CN103739593A - Perylene monoimide dimers and preparation method thereof - Google Patents

Perylene monoimide dimers and preparation method thereof Download PDF

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CN103739593A
CN103739593A CN201310618983.0A CN201310618983A CN103739593A CN 103739593 A CN103739593 A CN 103739593A CN 201310618983 A CN201310618983 A CN 201310618983A CN 103739593 A CN103739593 A CN 103739593A
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preparation
reaction
perylene
alkane
list imide
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肖义
张有地
王赫麟
赵振博
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Dalian University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

The invention relates to a class of perylene monoimide dimers and a preparation method thereof, wherein in the structural general formula (as the follow), R1 is H, C1-C20 alkane and other groups represented by the following formulas, Ar is a group represented by the following formulas, n is 1, 2 or 3, R2, R4 and R5 are H and C1-C20 alkane, and R3 is CH3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)CH2CH3, phenyl or a group represented by the following formula. The preparation method comprises: carrying out a Suzuki coupling reaction of perylene monoimide borate or perylene monoimide tributyltin and dibromo aromatic hydrocarbon to prepare the perylene monoimide dimer. The prepared perylene monoimide dimer has characteristics of good dye property, excellent solubility in organic solvents, good wide and long wavelength absorption in near- infrared regions, high fluorescence quantum yield, good oxidation reduction property, excellent electron transmission property, and outstanding organic solar cell performance.

