CN102491881A - Dibromo anthracene compound and preparation method and application thereof - Google Patents

Dibromo anthracene compound and preparation method and application thereof Download PDF

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CN102491881A
CN102491881A CN2011104102477A CN201110410247A CN102491881A CN 102491881 A CN102491881 A CN 102491881A CN 2011104102477 A CN2011104102477 A CN 2011104102477A CN 201110410247 A CN201110410247 A CN 201110410247A CN 102491881 A CN102491881 A CN 102491881A
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dibromoanthracene
anthracene
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张超智
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Nanjing University of Information Science and Technology
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Abstract

The invention provides a compound prepared by 1, 8-dibromo-4, 5-dyhyroxy-9, 10-dihydro anthracene, 1, 8-dibromo-4, 5-dyhyroxy anthracene and 1, 8-dibromo-4, 5-dialkoxy anthracene and a preparation method and application thereof. The compound prepared by planar conjugated molecules including the 1, 8-dibromo-4, the 5-dyhyroxy-9, 10-dihydro anthracene, the 1, 8- dibromo-4, the 5-dyhyroxy anthracene and the 1, 8-dibromo-4, 5-dialkoxy anthracene can be applied to electron acceptor materials of photovoltaic cells. By means of the pi-piStaking effect between electron donor materials and the electron acceptor materials, contact area of an electron donor and an electron acceptor is increased, diffusion distance of an exciter is shortened, short-circuit current, filling factor and photoelectric conversion rate of the photovoltaic cells are improved, and manufacturing cost of the photovoltaic cells is reduced.

