg (0.06mmol) 18-hat-6; 115.9mg (0.84mmol) Anhydrous potassium carbonate and 5ml oil of mirbane, the following 190 ℃ of reaction 8h of nitrogen protection.Cool to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 11 (115mg, productive rates 85%).MS(MALDI-TOF)：2028([M+H]
+)。
The preparation of embodiment 5 compounds 13
The intermediate 2 that in the 50ml two-mouth bottle, adds 100mg (0.06mmol); 273.5mg (0.38mmol) 12,4.8mg (0.025mmol) cuprous iodide, 16mg (0.06mmol) 18-hat-6; 115.9mg (0.84mmol) Anhydrous potassium carbonate and 5ml oil of mirbane, the following 180 ℃ of reaction 24h of nitrogen protection.Cool to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 13 (190mg, productive rates 80%).MS(MALDI-TOF)：m/z：3890([M+H]
+)。
The preparation of embodiment 6 compounds 15
Add 100mg (0.038mmol) intermediate 14 and 325mg (0.45mmol) 9 in the 50ml two-mouth bottle, refluxed 3 days in o-Xylol under the nitrogen protection, be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 15 (260mg, productive rates 80%).MS(MALDI-TOF)：m/z：8539([M+H]
+)。
The preparation of embodiment 7 compounds 16
Add 100mg (0.038mmol) intermediate 14 and 351mg (0.45mmol) 5 in the 50ml two-mouth bottle, refluxed 3 days in o-Xylol under the nitrogen protection, be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 16 (277.5mg, productive rates 85%).MS(MALDI-TOF)：m/z：8958。
The preparation of embodiment 8 compounds 17
Add 100mg (0.038mmol) intermediate 14 and 405.4mg (0.45mmol) 7 in the 50ml two-mouth bottle, refluxed three days in o-Xylol under the nitrogen protection, be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 17 (306mg, productive rates 85%).MS(MALDI-TOF)：m/z：9920([M+H]
+)。
The preparation of embodiment 9 compounds 19
Add 200mg (0.14mmol) intermediate 18 and 790mg (0.84mmol) 7 in the 50ml two-mouth bottle, refluxed four days in o-Xylol under the nitrogen protection, be cooled to room temperature then, removal of solvent under reduced pressure, column chromatography for separation get 19 (621mg, productive rates 85%).MS(MALDI-TOF)：m/z：4431([M+H]
+)。
The preparation of embodiment 10 compounds 20
In the 50ml two-mouth bottle, add 500mg (0.35mmol) intermediate 2 and 362mg (2.1mmol) 2-naphthalene boronic acids; 658mg (7mmol) yellow soda ash; 0.5ml water and 50mg (0.04mmol) four triphenyl phosphorus palladiums; under the nitrogen protection in toluene 90 ℃ the reaction 36h; be cooled to room temperature then; removal of solvent under reduced pressure, column chromatography for separation get 20 (298.8mg, productive rates 60%).MS：m/z：1423([M+H]
+)。
The preparation of embodiment 11 compounds 21
In the 50ml two-mouth bottle, add 500mg (0.35mmol) intermediate 2 and 250mg (2.1mmol) 2-thienyl boric acid; 658mg (7mmol) yellow soda ash; 0.5ml water and 50mg (0.04mmol) four triphenyl phosphorus palladiums; under the nitrogen protection in toluene 90 ℃ the reaction 36h; be cooled to room temperature then; removal of solvent under reduced pressure, column chromatography for separation get 21 (305mg, productive rates 70%).MS：m/z：1247([M+H]
+)。
The preparation of embodiment 12 compounds 23
In the 50ml two-mouth bottle, add 500mg (0.35mmol) intermediate 2 and 360mg (2.1mmol) 22; 658mg (7mmol) yellow soda ash; 0.5ml water and 50mg (0.04mmol) four triphenyl phosphorus palladiums; under the nitrogen protection in toluene 90 ℃ the reaction 48h; be cooled to room temperature then; removal of solvent under reduced pressure, column chromatography for separation get 23 (382mg, productive rates 75%).MS：m/z：1455([M+H]
+)。
Claims (2)
1. a class 1,6,7,12-Si Ben Ji perylene double imide derivative, it is characterized in that: such structural general formula is as follows:
Wherein: R is selected from carbazyl, 3,6-di-t-butyl carbazyl, 3,6-two (3,6-di-t-butyl carbazyl) carbazyl, naphthyl, anthryl, phenanthryl, pyrenyl, N-phenyl-1-naphthylamine base, thienyl, pyrazinyl, diazosulfide base or the following group of general structure:
R1～R4 all is pentafluorophenyl group or R1=R4=phenyl, the phenyl that the R base of R2=R3=except that A, B replaces;
The straight chain of R '=C8-C12, branched-chain alkyl or perfluoroalkyl, the general structure of perfluoroalkyl are CF3 (CF2) nCF2, the even number of n=2～10.
2. according to the described class 1,6,7 of claim 1, the preparation method of 12-Si Ben Ji perylene double imide derivative, it is characterized in that: this preparation method may further comprise the steps:
(1) with 1,6,7, the 12-tetraphenyl replaces De perylene double imide and mixes at 1: 2.5: 2 with mol ratio with two (trifluoroacetic acid) iodobenzene, iodine, and room temperature reaction 8h in tetracol phenixin gets 1,6,7, and four pairs of iodophenyls of 12-replace De perylene double imide;
(2) with the product of trimethylsilyl acetylene and step (1), with [PdCl2 (PPh3) 2], cuprous iodide and triphenyl phosphorus 4.8: 1: 0.2 in molar ratio: mix at 0.5: 0.5, in volume ratio is 2～3: 1 triethylamine and tetrahydrofuran solution, nitrogen protection is reacted 5～24h down for 25～40 ℃, generate 1,6,7,12-four is to (trimethylsilyl acetylene base) Ben Ji perylene double imide, be that room temperature reaction 2～6h sloughs protecting group and gets the peripheral perylene double imide that has four ethynyl active groups under 50: 1 the Neutral ammonium fluoride and the effect of tetra-n-butyl Neutral ammonium fluoride with after product in mol ratio;
(3) with two Propiophenones and 4,4 '-dibromo benzil is in ethanol solution, back flow reaction half an hour under the potassium hydroxide effect, obtain the cyclopentadienone of two bromos, then with itself and 3,6-di-t-butyl carbazole or N-phenyl-1-naphthylamine, copper powder or cuprous iodide, 18-hat-6, Anhydrous potassium carbonate 1: 3: 2 in molar ratio: mix at 0.2: 6, under the nitrogen protection, 150～200 ℃ of reaction 5～72h obtain containing the cyclopentadienone of different substituents in oil of mirbane;
(4) with the product and 3 of step (1), 6-di-t-butyl carbazole or N-phenyl-1-naphthylamine etc., cuprous iodide, 18-hat-6, Anhydrous potassium carbonate 1: 6: 4 in molar ratio: mix at 0.4: 12, in oil of mirbane, react 5～35h under the nitrogen protection and obtain corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative; Or the product of step (1) and naphthalene boronic acids, thienyl boric acid or diazosulfide boric acid are obtained by the Suzuki reaction corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative; Or the product of step (2) mixed with the product 1: 4.8 in molar ratio～12 of step (3), in o-Xylol, 160～170 ℃ of reactions 1～3 day down, obtain corresponding 1,6,7,12-Si Ben Ji perylene double imide derivative.
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Application publication date: 20100310 |