Description

Yi Lei perylene list imide dimer and preparation method thereof
Technical field
The present invention relates to organic synthesis field, be specifically related to Yi Lei perylene list imide dimer and preparation method thereof.
Background technology
Perylene list imide is the dyestuff that a class has large planar rigidity conjugated backbone; ， perylene list imide derivative has developed a variety of at present.Wherein, 2 kinds of important Zhong Jian Ti perylene list imide boric acid esters are with perylene list imide tributyl tin is utilized (Nolde F., Pisula W., M ü llen K., et al., Chem.Mater., 2006,18,3715-3725 widely; Geerts Y., Quante H., M ü llen K., et al., J.Mater.Chem., 1998,8,2357 – 2369).We are with document Cremer J., Mena-Osterit E.,
Figure BDA0000424001370000011
the synthetic thinking of P.et al is foundation.Therefore perylene list imide dimer is synthesized efficiently, be mainly by the dye molecule in perylene list imide dimer with the non-conjugated system of the large plane of a special class, it is synthetic is to lead to perylene list imide boric acid ester or person's perylene list imide tributyl tin and contained class two bromos or the preparation of two iodo aromatic hydrocarbons process Suzuki linked reaction.And in the region of visible ray, there is strong π-π * broad absorption band, Qi perylene list imide dimer molecule of characteristics of luminescence of well having given prominence to dyestuff itself is widely used in organic semiconductor field, the aspects such as such as organic thin film solar cell, organic field effect tube, electroluminescent diode, organic laser, fluorescent probe and liquid-crystal display.Therefore, at industrialization field ， perylene list imide and derivative, there is good researching value.The research and development of its new texture and application have certain theory and realistic meaning.
Summary of the invention
The object of the invention is its synthetic dimeric molecular application of Yi Lei perylene list imide in organic semiconductor field, for example typical organic solar batteries aspect.And be devoted to study shla molecule, and then utilize the method for solution processing to be manufactured with the heterogeneous node solar battery of body.And its optical property also has wide and near infrared absorption band in visible region.
The invention provides the logical formula I of a class perylene list imide dimer
In formula, R 1for H, C 1～C 20straight-chain paraffin, C 1～C 20branched paraffin,
Figure BDA0000424001370000022
Figure BDA0000424001370000023
ar=
Figure BDA0000424001370000024
wherein, n=1,2 or 3; R 2for H, C 1～C 20straight-chain paraffin or C 1～C 20branched paraffin; R 3for CH 3, CH (CH 3) 2, CH 2cH (CH 3) 2, CH (CH 3) CH 2cH 3, phenyl or
Figure BDA0000424001370000025
r 4and R 5for H, C 1～C 20straight-chain paraffin or C 1～C 20branched paraffin.
Logical formula I compound can be prepared according to following flow process:
(1)
Figure BDA0000424001370000026
(2)
In formula, X=Br or I; R 1=H, C 1～C 20straight-chain paraffin, C 1～C 20branched paraffin,
Figure BDA0000424001370000028
Figure BDA0000424001370000029
ar=
Figure BDA0000424001370000031
Wherein, n=1,2 or 3; R 2for H, C 1～C 20straight-chain paraffin or C 1～C 20branched paraffin; R 3=CH 3, CH (CH 3) 2, CH 2cH (CH 3) 2, CH (CH 3) CH 2cH 3, phenyl or
Figure BDA0000424001370000032
r 4and R 5for H, C 1～C 20straight-chain paraffin or C 1～C 20branched paraffin.
In the present invention, the dimeric preparation method of Yi Lei perylene list imide is as follows:
Take the compound that leads to formula IV and the aromatic hydrocarbon that contains dibromo as raw material, they are take mol ratio as 1:1～10, Pd (PPh 3) 4, Pd (PPh 3) 2cl 2, Pd (dppf) Cl 2or Pd (CH 3cOO) 2for catalyzer, the mol ratio of dibromo aromatic hydrocarbon and catalyzer is 1:0.01～0.1, the K of 0.1-1M 2cO 3, Na 2cO 3, CH 3cOOK or K 2hPO 4as alkali, 60～150 ℃ of conditions, stirring reaction 2～30h in organic solvent, Suzuki linked reaction obtains the perylene list imide dimeric dyes of logical formula I.Wherein organic solvent is selected from toluene, chloroform, N-Methyl pyrrolidone, quinoline, imidazoles, chlorobenzene, 1, one or more in 2-dichlorobenzene, ethylene glycol monomethyl ether or glycol dimethyl ether, glacial acetic acid, propionic acid, tetrahydrofuran (THF).
The dyestuff making as stated above can separate by any ordinary method, and such as solution weight crystallization, precipitation and filtration, spraying are dry etc.
