CN102617834A - Soluble poly-5,10-phenanthrene thiophene and preparing method and application thereof - Google Patents
Soluble poly-5,10-phenanthrene thiophene and preparing method and application thereof Download PDFInfo
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Abstract
The invention discloses soluble poly-5,10-phenanthrene thiophene and a preparing method and application thereof. The soluble poly-5,10-phenanthrene thiophene has the following structure, wherein R is an alkyl chain, and n is an integer which is larger than or equal to 1. The preparing method includes: leading 2,7-dibromo phenanthraquinone and thiodiglycolicacid methyl acetate to react to obtain 5,10-dibromo phenanthrene thiophene; and converting 5,10-dibromo phenanthrene thiophene to corresponding boric acid ester through Miyaura reaction, and leading the 5,10-dibromo phenanthrene thiophene and the boric acid ester of the 5,10-dibromo phenanthrene thiophene to perform a polymerization reaction to obtain the poly-5,10-phenanthrene thiophene. The soluble poly-5,10-phenanthrene thiophene and the preparing method and the application thereof have the advantages that material synthesizing raw materials are wide in source, the process is reliable and synthesizing steps are less. The poly-5,10-phenanthrene thiophene is soluble so that the poly-5,10-phenanthrene thiophene is suitable for spin coating or print filming and accordingly can be applied to the fields of electroluminescence, photovoltaic cells, non-linear optics and sensing.
Description
Technical field
The invention belongs to new functional macromolecule material, especially a kind of soluble poly 5,10-phenanthro-thiophene can be widely used in electroluminescent, photovoltaic cell, nonlinear optics and sensory field.
Background technology
The development of conjugated polymers comes from Japanese scientist Bai Chuanying tree synthetic polyacetylene film in 1977, can conduct electricity after the doping, is called as " the 4th generation macromolecular material ".Compare with the inorganic materials with identical or close purposes, conducting polymer has advantages such as low, the easy processing of density.Since the conjugate property of this type material structure, thus its ability transmission charge, stimulated luminescence can or possibly be applied on many electronics or opto-electronic device, like polymer LED, photovoltaic cell, FET etc.Potential application prospect and wide application field impel scientist competitively to study the conjugation material that this type has photoelectric activity, like polyacetylene, polypyrrole, Polythiophene, polyaniline, polyphenylene ethylene, gather fluorenes etc.
The present invention relates to a kind of novel conjugated polymers, gather 5,10-phenanthro-thiophene does not have bibliographical information at present.
Summary of the invention
The objective of the invention is to carry a kind of soluble poly 5; 10-phenanthro-thiophene; This polymkeric substance dissolves in all kinds of SOLVENTS because on the aryl substituted radical of long-chain is arranged, and is fit to spin coating or printing-filming, thereby is applied at photovoltaic cell, nonlinear optics and sensory field.
Simultaneously, the present invention also provides above-mentioned and gathers 5, the compound method of 10-phenanthro-thiophene.
The object of the invention is realized through following technical scheme:
Soluble poly 5,10-phenanthro-thiophene has following structure:
Wherein, R is an alkyl chain; N is >=1 integer.
Said R is the long-chain of C6～C20.
Said R is a kind of in the structure:
C
6H
13、C
8H
17、C
10H
21、C
12H
25、C
16H
33。
Said R is a kind of in the structure:
Said soluble poly 5, the preparation method of 10-phenanthro-thiophene: with 2,7-dibromo phenanthrenequione and the reaction of thiodiglycolic acid methyl esters obtain 5,10-dibromo phenanthro-thiophene; Again with 5,10-dibromo phenanthro-thiophene is converted into corresponding boric acid ester through the Miyaura reaction, and with 5,10-dibromo phenanthro-thiophene and its boric acid ester carry out polyreaction, obtain gathering 5,10-phenanthro-thiophene.
Said 5,10-phenanthro-thiophene is through Suzuki or the polymerization of Yamamoto method.
Gather 5,10-phenanthro-thiophene has big conjugation coplanar structure, and fluorenes class, polysilico fluorene class and polycarbazole base polymer band gap are narrow than gathering, and meet the requirement of solar cell donor material; Contain thiophene and carboxyl on its structure, this will help and soccerballene (PCBM) compatible.More than two big characteristics make and to gather 5 that 10-phenanthro-thiophene becomes novel solar cell material.
