CN103044244A - Pyrene D-pi-A type asymmetric disc dye compound - Google Patents
Pyrene D-pi-A type asymmetric disc dye compound Download PDFInfo
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Abstract
The invention relates to a pyrene D-pi-A type asymmetric disc dye compound, and a preparation method of a pyrene derivative material. A length-controllable flexible chain of the asymmetric pyrene derivative material serves as a donator (alkyl or alkoxy phenylacetylene and bis-alkylaniline), and a carboxy side chain serves as a receptor (benzoic acid or iso-cyanoacrylate). The prominent advantages of the pyrene disc compound applied to a dye-sensitized solar cell are simple synthesis and separation, low cost, better photoelectric conversion efficiency, and the like. In addition, electron-withdrawing and electron-donating groups are added through a coupled reaction to form the asymmetric D-pi-A type disc dye compound, and the problem of efficiency reduction caused by dye molecular aggregation is solved by controlling positions of the electron-withdrawing and electron-donating groups. The compound has very high ultraviolet absorption and photoelectric conversion efficiency, and has a wide application prospect in organic-dye-sensitized solar cells.
Description
Technical field
The invention belongs to the organic photoelectrical material field, relate to an a kind of class pyrene class D-π-asymmetric plate-like dye composition of A type with certain photoelectric transformation efficiency.
Background technology
Entered since 20th century, be accompanied by developing rapidly of human industrial civilization, the mineral wealth such as coal, oil, Sweet natural gas are day by day exhausted, and the energy dilemma and the environmental pollution that cause have thus become the serious problems that need to be resolved hurrily.That sun power has is inexhaustible, nexhaustible, safe and reliable, pollution-free, be not subjected to the plurality of advantages such as geographical environment restriction, more and more in widespread attention.And organic solar batteries is extensive with its material source, cost of manufacture is low, power consumption less, flexible, be easy to the outstanding advantage such as scale operation and shown its huge potentiality to be exploited, become the in recent ten years focus of each colleges and universities and R﹠D institution research both at home and abroad.
Dye sensitization solar battery has higher transformation efficiency, improvement direction in the numerous organic solar batteries of at present research: novel, the exploration of suitable sensitizing agent, preparation technology's improvement and the research of nanometer filming may become another focus.
The pyrene molecule has very high fluorescence quantum efficiency and dark blue light emission as a large condensed ring, is widely used at biology.From device, it can improve the mobility of material and the performance that the hole is injected.These character of pyrene are so that they get a good chance of becoming photoelectric material, but relevant research but seldom.
Summary of the invention
The object of the present invention is to provide a class asymmetric D-π-A type pyrene analog derivative material and preparation method thereof.Introduce and to body and acceptor groups, the product solvability is better, is easy to synthesize, separate at the pyrene ring with linked reaction, with low cost and have a preferably photoelectric transformation efficiency; By give, the control of electrophilic group position, overcome that dye molecule is assembled and the Efficiency Decreasing problem that causes.
Technical scheme of the present invention is: the chemical structure of this compound, structure is shown in general formula (1).
Wherein, R
1Be selected from alkyl or alkoxy benzene class, its structure is:
Be selected from: the combination of phenylformic acid or class alpha-cyanoacrylate class and alkyl or alkoxy benzene acetylene class, two alkylbenzene amines, and have a R at least
2Be phenylformic acid or class alpha-cyanoacrylate class substituting group,
Its structure is:
The reaction mechanism of compound of the present invention is:
Above-mentioned pyrene class is the preparation method of D-π-asymmetric plate-like dye composition of A type not, it is characterized in that, the method has following steps:
The bromo-reaction of A pyrene: pyrene is dissolved in the oil of mirbane, places in the reactor, drip gradually 2 equivalents (or 3 equivalents) bromine under the room temperature, after dripping, temperature is raised to the 100-120 degree, react stopped reaction after 16-24 hour.Product poured into stir in the solution that fills sodium bisulfite and remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got bromination product.
B Sonogashira linked reaction: be dissolved in tetrahydrofuran (THF) and the Diisopropylamine mixing solutions obtaining product among the A, place reactor to lead to argon shield, then add the end alkynyl radical trimethyl silicane of 4-6 equivalent, be warmed up to the 80-120 degree; The triphenyl phosphorus palladium chloride that adds the 2-5% equivalent, cuprous iodide.Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, crossing the pillar developping agent after the underpressure distillation desolventizing is the mixed solvent of normal hexane and methylene dichloride 1:1.Get faint yellow product.