The invention has the beneficial effects as follows and based on a lot of dye molecules, at aspects such as organic thin film solar cell, organic field effect tube, electroluminescent diode, organic laser, fluorescent probe and liquid-crystal displays, there is application widely.Therefore, we are applied to organic thin film solar cell Jiang perylene list imide dimer, and effciency of energy transfer is 0.53%-1.35%; The present invention prepares perylene list imide dimer and can be applicable to organic thin film solar cell etc. and relative purposes.
Accompanying drawing explanation
Fig. 1 is the abosrption spectrogram of embodiment 1 product.
Fig. 2 is the organic solar I-V figure of embodiment 1 product.
Fig. 3 is external quantum efficiency figure.
Embodiment
Below in conjunction with technical scheme and accompanying drawing, describe specific embodiments of the invention in detail.
Embodiment 1
n-9'-octyl group-3,6-dibromo carbazole (1mmol), compound 1(2.4mmol), CH 3cOOK(2mmol), Pd (PPh 3) 4(2%mmol), be dissolved in 4mL toluene and 2mL H 2the mixed solvent of O, is heated to back flow reaction 17h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 88%.HRMS:1237.5758（m/z）。
Embodiment 2
Figure BDA0000424001370000042
9,9-dioctyl-2,7-dibromo fluorenes (1mmol), compound 2(1.5mmol), K 2hPO 4(1.5mmol), Pd (PPh 3) 2cl 2(1.5%mmol), be dissolved in 2mL quinoline and 1mL H 2the mixed solvent of O, is heated to back flow reaction 15h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 84%.HRMS:1348.7057（m/z）。
Embodiment 3
Figure BDA0000424001370000043
n-9'-17 carbon back-2,7-diiodocarbazol (3mmol), compound 3(6.7mmol), Na 2cO 3(4mmol), Pd (dppf) Cl 2(4%mmol), be dissolved in 8mL1,2-dichlorobenzene and 4mL H 2the mixed solvent of O, is heated to back flow reaction 20h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 80%.HRMS:2627.1305（m/z）。
Embodiment 4
Figure BDA0000424001370000051
9,9-dihexyl-2,7-dibromo fluorenes (5mmol), compound 4(12mmol), K 2cO 3(6mmol), Pd (CH 3cOO) 2(4%mmol), be dissolved in 13mL chloroform and 6.5mL H 2the mixed solvent of O, is heated to back flow reaction 22h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 87%.HRMS:1533.0187（m/z）。
Embodiment 5
Figure BDA0000424001370000052
paradibromobenzene (3.5mmol), compound 5(7mmol), K 2hPO4(5mmol), Pd (dppf) Cl 2(3%mmol), be dissolved in 10mL N-Methyl pyrrolidone and 5mL H 2the mixed solvent of O, is heated to back flow reaction 16h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 82%.HRMS:1196.5915（m/z）。
Embodiment 6
Figure BDA0000424001370000053
3-hexyl-2,5-thiophene biniodide (2.5mmol), compound 6(6mmol), K 2cO 3(3.5mmol), Pd (CH 3cOO) 2(2.5%mmol), be dissolved in 7mL ethylene glycol monomethyl ether and 3.5mL H 2the mixed solvent of O, is heated to back flow reaction 14h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 79%.HRMS:2350.8501（m/z）。
Embodiment 7
Figure BDA0000424001370000061
9,9-dibutyl-2,7-dibromo fluorenes (3mmol), compound 7(8mmol), CH 3cOOK(5mmol), Pd (CH 3cOO) 2(2.5%mmol), be dissolved in 6mL THF and 3mL H 2the mixed solvent of O, is heated to back flow reaction 11h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 84%.HRMS:1394.7799（m/z）。
Embodiment 8
Figure BDA0000424001370000062
n-9'-octyl group-3,6-dibromo carbazole (2mmol), compound 8(6mmol), K 2hPO 4(4mmol), Pd (PPh 3) 4(1%mmol), be dissolved in 2mL THF and 1mL H 2the mixed solvent of O, is heated to back flow reaction 14h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 75%.HRMS:1339.7126（m/z）。
Embodiment 9
Figure BDA0000424001370000063
9,9-diethyl-2,7-diiodo-fluorenes (8mmol), compound 9(20mmol), Na 2cO 3(8mmol), Pd (PPh 3) 2cl 2(5%mmol), be dissolved in 12mL glycol dimethyl ether and 6mL H 2the mixed solvent of O, is heated to back flow reaction 24h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 70%.HRMS:2315.8288（m/z）。
Embodiment 10
Figure BDA0000424001370000071
n-9'-11 carbon back-2,7-dibromo carbazole (4mmol), compound 10(10mmol), K 2hPO 4(4mmol), Pd (CH 3cOO) 2(2.5%mmol), be dissolved in 5mL propionic acid and 2.5mL H 2the mixed solvent of O, is heated to back flow reaction 20h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 78%.HRMS:1296.6704（m/z）。
Embodiment 11
9,9-dihexyl-2,7-dibromo fluorenes (4mmol), compound 11(10mmol), K 2cO 3(4mmol), Pd (PPh 3) 4(2.5%mmol), be dissolved in 5mL acetic acid and 2.5mL H 2the mixed solvent of O, is heated to back flow reaction 20h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 78%.HRMS:1308.7683（m/z）。
Embodiment 12
n-9'-butyl-3,6-diiodocarbazol (4mmol), compound 12(10mmol), K 2hPO 4(4mmol), Pd (dppf) Cl 2(2.5%mmol), be dissolved in 5mL THF and 2.5mL H 2the mixed solvent of O, is heated to back flow reaction 20h.Reaction finishes rear dichloromethane extraction, and washing and drying is concentrated, and column chromatography chromatogram separates and obtains product red solid, productive rate 78%.HRMS:2118.7236（m/z）。