Advantage of the present invention has:
(1) material synthetic raw material sources are extensive, and technology is reliable.
(2) of the present inventionly gather 5,10-phenanthro-thiophene has solubility, thereby suitable spin coating or printing-filming, thereby is applied at electroluminescent, photovoltaic cell, nonlinear optics and sensory field.
Description of drawings
Fig. 1 .5,10-dibromo phenanthrenequione be [9,10-c] thiophene-1 also, the nucleus magnetic hydrogen spectrum of 3-dioctyl phthalate (2 '-ethylhexyl) ester;
Fig. 2 .5,10-dibromo phenanthrenequione be [9,10-c] thiophene-1 also, the nuclear-magnetism carbon spectrum of 3-dioctyl phthalate (2 '-ethylhexyl) ester;
Figure 3.5, 10 - phenanthrene quinone Pinacols knit the brows and [9,10-c] thiophene 1,3 - dicarboxylic acid (2'-ethylhexyl) phthalate H NMR;
Figure 4.5,10 - phenanthrene quinone Pinacols knit the brows and [9,10-c] thiophene 1,3 - dicarboxylic acid (2'-ethyl-hexyl) carbon nuclear magnetic resonance spectroscopy.
Embodiment
Below in conjunction with specific embodiment the present invention is done further concrete detailed description the in detail, but embodiment of the present invention is not limited thereto, the processing parameter for not indicating especially can carry out with reference to routine techniques.
Embodiment 1
(1) 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, the preparation of 3-dioctyl phthalate (2 '-ethylhexyl) ester
Synthetic route is following:
Get 250ml single port bottle I and connect constant pressure funnel and change nitrogen protection, add 1.68g potassium tert.-butoxide (t-BuOK) rapidly, inject 10ml methyl alcohol with syringe then, exothermic dissolution is put into cryosel with single port bottle I after the cooling and is bathed and stir.Other gets 250ml single port bottle II, takes by weighing 1.09g2, and 7-dibromo phenanthrenequione adds 60ml benzene, is heated to and stirs fully dissolving about 70 ℃.Be cooled to 0 ℃, 0.54g thiodiglycolic acid methyl esters is added among the above-mentioned single port bottle I, reaction solution becomes blue or green brown at once, removes cryosel bath nature and is warming up to stirring at room reaction 5d.
Stopped reaction behind the 5d, reaction solution are pale brown look turbid liquid.Aftertreatment is following: in reaction flask, add about 100ml water, stir, revolve except that organic solution, filter out undissolved solid; In filtrating, splash into HCl solution then, stir, have a large amount of yellow solid to separate out, continuing to drip HCl no longer increases to solids; Place 60 ℃ of oil baths to continue to stir 2h it is fully reacted, last suction filtration gets yellow solid, the dry product 1.30g 5 that gets; 10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, the 3-dioctyl phthalate.
With above-mentioned 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, and 3-dioctyl phthalate crude product joins in the 100ml single port bottle, adds 2 DMF, adds 8mlSOCl again
2, connecing prolong and drying tube and be heated to 80 ℃ of stirring reaction 6h, solids is dissolved as the reddish-brown clear liquor very soon.React decompression and extracted unnecessary SOCl
2, get pale brown look solid.In solids, add 10ml 2-ethylhexyl bromine (EHBr) then rapidly, be warming up to 100 ℃ and continue stirring reaction 2h, this moment, reaction solution became the brown clear liquid.Reacted decompression and extracted unnecessary EHBr, then with sherwood oil: ETHYLE ACETATE=20: 1 (volume ratio) is elutriant, and silica gel column chromatography purified product, recrystallizing methanol get 0.92g faint yellow solid thing, and this two steps productive rate together is 42%.
1H?NMR(400MHz，CDCl
3，ppm)：9.122(d，J＝1.2，2H)，8.162(d，J＝8.8，2H)，7.659(dd，J
1＝8.8，J
2＝1.2，2H)，4.385(m，4H)，1.779(m，2H)，1.488(m，4H)，1.422(m，4H)，1.344(m，8H)，0.973(t，6H)，0.902(t，6H).
13C?NMR(100MHz，CDCl
3，ppm)：162.851，136.739，131.515，130.844，129.461，128.826，127.954，124.552，121.544，68.941，38.949，30.569，29.002，24.011，23.009，14.071，11.13.