C connects to precursor reactant: bromo pyrene class product is dissolved in tetrahydrofuran (THF) and the Diisopropylamine mixing solutions, places reactor to lead to argon shield, then add the 3-6 equivalent to the phenylacetylene class to body, be warmed up to the 80-120 degree; The triphenyl phosphorus palladium chloride that adds the 2-5% equivalent, cuprous iodide.Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is normal hexane and methylene dichloride 1:1 with product.Get yellow product.
D connects the iodo receptor response: bromo pyrene class product is dissolved in tetrahydrofuran (THF) and the Diisopropylamine mixing solutions, places reactor to lead to argon shield, then add the iodo carboxylic acid acceptor of 3-6 equivalent, be warmed up to the 80-120 degree; The triphenyl phosphorus palladium chloride that adds the 2-5% equivalent, cuprous iodide.Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is ethyl acetate and normal hexane 1:1 with product.Get the safran final product.
The invention has the beneficial effects as follows: the present invention contains different alkyl or alkoxy benzene acetylene class, two alkylbenzene amine to body by Sonogashira linked reaction access; And phenylformic acid or class alpha-cyanoacrylate receptoroid, form D-π-asymmetric plate-like dyestuff of A type.The advantages such as it has the preparation of being easy to, and synthesis technique is simple, and route is short, and cost is low have very strong uv-absorbing and photoelectric transformation efficiency simultaneously; By linked reaction to claim 2,3 related give, the control of electrophilic group position, overcome that dye molecule is assembled and the Efficiency Decreasing problem that causes.This compound has very strong uv-absorbing and photoelectric transformation efficiency, and this compounds just organic dye sensitized solar cell aspect is with a wide range of applications.
Description of drawings
Fig. 1 is the uv-spectrogram of molecule described in the embodiment 1.
Fig. 2 is the J-V curve of molecule described in the embodiment 1.
Fig. 3 is the uv-spectrogram of molecule described in the embodiment 2.
Fig. 4 is the J-V curve of molecule described in the embodiment 2.
Fig. 5 is the uv-spectrogram of molecule described in the embodiment 3.
Fig. 6 is the J-V curve of molecule described in the embodiment 3.
Fig. 7 is the structural representation of the compounds of this invention general formula.
Embodiment
Below in conjunction with specific embodiment technical scheme of the present invention is described further.
Embodiment 1:
With: R
1Structure is
R
2Structure is
Introduce the synthetic method of this compound for example
The bromo-reaction of A pyrene: 10mmol pyrene (2.02g) is dissolved in the 50mL oil of mirbane, places in the 100mL single port bottle, drip gradually 30mmol bromine (2.00mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, react stopped reaction after 16-24 hour.Product poured into to fill in the solution that 200mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got yellow powder product 2.81g, productive rate 78%.
B Sonogashira linked reaction: be dissolved in 30mL tetrahydrofuran (THF) and the 30mL Diisopropylamine mixing solutions obtaining 5mmol product (1.80g) among the A, place the 100mL bottle with two necks to lead to argon shield, then add 25mmol end alkynyl radical trimethyl silicane (3mL), be warmed up to the 80-120 degree; Add 0.2mmol triphenyl phosphorus palladium chloride (140.00mg), 0.2mmol cuprous iodide (38mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, crossing the pillar developping agent after the underpressure distillation desolventizing is the mixed solvent of normal hexane and methylene dichloride 1:1.Get faint yellow product 1.62g, productive rate 82%.
The bromo-reaction of C intermediate product: the 4mol product (1.58g) that obtains among the B is dissolved in the 50mL oil of mirbane, place in the 100mL single port bottle, drip gradually 10mmol bromine (1mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, reacts stopped reaction after 16-24 hour.Product poured into to fill in the solution that 100mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got bromo intermediate product 1.76g, productive rate 80%.
D connects to precursor reactant: the 3mol product (1.66g) that obtains among the step C is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then the 8mmol that adds is warmed up to the 80-120 degree to amyl phenyl ether acetylene (1.41g); Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is normal hexane and methylene dichloride 1:1 with product.Get safran product 1.59g, productive rate 71%.
E goes the trimethyl silicane reaction: product among the step D is dissolved in methyl alcohol and the tetrahydrofuran solution, places the rear salt of wormwood that adds of reactor, stirred 3-8 hour under the room temperature, and then underpressure distillation desolventizing, washing, methyl alcohol is washed; Nitrogen protection in the container after the vacuum-drying.