Claims (10)

1. Yi Lei perylene list imide dimer, its general structure is:
Figure FDA0000424001360000011
In formula, R 1for H, C 1～C 20alkane,
Figure FDA0000424001360000012
Ar is
Figure FDA0000424001360000014
Wherein, n=1,2 or 3; R 2, R 4and R 5for H, C 1～C 20alkane; R 3=CH 3, CH (CH 3) 2, CH 2cH (CH 3) 2, CH (CH 3) CH 2cH 3, phenyl or
Figure FDA0000424001360000015
2. the dimeric preparation method of Yi Lei perylene list imide described in claim 1, it is characterized in that passes through Suzuki linked reaction Jiang perylene list imide boric acid ester Huo perylene list imide tributyl tin and dibromo aromatic hydrocarbon, get perylene list imide dimer processed, concrete reaction expression is:
(1) perylene list imide boric acid ester and dibromo aromatic hydrocarbon are by Suzuki linked reaction
Figure FDA0000424001360000016
(2) perylene list imide tributyl tins and dibromo aromatic hydrocarbon are by Suzuki linked reaction
In formula, X=Br or I; R 1for H, C 1～C 20alkane,
Figure FDA0000424001360000018
Figure FDA0000424001360000021
ar is
Figure FDA0000424001360000022
Wherein, n=1,2 or 3; R 2, R 4and R 5for H, C 1～C 20alkane; R 3=CH 3, CH (CH 3) 2, CH 2cH (CH 3) 2, CH (CH 3) CH 2cH 3, phenyl or
Figure FDA0000424001360000024
3. preparation method according to claim 2, is characterized in that, the catalyzer that preparation process is used is Pd (PPh 3) 4, Pd (PPh 3) 2cl 2, Pd (dppf) Cl 2or Pd (CH 3cOO) 2.
4. according to the preparation method described in claim 2 or 3, it is characterized in that, the mol ratio of described dibromo aromatic hydrocarbon and the catalyzer of application is 1:0.01～0.1.
5. according to the preparation method described in claim 2 or 3, it is characterized in that the K that the alkali that preparation process is used is 0.1-1M 2cO 3, Na 2cO 3, CH 3cOOK or K 2hPO 4.
6. preparation method according to claim 4, is characterized in that, the K that the alkali that preparation process is used is 0.1-1M 2cO 3, Na 2cO 3, CH 3cOOK or K 2hPO 4.
7. according to the preparation method described in claim 2,3 or 6, it is characterized in that, temperature of reaction is 60～150 ℃.
8. preparation method according to claim 4, is characterized in that, reaction bar temperature is 60～150 ℃.
9. preparation method according to claim 5, is characterized in that, temperature of reaction is 60～150 ℃.
10. according to the preparation method described in claim 2,3,6,8 or 9, it is characterized in that, the organic solvent adding in reaction is selected from toluene, chloroform, N-Methyl pyrrolidone, quinoline, imidazoles, chlorobenzene, 1, one or more mixing in 2-dichlorobenzene, ethylene glycol monomethyl ether, glycol dimethyl ether, glacial acetic acid, propionic acid, tetrahydrofuran (THF).
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107759622A (en) * 2017-10-17 2018-03-06 大连理工大学 A kind of triphendioxazine acid imide diploid compound and preparation method thereof
CN110642870A (en) * 2019-09-30 2020-01-03 汕头大学 NTI monomer and preparation method thereof, polymer PNTB1 thereof, and preparation method and application thereof

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107759622A (en) * 2017-10-17 2018-03-06 大连理工大学 A kind of triphendioxazine acid imide diploid compound and preparation method thereof
CN110642870A (en) * 2019-09-30 2020-01-03 汕头大学 NTI monomer and preparation method thereof, polymer PNTB1 thereof, and preparation method and application thereof
CN110642870B (en) * 2019-09-30 2022-01-04 汕头大学 NTI monomer and preparation method thereof, polymer PNTB1 thereof, and preparation method and application thereof

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Application publication date: 20140423