(2) 5,10 - phenanthrenequinone Pinacols knit the brows and [9,10-c] thiophene 1,3 - dicarboxylic acid (2'-ethylhexyl) ester
Synthetic route is following:
Get 0.704g (1mmol) 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, and 3-dioctyl phthalate (2 '-ethylhexyl) ester adds that pure boric acid ester of 0.762g (3mmol) di-skin, CH in 100ml single port bottle
3COOK0.6g, catalyst P dCl
2(dppf) 60mg changes argon shield, injects the anhydrous dioxane solution of 20ml with syringe, places 80 ℃ of oil baths to react 24h.Reacted cooling, reaction solution is the turbid liquid of black.The sampling limp, at sherwood oil: in the ETHYLE ACETATE=9: 1 (volume ratio), product point Rf=0.4, and blue-fluorescence is arranged.Add chloroform and fully dissolve, filter, revolve and desolventize, with sherwood oil: ETHYLE ACETATE=9: 1 (volume ratio) is elutriant, silica gel column chromatography purify the faint yellow thick semi-solid product of 0.56g, productive rate 70%.
1H?NMR(400MHz，CDCl
3，ppm)：9.095(d，2H)，8.428(dd，2H)，7.970(dd，2H)，4.395(m，4H)，1.77～1.74(m，2H)，1.37(s，24H)，1.36～1.2(m，16H)，0.971(t，6H)，0.91(t，6H).
13C?NMR(100MHz，CDCl
3，ppm)：163.811，137.533，135.111，134.165，133.11，128.502，126.493，122.802，83.945，77.33，77.012，76.694，68.67，38.761，30.473，28.936，24.952，23.842，22.962，14.03，11.056.
(3) gather (phenanthrenequione is [9,10-c] thiophene-1 also, 3-dioctyl phthalate (2 '-ethylhexyl) ester-5,10-yl)
Synthetic route is following:
Get Potassium monofluoride 47mg in polymerizing pipe, add the anhydrous NN N of 1ml, change argon gas three times, 110 ℃ of reaction 10mins make its complexing, cooling.Quick Add 5,10 - dibromo-phenanthrene quinone and [9,10-c] thiophene 1,3 - dicarboxylic acid (2'-ethylhexyl) ester and 5,10 - phenanthrenequinone and knit the brows Pinacols [9,10 -c] thiophene 1,3 - dicarboxylic acid (2'-ethylhexyl) ester of 0.1mmol, Snap triphenylphosphine palladium catalyst (Pd (PPh
3 )
4 ) 3mg, changed after the injection of argon toluene 2ml, 110 ℃ reaction 48h, system for the orange-red.Get 10mg boric acid ester monomer and be dissolved in the 1ml toluene and inject reaction system reaction 12h, and then in reaction system, inject the 1ml bromobenzene, react 12h.Get darker red orange's liquid, and have solid to separate out.Reaction system is splashed in the mixed system of 40ml absolute ethyl alcohol and 20ml water and precipitate, stir 0.5h.Filter also vacuum-drying and get the black solid of pale brown colour cast.Get the gained solid and add 20mg TMT, filter also with 50ml acetone backflow 24h.The gained filter cake is crossed post with the toluene dissolving and with Kiselgel A.Revolve and desolventize, splash in the 40ml absolute ethyl alcohol with about 2ml monochloro methane dissolved solids product and precipitate, filtration drying gets the pale brown look solid of 35mg.
Embodiment 2
(1) 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, the preparation of 3-dioctyl phthalate (2 '-ethylhexyl) ester
Synthetic route is following:
Get 250ml single port bottle I and connect constant pressure funnel and change nitrogen protection, add 1.68g t-BuOK rapidly, inject 10ml methyl alcohol with syringe then, exothermic dissolution is put into cryosel with single port bottle I after the cooling and is bathed and stir.Other gets 250ml single port bottle, takes by weighing 1.09g 2, and 7-dibromo phenanthrenequione adds 60ml benzene, is heated to and stirs fully dissolving about 70 ℃.Be cooled to 40 ℃, with 0.54g thiodiglycolic acid methyl esters, add among the above-mentioned single port bottle I, reaction solution becomes blue or green brown at once, removes cryosel bath nature and is warming up to stirring at room reaction 5d.