F connects the iodo receptor response: the 2mmol product (1.24g) that obtains in the step F is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then add 6mmol 4-Iodobenzoic acid (1.49g), be warmed up to the 80-120 degree; Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is ethyl acetate and normal hexane 1:1 with product.Get orange final product 899mg, productive rate 54%.
Embodiment 2:
With R
1Structure is
R
2Structure is
Introduce the synthetic method of this compound for example
The bromo-reaction of A pyrene: 10mmol pyrene (2.02g) is dissolved in the 50mL oil of mirbane, places in the 100mL single port bottle, drip gradually 30mmol bromine (2.00mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, react stopped reaction after 16-24 hour.Product poured into to fill in the solution that 200mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got yellow powder product 2.81g, productive rate 78%.
B Sonogashira linked reaction: be dissolved in 30mL tetrahydrofuran (THF) and the 30mL Diisopropylamine mixing solutions obtaining 5mmol product (1.80g) among the A, place the 100mL bottle with two necks to lead to argon shield, then add 25mmol end alkynyl radical trimethyl silicane (3mL), be warmed up to the 80-120 degree; Add 0.2mmol triphenyl phosphorus palladium chloride (140.00mg), 0.2mmol cuprous iodide (38.00mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, crossing the pillar developping agent after the underpressure distillation desolventizing is the mixed solvent of normal hexane and methylene dichloride 1:1.Get faint yellow product 1.62g, productive rate 82%.
The bromo-reaction of C intermediate product: the 4mol product (1.58g) that obtains among the B is dissolved in the 50mL oil of mirbane, place in the 100mL single port bottle, drip gradually 10mmol bromine (1mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, reacts stopped reaction after 16-24 hour.Product poured into to fill in the solution that 100mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got bromo intermediate product 1.76g, productive rate 80%.
D connects to precursor reactant: the 3mol product (1.66g) that obtains among the step C is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then the 8mmol4-acetylene-N that adds, N-diamyl aniline (2.06g) is warmed up to the 80-120 degree; Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is normal hexane and methylene dichloride 1:1 with product.Get safran product 1.65g, productive rate 72%.
E goes the trimethyl silicane reaction: product among the step D is dissolved in methyl alcohol and the tetrahydrofuran solution, places the rear salt of wormwood that adds of reactor, stirred 3-8 hour under the room temperature, and then underpressure distillation desolventizing, washing, methyl alcohol is washed; Nitrogen protection in the container after the vacuum-drying.
F connects the iodo receptor response: the 2mmol product (1.24g) that obtains in the step F is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then add 6mmol 4-Iodobenzoic acid (1.49g), be warmed up to the 80-120 degree; Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is ethyl acetate and normal hexane 1:1 with product.Get orange final product 99.98mg, productive rate 58%.
Embodiment 3:
With R
1Structure is
R
2Structure is
Introduce the synthetic method of this compound for example
The bromo-reaction of A pyrene: 10mmol pyrene (2.02g) is dissolved in the 50mL oil of mirbane, places in the 100mL single port bottle, drip gradually 30mmol bromine (2.00mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, react stopped reaction after 16-24 hour.Product poured into to fill in the solution that 200mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got yellow powder product 2.81g, productive rate 78%.
B Sonogashira linked reaction: be dissolved in 30mL tetrahydrofuran (THF) and the 30mL Diisopropylamine mixing solutions obtaining 5mmol product (1.80g) among the A, place the 100mL bottle with two necks to lead to argon shield, then add 25mmol end alkynyl radical trimethyl silicane (3mL), be warmed up to the 80-120 degree; Add 0.2mmol triphenyl phosphorus palladium chloride (140.00mg), 0.2mmol cuprous iodide (38.00mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, crossing the pillar developping agent after the underpressure distillation desolventizing is the mixed solvent of normal hexane and methylene dichloride 1:1.Get faint yellow product 1.62g, productive rate 82%.
The bromo-reaction of C intermediate product: the 4mol product (1.58g) that obtains among the B is dissolved in the 50mL oil of mirbane, place in the 100mL single port bottle, drip gradually 10mmol bromine (1mL) under the room temperature, after dripping, temperature is raised to the 100-120 degree, reacts stopped reaction after 16-24 hour.Product poured into to fill in the solution that 100mL concentration is 10% sodium bisulfite to stir remove the residue bromine, changed water once every ten minutes, until solution is colourless; Separatory is removed water layer, adds methyl alcohol generation particulate state precipitation in organic layer, filters after washing and ethanol and washes, and drying had both got bromo intermediate product 1.76g, productive rate 80%.