Description

The dibromoanthracene compounds
Technical field
The present invention relates to a kind of dibromoanthracene compounds, be specifically related to a kind of compound that can be used as organic/polymer solar battery electron acceptor material (1,8-two bromo-4; 5-dihydroxyl-9; 10-dihydroanthracene, 1,8-two bromo-4,5-dihydroxy-anthracene, 1; 8-two bromo-4,5-dialkoxy anthracene).
Background technology
Now, the photovoltaic cell commodity mainly are silion cells because silicon is a kind of expensive starting material, and silicon solar cell must be fixed on glass, so that silicon solar cell has is heavy, transportation and the high shortcoming of installation cost.Therefore, development film photovoltaic cell cheap, that be prone to processing and fabricating becomes the research focus.
With respect to the silicon photovoltaic cell, organic/polymer photovoltaic cell has that cost is low, in light weight, volume is little, is prone to processing, snappiness is good, the suitable characteristics that are processed into large-area flat device.Improve optoelectronic transformation efficiency and be current organic/main problem that polymer photovoltaic cell faced.According to present power supply situation,, will have price comparison advantage and wide application market if the optoelectronic transformation efficiency of organic/polymer photovoltaic cell brings up to 10%.One of key issue that improves photoelectric conversion rate is the organic/polymer materials that designs and synthesizes excellent property.
Organic/the polymer photovoltaic cell of high optoelectronic transformation efficiency needs electron donor(ED) (Donor) and electron acceptor(EA) (Acceptor) material efficiently.In recent years, the Chinese and foreign department scholar has researched and developed the good electron donor material of some character successively, for example: Katz professor's scalariform oligopolymer, the triphenylamine derivative material of Jen professor study group; China Chinese Academy of Sciences chemistry design synthetic such as professor Li Yongfang contain the Polythiophene and the Vilaterm thiophene material of side chain, professor Bao Zhishan of Chinese Academy of Sciences's Polymer Physics and chemical National Key Laboratory designs synthetic copolymerized macromolecule and branch conjugated polymer etc.
With respect to electron donor material, electron acceptor material research is less.First-generation electron acceptor(EA) is C60 verivate and C70 verivate.For example: the design synthetic C60 of the Wudl study group verivate PCBM ([6 in St Babara branch school, University of California; 6]-and phenyl C61-butyric acid methyl ester), this compound is generally used as the electron acceptor material of organic photovoltaic battery.Chemistry professor Li Yongfang of institute of the Chinese Academy of Sciences waits electron acceptor materials such as design synthetic Indene-C60 bisadduct.S-generation electron acceptor(EA) electron acceptor material is with 9, and (9,9 '-BF) is the planar conjugate molecule of representative to 9 '-bifluorenylidene.（Brunetti,?F.?G.;?Gong,?X.;?Tong,?M.;?Heeger,?A.?J.;?Wudl,?F. ?Strain?and?Hückel?Aromaticity:?Driving?Forces?for?a?Promising?New?Generation?of?Electron?Acceptors?in?Organic?Electronics, ?Angew.?Chem.?Int.?Ed. 2010, ?49,?532?–536.）
As the photovoltaic cell material of a practicality must possess be prone to synthetic, stable in properties, cheap characteristics.Therefore, some transregional companys are explored through years of researches, are locked in electron donor material on P3HT (poly (3-hexylthiophene)) and the TBP (Tetrabenzylporphrine, four benzoporphyrins) gradually.The electron acceptor material that is complementary with P3HT is C60 or C70 verivate.At present; Transregional company (for example: MIT) through approach such as process optimizations; The photoelectric conversion rate of the photovoltaic cell that uses P3HT and PCBM to make is brought up to the level greater than 8%, applied for up to a hundred battery manufacture technology patents and compound patent.But to using TBP less as the research of electron donor material; The electron acceptor material that is complementary with TBP in theory should be the big conjugated molecule in plane, therefore design and TBP be complementary electron acceptor(EA)--the planar conjugate molecule will have the raising of the photoelectric conversion rate of this type of force urges photovoltaic cell.
Summary of the invention
The objective of the invention is the defective that exists in the photovoltaic cell electron acceptor material design in order to solve, the bromo-derivative that a kind of anthracene nucleus that is complementary with the TBP electron donor material is provided is parent is as electron acceptor material.
In order to achieve the above object, the invention provides the molecule 1 of planar conjugate, 8-two bromo-4,5-dihydroxyl-9,10-dihydroanthracene, 1,8-two bromo-4,5-dihydroxy-anthracene or 1,8-two bromo-4, the structure and the preparation method of 5-dialkoxy anthracene;
Wherein, the dibromoanthracene compounds is made up of following structural formula:
Figure 2011104102477100002DEST_PATH_IMAGE001
Or
Figure 300496DEST_PATH_IMAGE002