Stopped reaction behind the 5d, reaction solution are pale brown look turbid liquid.Aftertreatment is following: in reaction flask, add about 100ml water, stir, revolve except that organic solution, filter out undissolved solid; In filtrating, splash into HCl solution then, stir, have a large amount of yellow solid to separate out, continuing to drip HCl no longer increases to solids; Place 60 ℃ of oil baths to continue to stir 2h it is fully reacted, last suction filtration gets yellow solid, the dry product 1.30g 5 that gets; 10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, the 3-dioctyl phthalate.
With above-mentioned 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, and 3-dioctyl phthalate crude product joins in the 100ml single port bottle, adds 2 DMF, adds 8mlSOCl again
2, connecing prolong and drying tube and be heated to 80 ℃ of stirring reaction 6h, solids is dissolved as the reddish-brown clear liquor very soon.React decompression and extracted unnecessary SOCl
2Get pale brown look solid.In solids, add the 10ml bromooctane then rapidly, be warming up to 100 ℃ and continue stirring reaction 2h, this moment, reaction solution became the brown clear liquid.Reacted decompression and extracted unnecessary bromooctane, then with sherwood oil: ETHYLE ACETATE=20: 1 (volume ratio) is elutriant, and silica gel column chromatography purified product, recrystallizing methanol get 0.89g faint yellow solid thing, and this two steps productive rate together is 40%.
(2) 5,10 - phenanthrenequinone Pinacols knit the brows and [9,10-c] thiophene 1,3 - dicarboxylic acid octyl ester
Synthetic route is following:
Get 0.704g (1mmol) 5,10-dibromo phenanthrenequione is [9,10-c] thiophene-1 also, and 3-dioctyl phthalate octyl group ester adds that pure boric acid ester of 0.762g (3mmol) di-skin, CH in 100ml single port bottle
3COOK0.6g, catalyst P dCl
2(dppf) 60mg changes argon shield, injects the anhydrous dioxane solution of 20ml with syringe, places 80 ℃ of oil baths to react 24h.Reacted cooling, reaction solution is the turbid liquid of black.The sampling limp, at sherwood oil: ETHYLE ACETATE=in 9: 1, product point Rf=0.4, and blue-fluorescence is arranged.Add chloroform and fully dissolve, filter, revolve and desolventize, with sherwood oil: ETHYLE ACETATE=9: 1 is elutriant, silica gel column chromatography purify the faint yellow thick semi-solid product of 0.55g, productive rate 73%.
(3) gather (phenanthrenequione is [9,10-c] thiophene-1 also, 3-dioctyl phthalate octyl group ester-5,10-yl) ester
Synthetic route is following:
Get Potassium monofluoride 47mg in polymerizing pipe, add the anhydrous NN N of 1ml, change argon gas three times, 110 ℃ of reaction 10mins make its complexing, cooling.Quick Add 5,10 - dibromo-phenanthrene quinone and [9,10-c] thiophene 1,3 - dimethyl octyl ester and 5,10 - phenanthrenequinone Pinacols knit the brows and [9,10-c] thiophene-1, 3 - octyl dimethyl each 0.1mmol, Snap triphenylphosphine palladium catalyst (Pd (PPh
3 )
4 ) 3mg, changed after the injection of argon toluene 2ml, 110 ℃ reaction 48h, system for the orange-red.Get 10mg boric acid ester monomer and be dissolved in the 1ml toluene and inject reaction system reaction 12h, and then in reaction system, inject the 1ml bromobenzene, react 12h.Get darker red orange's liquid, and have solid to separate out.Reaction system is splashed in the mixed system of 40ml absolute ethyl alcohol and 20ml water and precipitate, stir 0.5h.Filter also vacuum-drying and get the black solid of pale brown colour cast.Get the gained solid and add 20mg TMT, filter also with 50ml acetone backflow 24h.The gained filter cake is crossed post with the toluene dissolving and with Kiselgel A.Revolve and desolventize, splash in the 40ml absolute ethyl alcohol with about 2ml methylene dichloride dissolved solids product and precipitate, filtration drying gets the pale brown look solid of 38mg.
Claims (7)
1. soluble poly 5, and 10-phenanthro-thiophene is characterized in that, has following structure:
Wherein, R is an alkyl chain; N is >=1 integer.