D connects to precursor reactant: the 3mol product (1.66g) that obtains among the step C is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then the 8mmol that adds is warmed up to the 80-120 degree to amylbenzene acetylene (1.38g); Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is normal hexane and methylene dichloride 1:1 with product.Get safran product 1.57g, productive rate 71%.
E goes the trimethyl silicane reaction: product among the step D is dissolved in methyl alcohol and the tetrahydrofuran solution, places the rear salt of wormwood that adds of reactor, stirred 3-8 hour under the room temperature, and then underpressure distillation desolventizing, washing, methyl alcohol is washed; Nitrogen protection in the container after the vacuum-drying.
F connects the iodo receptor response: the 2mmol product (1.52g) that obtains in the step F is dissolved in 20mL tetrahydrofuran (THF) and the 20mL Diisopropylamine mixing solutions, place 100mL single port bottle to lead to argon shield, then add 6mmol to iodobenzene alpha-cyanoacrylate (1.80g), be warmed up to the 80-120 degree; Add 0.1mmol triphenyl phosphorus palladium chloride (70.00mg), 0.1mmol cuprous iodide (19mg).Under the argon shield back flow reaction 12-16 hour.Behind the stopped reaction, the underpressure distillation desolventizing is crossed the mixed solvent that the pillar developping agent is ethyl acetate and normal hexane 1:1 with product.Get orange final product 1.06g, productive rate 48%.
Table 1 and table 2 are photoelectric properties of each compound
Claims (1)
1. a class pyrene class D-π-asymmetric plate-like dye composition of A type is characterized in that, the chemical structure of this compound, and structure is shown in general formula (1).
Wherein, R
1Be selected from alkyl or alkoxy benzene class, its structure is:
Its structure is:
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107973536A (en) * | 2017-11-16 | 2018-05-01 | 江苏苏博特新材料股份有限公司 | A kind of oligomeric-type concrete defoamer, its preparation method and application |
| US10583972B2 (en) | 2016-06-07 | 2020-03-10 | International Business Machines Corporation | Polymer with blue light absorbing units chemically bonded to a polyermic backbone of the polymer |
| CN111748216A (en) * | 2020-06-28 | 2020-10-09 | 苏州美嘉写智能显示科技有限公司 | Synthetic method for preparing novel pyrene D-pi-A type solar cell dye through click reaction |
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| CN101072743A (en) * | 2004-11-25 | 2007-11-14 | 日本先锋公司 | Pyrene compound and, utilizing the same, light emitting transistor device and electroluminescence device |
| JP2010106084A (en) * | 2008-10-28 | 2010-05-13 | Univ Of Tokyo | Liquid crystal material, compound, piezochromic light-emitting material, liquid crystal material film, coating material, and method for producing liquid crystal material film |
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Patent Citations (2)
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| CN101072743A (en) * | 2004-11-25 | 2007-11-14 | 日本先锋公司 | Pyrene compound and, utilizing the same, light emitting transistor device and electroluminescence device |
| JP2010106084A (en) * | 2008-10-28 | 2010-05-13 | Univ Of Tokyo | Liquid crystal material, compound, piezochromic light-emitting material, liquid crystal material film, coating material, and method for producing liquid crystal material film |
Non-Patent Citations (1)
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| YEON OK LEE ET AL.: "Enhanced Electrogenerated Chemiluminescence of Phenylethynylpyrene Derivatives: Use of Weakly Electron-Donating Group as a Substituent", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10583972B2 (en) | 2016-06-07 | 2020-03-10 | International Business Machines Corporation | Polymer with blue light absorbing units chemically bonded to a polyermic backbone of the polymer |
| CN107973536A (en) * | 2017-11-16 | 2018-05-01 | 江苏苏博特新材料股份有限公司 | A kind of oligomeric-type concrete defoamer, its preparation method and application |
| CN111748216A (en) * | 2020-06-28 | 2020-10-09 | 苏州美嘉写智能显示科技有限公司 | Synthetic method for preparing novel pyrene D-pi-A type solar cell dye through click reaction |
| CN111748216B (en) * | 2020-06-28 | 2021-12-31 | 苏州美嘉写智能显示科技有限公司 | Synthetic method for preparing novel pyrene D-pi-A type solar cell dye through click reaction |
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