, wherein R=H or (CH 2) nCH 3; (n=1-5), preferred R is CH 2CH 3, CH 2CH 2CH 3, CH 2CH 2CH 2CH 3, (CH 2) 4CH 3Or (CH 2) 5CH 3
Above-mentioned dibromoanthracene compounds prepares through following steps:
Step 1: use 1,8-dihydroxyl-9,10-dihydroanthracene are raw material, N-NBS (NBS) is for bromide reagent reacts, and temperature of reaction is 25～30 ℃, and reaction solvent does N, N-N (DMF); Products therefrom is put into it that recrystallization promptly gets 1 in ethanol and the THF mixing solutions again after washing, filtration, drying, 8-two bromo-4,5-dihydroxyl-9,10-dihydroanthracene; The volume ratio of said ethanol and THF is 1:1.
Step 2: will make 1,8-two bromo-4,5-dihydroxyl-9,10-dihydroanthracene and 2,3,5, the 6-tetrachlorobenzoquinone joins in the reaction solvent, stirring and refluxing; Products therefrom recrystallization in THF promptly gets 1,8-two bromo-4,5-dihydroxy-anthracene; Said reaction solvent is chloroform or THF; When reaction solvent was chloroform, the reaction times was 1.5 hours; When reaction solvent was THF, the reaction times was 0.5 hour.
Step 3: what will make is said 1,8-two bromo-4, and 5-dihydroxy-anthracene, salt of wormwood and RBr (alkylating reagent) join N, NIn-the N, heated and stirred is reacted; The reaction products therefrom is poured in the cold water, through filter, drying, again it is put into that recrystallization promptly gets 1 in THF or the ethanol, 8-two bromo-4,5-dialkoxy anthracene; Said RBr is BrCH 2CH 3, BrCH 2CH 2CH 3, BrCH 2CH 2CH 2CH 3, Br (CH 2) 4CH 3Or Br (CH 2) 5CH 3When RBr is BrCH 2CH 3The time, temperature of reaction is 35～38 ℃, the reaction times is 96 hours; When RBr is BrCH 2CH 2CH 3The time, temperature of reaction is 65～70 ℃, the reaction times is 48 hours; When RBr is BrCH 2CH 2CH 2CH 3, Br (CH 2) 4CH 3Or Br (CH 2) 5CH 3The time, temperature of reaction is 95～100 ℃, the reaction times is 30 hours.
Above-mentioned dibromoanthracene verivate is used for the photovoltaic cell electron acceptor material; Through the π between electron donor material and electron acceptor material-π Staking effect; Increase the contact area of electron donor(ED) and acceptor; Shorten the diffusion length of exciton, improve short-circuit current, packing factor and the photoelectric conversion rate of photovoltaic cell; Reduce the cost of manufacture of photovoltaic cell.
The present invention compares prior art and has the following advantages: the present invention provides the dibromoanthracene compounds to have big conjugated system, and prepares the productive rate height through methods such as bromine replacement, alkylated reactions.Dibromoanthracene compounds of the present invention is during as the photovoltaic cell electron acceptor material; Through the π between electron acceptor material-π Staking effect; Increase the contact area of electron donor(ED) and acceptor, shorten the diffusion length of exciton, improve short-circuit current, packing factor and the photoelectric conversion rate of photovoltaic cell; Simultaneously the anthracene compounds as electron acceptor material is carried out bromine and replace, significantly improve the photoelectric coefficient of photovaltaic material.
Description of drawings
Fig. 1 is electron acceptor material 1 in the film photovoltaic cell of the present invention, 8-two bromo-4,5-dihydroxyl-9, the preparation feedback formula of 10-dihydroanthracene.
Fig. 2 is electron acceptor material 1 in the film photovoltaic cell of the present invention, 8-two bromo-4, the preparation feedback formula of 5-dihydroxy-anthracene.
Fig. 3 is electron acceptor material 1 in the film photovoltaic cell of the present invention, 8-two bromo-4, the preparation feedback formula of 5-dialkoxy anthracene.
Fig. 4 is electron acceptor material 1 in the film photovoltaic cell of the present invention, 8-two bromo-4, the abosrption spectrogram of 5-diethoxy anthracene.
Among the figure, R is CH 2CH 3, CH 2CH 2CH 3, CH 2CH 2CH 2CH 3, (CH 2) 4CH 3Or (CH 2) 5CH 3
Embodiment
Below in conjunction with accompanying drawing structure of dibromoanthracene verivate of the present invention and preparation method thereof is elaborated.
Embodiment 1
1,8-two bromo-4,5-dihydroxyl-9, the 10-dihydroanthracene is prepared from through following method, referring to Fig. 1:
One TM is housed, in the three-necked bottle of mechanical stirrer, adds 10.6 g1; 8-dihydroxyl-9,10-dihydroanthracene (compound I) and 100 mL DMF, ice-water bath is chilled to 5 ℃; Add 20.5 g NBS under stirring, controlled temperature is no more than 20 ℃ in batches, adds the back temperature and rises to stirring at room 12 hours; Be warming up to 100 ℃, stirred 0.5 hour; Then, in the impouring 100g trash ice, produce orange solids, filter; Filter cake is used hot wash, 10 mL washing with alcohol, after the drying, with V (ethanol): V (THF)=1:1 70 mL ethanol/the tetrahydrofuran solution recrystallization once; Obtain 10.8 g compound I I (1,8-two bromo-4,5-dihydroxyl-9; The 10-dihydroanthracene), be orange powder, productive rate is 58.6 ﹪.The H spectrum data of compound I I are following: 1H NMR (300 MHz, CDCl3,25 ° of C, TMS) δ=3.91 (2 H, s), 4.17 (2 H, s), 6.75 (2 H, d), 7.18 (2H, d).
Embodiment 2
1,8-two bromo-4, the 5-dihydroxy-anthracene is prepared from through following method, referring to Fig. 2:
