CN106279641B - A kind of benzimidazole derivative containing Phen closes the polymer-metal complex and its preparation method and application of Cu (II) - Google Patents
A kind of benzimidazole derivative containing Phen closes the polymer-metal complex and its preparation method and application of Cu (II) Download PDFInfo
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Abstract
The present invention relates to a kind of applications for making dye sensitizing agent such as polymer-metal complex of 1 benzimidazole derivative containing Phen of formula conjunction Cu (II) and preparation method thereof and in dye-sensitized solar cells with D-A '-π-A structure.The dye-sensitized molecules structure is using benzene thiophene derivative (BDTT) and benzene ethylene (PV) as electron donor (D), Phen benzimidazole derivative closes the complex of Cu (II) as auxiliary electron receptor (A '), the assistant ligand 8-hydroxyquinoline derivative of Cu (II) is used as main electron acceptor (A) as π bridge, alpha-cyanoacrylate (CA).By Yamamoto polymerization reaction, such two kinds of polymer-metal complex dye sensitizing agents PBDTT-PhenCu and PPV-PhenCu is obtained.Advantage of the invention is that having designed and prepared a new class of D-A '-π-A type polymerization Cu (II) complex dye sensitizer, photovoltaic application test result shows its photovoltaic performance (photoelectric conversion efficiency of PBDTT-PhenCu is 6.25%), low cost and good thermal stability with higher.
Description
Technical field
The present invention relates to polymer-metal complex and its preparations that a kind of benzimidazole derivative containing Phen closes Cu (II)
Method and the purposes as dye sensitizing agent in solar battery, belong to solar cell photoelectric Material Field in functional material.
Background technique
Dye-sensitized solar cells is simply polluted less with production process with abundant raw materials, low in cost, technology
Etc. advantages become most potential renewable one of the technology with clean energy resource.Dye-sensitized solar cells is imitated photosynthetic
Action principle, wherein dye sensitizing agent (abbreviation dyestuff), which carries, absorbs sunlight to generate electronics and transmit the most important of electronics
Function is the active component part for influencing the most critical of dye-sensitized solar cells photovoltaic performance.Dye sensitizing agent is from molecule
It is divided into D-A type D- π-A type D-A '-π-A type in structure, wherein D-A '-π-A type dye is recent development and most has development potentiality
Structure type enhances the spectral response of dyestuff, and make light absorption range to long wave by introducing additional auxiliary electron receptor A '
Direction is mobile；π bridge between accessory receptor and main receptor is while transmitting electronics, moreover it is possible to inhibit electronics compound and dark current
It generates；So D-A '-π-A type dye, compared with other types, it turns with better light, thermal stability and higher optical-electronic
Change efficiency.
Simultaneously quinoline imidazoles has big rigid structure to adjacent Féraud in this patent, and coordination can be carried out with many metals and forms strong match
Position key and rise draw electronic action, Phen benzimidazole derivative close Cu (II) complex be used as auxiliary electron receptor, be conducive to divide
The transfer of charge in son increases the extinction degree of dyestuff；Benzene thiophene derivative (BDTT) and benzene ethylene (PV) are very
Good donor material, and the polymer-metal complex formed has bigger pi-conjugated structure, not only contributes to polymer/metallic and matches
The hole transport and electron-transport of object are closed, and there is high stability；The assistant ligand 8-hydroxyquinoline derivative of Cu (II)
As π bridge, alpha-cyanoacrylate (CA) is used as main electron acceptor (A) and anchoring group, effectively promotes electron injection to TiO2It leads
Band increases effective transmission of charge, helps to improve dyestuff photoelectric efficiency.
By designing above, helps to obtain the good new dye of optical-electronic high conversion efficiency, stability, be dye sensitization
It is an important new direction of dye sensitizing agent development in solar battery.
Summary of the invention
The purpose of the present invention is to provide the polymer/metallic cooperations that a kind of benzimidazole derivative containing Phen closes Cu (II)
Object and preparation method thereof and the application that dye sensitizing agent is used as in dye-sensitized solar cells.It is polymerize by Yamamoto
Benzene thiophene derivative (BDTT) or benzene ethylene (PV) donor, synthesis are introduced in the ligand of Phen benzimidazole derivative
The polymer-metal complex PBDTT-PhenCu and PPV-PhenCu of two D-A '-π-A structures, and it is applied to the dye sensitization sun
Dye sensitizing agent can be done in battery.