2. soluble poly 5 according to claim 1,10-phenanthro-thiophene is characterized in that, said R is the long-chain of C6～C20.
3. soluble poly 5 according to claim 2,10-phenanthro-thiophene is characterized in that, said R is a kind of in the structure:
C
6H
13、C
8H
17、C
10H
21、C
12H
25、C
16H
33。
4. soluble poly 5 according to claim 3,10-phenanthro-thiophene is characterized in that, said R is a kind of in the structure:
5. according to any said soluble poly 5 of claim 1～4, the preparation method of 10-phenanthro-thiophene is characterized in that, with 2,7-dibromo phenanthrenequione and the reaction of thiodiglycolic acid methyl esters obtain 5,10-dibromo phenanthro-thiophene; Again with 5,10-dibromo phenanthro-thiophene is converted into corresponding boric acid ester through the Miyaura reaction, and with 5,10-dibromo phenanthro-thiophene and its boric acid ester carry out polyreaction, obtain gathering 5,10-phenanthro-thiophene.
6. preparation method according to claim 5 is characterized in that, and is said 5, and 10-phenanthro-thiophene is through Suzuki or the polymerization of Yamamoto method.
7. any said soluble poly 5 of claim 1～4, the application of 10-phenanthro-thiophene is characterized in that, said soluble poly 5,10-phenanthro-thiophene is applied to electroluminescent, photovoltaic cell, nonlinear optics and sensory field.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351468A (en) * | 1963-01-19 | 1967-11-07 | Ciba Ltd | Thiophene compounds used as color couplers for magenta dyestuffs |
| SU425909A1 (en) * | 1972-08-24 | 1974-04-30 | Р. О. Кочкан С. Н. Баранов , Г. И. Белова | METHOD OF OBTAINING DERIVATIVE DIBENZO [th?, /] ISOTHEONPHTHENENE |
| US4797495A (en) * | 1985-11-22 | 1989-01-10 | Burroughs Wellcome Co. | Benzo[c]carbazole propanediol compound and salts thereof |
| CN1803792A (en) * | 2005-11-21 | 2006-07-19 | 中国科学院长春应用化学研究所 | Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof |
| JP2008226505A (en) * | 2007-03-09 | 2008-09-25 | Toyo Ink Mfg Co Ltd | Phenanthrothiophene based compound, its usage, and its manufacturing method |
-
2012
- 2012-03-28 CN CN 201210087357 patent/CN102617834B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351468A (en) * | 1963-01-19 | 1967-11-07 | Ciba Ltd | Thiophene compounds used as color couplers for magenta dyestuffs |
| SU425909A1 (en) * | 1972-08-24 | 1974-04-30 | Р. О. Кочкан С. Н. Баранов , Г. И. Белова | METHOD OF OBTAINING DERIVATIVE DIBENZO [th?, /] ISOTHEONPHTHENENE |
| US4797495A (en) * | 1985-11-22 | 1989-01-10 | Burroughs Wellcome Co. | Benzo[c]carbazole propanediol compound and salts thereof |
| CN1803792A (en) * | 2005-11-21 | 2006-07-19 | 中国科学院长春应用化学研究所 | Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof |
| JP2008226505A (en) * | 2007-03-09 | 2008-09-25 | Toyo Ink Mfg Co Ltd | Phenanthrothiophene based compound, its usage, and its manufacturing method |
Non-Patent Citations (2)
| Title |
|---|
| 《The Journal of Organic Chemistry》 19750228 Joan E. Shields，David E. Remy and Joseph Bornstein "Phenanthro[9,10- clthiophene. Syntheses and Reactions" 第477-479页 第40卷, 第4期 * |
| JOAN E. SHIELDS，DAVID E. REMY AND JOSEPH BORNSTEIN: ""Phenanthro[9,10- clthiophene. Syntheses and Reactions"", 《THE JOURNAL OF ORGANIC CHEMISTRY》, vol. 40, no. 4, 28 February 1975 (1975-02-28), pages 477 - 479 * |
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Effective date of registration: 20170301 Address after: 510730 Guangzhou economic and Technological Development Zone, Guangdong Shawan street, No. two, room 13, No. 614, room 15 Patentee after: Guangzhou sword photoelectric Mstar Technology Ltd Address before: 510640 Tianhe District, Guangdong, No. five road, No. 381, Patentee before: South China University of Technology |