With 3.70 g compound I I and 2.70 g 2,3,5, the 6-tetrachlorobenzoquinone joins in the chloroform; Stirring and refluxing 1.5 hours, solvent evaporated adds 50 mL hot water, filters; 10 mL washing with alcohol after the drying, with THF 34 mL recrystallizations once, obtain the compound III (1 of 2.95 g; 8-two bromo-4, the 5-dihydroxy-anthracene), being red powder, productive rate is 80.2 ﹪.The H spectrum data of compound III are following: 1H NMR (300 MHz, CDCl3,25 ° of C, TMS) δ=6.77 (2 H, d), 7.80 (2H, d), 9.26 (1 H, s), 9.38 (1 H, s).
Embodiment 3
1,8-two bromo-4,5-diethoxy anthracene is prepared from through following method, referring to Fig. 3:
Under the nitrogen protection, 2.76 g salt of wormwood, 1.84 g compound III, 3.67 g monobromethanes and 20 mL DMF are joined in the 100 mL four-necked bottles, 35～38 ℃ of controlled temperature stirred 96 hours.After reaction mixture temperature is reduced to room temperature, be poured in the 50 g ice, filter 20 mL * 3 distilled water washs; After the drying, with THF 18 mL recrystallizations once, obtain the compound 1 of 1.89 g, 8-two bromo-4; 5-diethoxy anthracene is red powder, and productive rate is 90.9 ﹪.Compound 1,8-two bromo-4, the H spectrum data of 5-diethoxy anthracene are following: 1H NMR (D 3CCOCD 3): δ=1.33 (t, 6H), 3.98 (q, 4 H), 6.79 (d, 2 H), 7.75 (d, 2 H), 9.31 (s, 1 H), 9.43 (s, 1 H).
Embodiment four
1,8-two bromo-4,5-dipropoxy anthracene is prepared from through following method, referring to Fig. 3:
Under the nitrogen protection, 2.76 g salt of wormwood, 1.84 g compound III, 4.16 g N-PROPYLE BROMIDEs and 20 mL DMF are joined in the 100 mL four-necked bottles, 65～70 ℃ of controlled temperature stirred 48 hours.After reaction mixture temperature is reduced to room temperature, be poured in the 50 g ice, filter 20 mL * 3 distilled water washs; After the drying, with ethanol 21 mL recrystallizations once, obtain the compound 1 of 1.88 g, 8-two bromo-4; 5-dipropoxy anthracene is red powder, and productive rate is 85.5 ﹪.Compound 1,8-two bromo-4, the H spectrum data of 5-dipropoxy anthracene are following: 1H NMR (D 3CCOCD 3): δ=0.98 (t, 6H), 1.60-1.80 (m, 4H), 4.00 (t, 4 H), 6.78 (d, 2 H), 7.74 (d, 2 H), 9.33 (s, 1 H), 9.44 (s, 1 H).
Embodiment five
1,8-two bromo-4,5-dibutoxy anthracene is prepared from through following method, referring to Fig. 3:
Under the nitrogen protection, 2.76 g salt of wormwood, 1.84 g compound III, 4.65 g NBBs and 20 mL DMF are joined in the 100 mL four-necked bottles, 95～100 ℃ of controlled temperature stirred 30 hours.After reaction mixture temperature is reduced to room temperature, be poured in the 50 g ice, filter 20 mL * 3 distilled water washs; After the drying, with ethanol 20 mL recrystallizations once, obtain the compound 1 of 2.03 g, 8-two bromo-4; 5-dibutoxy anthracene is red powder, and productive rate is 86.8 ﹪.Compound 1,8-two bromo-4, the H spectrum data of 5-dibutoxy anthracene are following: 1H NMR (D 3CCOCD 3): δ=0.96 (t, 6H), 1.35-1.80 (m, 8H), 3.98 (t, 4 H), 6.78 (d, 2 H), 7.75 (d, 2 H), 9.31 (s, 1 H), 9.42 (s, 1 H).
Embodiment six
1,8-two bromo-4,5-two pentyloxy anthracenes are prepared from through following method, referring to Fig. 3:
Under the nitrogen protection, 2.76 g salt of wormwood, 1.51 g compound III, 5.14 g bromo pentane silanes and 20 mL DMF are joined in the 100 mL four-necked bottles, 95～100 ℃ of controlled temperature stirred 30 hours.After reaction mixture temperature is reduced to room temperature, be poured in the 50 g ice, filter 20 mL * 3 distilled water washs; After the drying, with ethanol 20 mL recrystallizations once, obtain the compound 1 of 1.88 g, 8-two bromo-4; 5-two pentyloxy anthracenes are red powder, and productive rate is 85.1 ﹪.1,8-two bromo-4, the H spectrum data of 5-two pentyloxy anthracenes are following: 1H NMR (D 3CCOCD 3): δ=0.98 (t, 6H), 1.30-1.82 (m, 16H), 3.99 (t, 4 H), 6.80 (d, 2 H), 7.77 (d, 2 H), 9.34 (s, 1 H), 9.46 (s, 1 H).
Embodiment seven
1,8-two bromo-4,5-two hexyloxy anthracenes are prepared from through following method, referring to Fig. 3:
Under the nitrogen protection, 2.76 g salt of wormwood, 1.84 g compound III, 5.63 g bromohexanes and 20 mL DMF are joined in the 100 mL four-necked bottles, 95～100 ℃ of controlled temperature stirred 30 hours.After reaction mixture temperature is reduced to room temperature, be poured in the 50 g ice, filter 20 mL * 3 distilled water washs; After the drying, with ethanol 20 mL recrystallizations once, obtain the compound 1 of 2.17 g, 8-two bromo-4; 5-two hexyloxy anthracenes are red powder, and productive rate is 81.0 ﹪.Compound 1,8-two bromo-4, the H spectrum data of 5-two hexyloxy anthracenes are following: 1H NMR (D 3CCOCD 3): δ=0.96 (t, 6H), 1.29-1.80 (m, 16H), 3.98 (t, 4 H), 6.77 (d, 2 H), 7.75 (d, 2 H), 9.31 (s, 1 H), 9.44 (s, 1 H).
Effect embodiment
Be illustrated in figure 4 as among the embodiment 31 of preparation, 8-two bromo-4, the uv absorption spectra of 5-diethoxy anthracene can know that by figure the cut-off wavelength of this compound is 610 nm; The difference of its highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy level is 2.39 eV, and just the energy level as electron acceptor material is 2.39 volts.