The technical scheme is that a kind of benzimidazole derivative containing Phen closes the polymer/metallic cooperation of Cu (II)
Object, which is characterized in that the compound has D-A '-π-A structure, general formula such as formula 1:
Formula 1.
One kind have benzimidazole derivative containing Phen close Cu (II) polymer-metal complex PBDTT-PhenCu with
The preparation method of PPV-PhenCu:
(1) preparation of 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline:
By 1,10- phenanthroline -5,6- diketone, the bromo- 3- thiophenecarboxaldehyde of 2,5- bis- and ammonium acetate with molar ratio for 1: 1:
20 are added in single necked round bottom flask, in N2Under protection, with glacial acetic acid as solvent, dissolve by heating, until 100-140 DEG C, it stirs
Reflux 3-10 h is mixed, after being cooled to room temperature, mixed liquor is poured into ice water, is stirred, adjusts PH=6-8 with ammonium hydroxide.It filters, washing,
Finally in anhydrous CH3It is recrystallized in OH, obtains yellow green product 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f]
[1,10] phenanthroline；
(2) preparation of 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] phenanthroline:
In the reactor successively be added 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline with
NaH, molar ratio 1: 1.4.Under nitrogen protection, 40 DEG C are heated to, is slowly added to DMF solution, after 1-3 h, is added
Bromooctane is heated to 60-80 DEG C, and flow back 8-24 h.It is cooled to room temperature, filters, pour filtrate into distilled water, use CH3Cl3It carries out
Extraction, with anhydrous MgSO4After removing bromooctane with distillation under vacuum after drying, filtering, and with petroleum ether: methylene chloride: methanol=
5:5:1 crosses column purification, obtains white product 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] Féraud
Quinoline；
(3) preparation of copper complex PhenCu:
Take 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] that molar ratio is 1: 1 luxuriant and rich with fragrance
Sieve quinoline and 2- cyano -3-(8- oxyquinoline -5- base) acrylic acid in reactor, be solvent with tetrahydrofuran (THF), stirring makes
It is dissolved.Copper acetate is dissolved in methanol solution, is then added in reactor, is heated to reflux 8-24 h, cooling, filtering is used in combination
Anhydrous CH3OH washing, is dried to obtain copper complex PhenCu；
(4) polymer-metal complex PBDTT-PhenCu is synthetically prepared:
Take bis- [5- (the 2- ethyl hexyls of triphenylphosphine, zinc powder, bi triphenyl phosphine nickel chloride, bipyridyl, the bromo- 4,8- of 2,6- bis-
Base) thiophene -2- base] benzo [1,2-B:4,5-b] Dithiophene (BDTT) and copper complex (PhenCu) be with 2:50:10:1:10:10
Molar ratio be added in reaction flask.Plus refined DMF then.Under nitrogen protection, it is warming up to 80-95 DEG C, reacts 36-
64 h.It is cooling, pour into excessive anhydrous CH3CH2OH is filtered after standing overnight, with anhydrous CH3CH2OH is repeatedly washed
It washs, is dried to obtain and Cu (II) is closed with the benzimidazole derivative containing Phen that benzothiophene derivative (BDTT) is electron donor
Polymer-metal complex PBDTT-PhenCu；
(5) polymer-metal complex PPV-PhenCu is synthetically prepared:
Bis- [5- (2- ethylhexyl) thiophenes of the bromo- 4,8- of 2,6- bis- are replaced with the bromo- bis- octyloxy benzene (PV) of 2,5- of 1,4- bis-
Pheno -2- base] benzo [1,2-B:4,5-b] Dithiophene (BDTT), it has been synthesized with the reaction method similar with (4) with benzene ethylene (PV)
The polymer-metal complex PPV-PhenCu of Cu (II) is closed for the brown color benzimidazole derivative containing Phen of electron donor.
The purposes of the polymer-metal complex of a kind of conjunction of benzimidazole derivative containing Phen Cu (II): dye sensitization too
It is positive to be used as dye sensitizing agent in battery.