Claims (9)

1. the dibromoanthracene compounds is characterized in that, described dibromoanthracene compounds is made up of following structural formula:
Figure 761883DEST_PATH_IMAGE002
Or
Figure 761848DEST_PATH_IMAGE004
, wherein R=H or (CH 2) nCH 3; (n=1-5).
2. dibromoanthracene compounds according to claim 1 is characterized in that, described R is CH 2CH 3, CH 2CH 2CH 3, CH 2CH 2CH 2CH 3, (CH 2) 4CH 3Or (CH 2) 5CH 3
3. the preparation method of dibromoanthracene compounds is characterized in that, is realized by following steps:
Step 1: get 1,8-dihydroxyl-9,10-dihydroanthracene (I) and bromide reagent in molar ratio 1: (2～4) reaction, wherein the bromination temperature is 25～30 ℃, obtains 1,8-two bromo-4,5-dihydroxyl-9,10-dihydroanthracene (II); Said bromide reagent is NBS.
4. the preparation method of dibromoanthracene compounds according to claim 3 is characterized in that, and is further comprising the steps of:
Step 2: with products therefrom in the step 11,8-two bromo-4,5-dihydroxyl-9,10-dihydroanthracene (II) and 2; 3,5,6-tetrachlorobenzoquinone in molar ratio 1: (1～4) reaction joins in chloroform or the THF; Stirring and refluxing obtains 1,8-two bromo-4,5-dihydroxy-anthracene (III).
5. the preparation method of dibromoanthracene compounds according to claim 4 is characterized in that, and is further comprising the steps of:
Step 3: under nitrogen protection, with products therefrom in the step 21,8-two bromo-4; 5-dihydroxy-anthracene (III), salt of wormwood and alkylating reagent in molar ratio 1: (2～20): (2～15) reaction, join among the DMF, heated and stirred obtains 1; 8-two bromo-4,5-dialkoxy anthracene compound (IV); Said alkylating reagent is monobromethane, N-PROPYLE BROMIDE, NBB, bromo pentane silane or bromohexane.
6. the preparation method of dibromoanthracene compounds according to claim 5 is characterized in that, alkylating reagent described in the step 3 is a monobromethane, and temperature of reaction is 35～38 oC, the reaction times is 96 hours.
7. the preparation method of dibromoanthracene compounds according to claim 5 is characterized in that, alkylating reagent described in the step 3 is a N-PROPYLE BROMIDE, and temperature of reaction is 65～70 oC, the reaction times is 48 hours.
8. the preparation method of dibromoanthracene compounds according to claim 5 is characterized in that, alkylating reagent described in the step 3 is NBB, bromo pentane silane or bromohexane, and temperature is 95～100 oC, the reaction times is 30 hours.
9. the dibromoanthracene compounds is as the application of photovoltaic cell acceptor material.
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CN103073387A (en) * 2013-02-08 2013-05-01 天津师范大学 Preparation method of 9, 10-dibromoanthracene
CN104211921A (en) * 2013-05-29 2014-12-17 海洋王照明科技股份有限公司 Conjugated polymer, preparation method and applications thereof
CN108689978A (en) * 2018-05-14 2018-10-23 南京信息工程大学 2- imido grpups -3-(4- nitrobenzophenones)-6-[4-(4- nitrophenylazos)Phenyl benzopyrane

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103073387A (en) * 2013-02-08 2013-05-01 天津师范大学 Preparation method of 9, 10-dibromoanthracene
CN104211921A (en) * 2013-05-29 2014-12-17 海洋王照明科技股份有限公司 Conjugated polymer, preparation method and applications thereof
CN108689978A (en) * 2018-05-14 2018-10-23 南京信息工程大学 2- imido grpups -3-(4- nitrobenzophenones)-6-[4-(4- nitrophenylazos)Phenyl benzopyrane
CN108689978B (en) * 2018-05-14 2021-11-12 南京信息工程大学 2-imino-3- (4-nitrophenyl) -6- [2- (4-nitrophenyl) azo ] benzopyran

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