The main advantage of invention is: a kind of benzimidazole derivative containing Phen closes the polymer/metallic cooperation of Cu (II)
Object forms metallo-chelate using common B metal Cu (II) and derivative of phenanthroline, has been effectively combined organic dyestuff
The advantages of with metal-containing polymer (MCP) material, organometallic complex is polymerize, expands the big π system of complex molecule, mention
Its high carrier transport ability and stability, to help to improve incident photon-to-electron conversion efficiency；And with common B metal Cu (II)
Instead of noble ruthenium synthesized polymer metal complex dye, sensitization solar battery cost can not only be substantially reduced and can be reduced
Pollution to environment.
Detailed description of the invention
2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] Féraud of Fig. 1 embodiment of the present invention synthesis
Quinoline nucleus magnetic hydrogen spectrum (1HNMR) (400MHz, DMSO, TMS)；
2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] of Fig. 2 embodiment of the present invention synthesis
Phenanthroline nucleus magnetic hydrogen spectrum (1HNMR) (400MHz, CDCl3, TMS)；
The infrared spectroscopy of compound PhenCu, PBDTT-PhenCu and PPV-PhenCu of the synthesis of Fig. 3 embodiment of the present invention
(IR) (KBr crystal tabletting, 4000 ~ 400 cm-1)；
The thermogravimetric analysis (TGA) of the compound PBDTT-PhenCu and PPV-PhenCu of the synthesis of Fig. 4 embodiment of the present invention are bent
Line；
Ultraviolet-visible light (the UV- of the compound PBDTT-PhenCu and PPV-PhenCu of the synthesis of Fig. 5 embodiment of the present invention
Vis) absorption spectrum；
The dye sensitization of solar electricity of the compound PBDTT-PhenCu and PPV-PhenCu of the synthesis of Fig. 6 embodiment of the present invention
Pond Current density-voltage (J-V) curve；
The dye sensitization of solar electricity of the compound PBDTT-PhenCu and PPV-PhenCu of the synthesis of Fig. 7 embodiment of the present invention
Pond external quantum efficiency (IPCE) curve.
Specific embodiment
The preparation synthetic reaction mechanism of the compound of the present invention are as follows:
The present invention is described further combined with specific embodiments below.
Embodiment 1:
A kind of benzimidazole derivative containing Phen closes the polymer-metal complex PBDTT-PhenCu of Cu (II).
For one kind using benzene thiophene derivative (BDTT) as electron donor (D), Phen benzimidazole derivative closes Cu
(II) complex is auxiliary electron acceptor (A '), the degree of polymerization is x=7, the polymer-metal complex of the D-A '-π-A type of y=7
PBDTT-PhenCu, molecular structural formula such as formula 2:
Formula 2
The preparation implementation method of above-mentioned polymer-metal complex PBDTT-PhenCu:
A. the preparation of 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline: weighing 1 respectively,
0.3153 g(1.5 mol of 10- phenanthroline -5,6- diketone), 2,5- bis- bromo- 0.4859 g(1.5 mol of 3- thiophenecarboxaldehyde) and
2.3105 g(30 mol of ammonium acetate), round-bottomed flask (single port, 100 ml) are added to, are added glacial acetic acid (30 ml), are taken out true
Sky is filled with N2Gas, when being warming up to 60 DEG C, solid all dissolves, and relation reheating temperature rises to 120 DEG C, is stirred at reflux 5 h of reaction.It is cold
But to after room temperature, mixed liquor is poured into the deionized water of 100 ml ice, stirs, becomes cloudy, ammonium hydroxide is slowly added dropwise until PH is
7, yellow solid is gradually appeared in the process.Then it filters, and is washed with a large amount of deionized waters.Finally in anhydrous CH3In OH
It is recrystallized, obtains 0.4922 g of yellow green product that crystal form is flakes, yield: 71%.1H-NMR (400 MHz,
DMSO, ppm): 7.78 (s, 1H), 7.82 (q, 2H), 8.84 (d, 2H), 9.13 (d, 2H). Anal.
Calcd. for [C17H10N4Br2S]: C, 44.18; H, 2.18; S, 6.94;Found:C, 44.21; H, 2.15;
S, 6.89.
B.2- the preparation of (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] phenanthroline: 2- is weighed
0.4602 g(1.0 mmol of (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline) in the three of 100 ml
In mouth bottle, it is then rapidly added the NaH(1.4 mmol of 0.0336 g), vacuum nitrogen filling gas shielded, when temperature rises to 40 DEG C, first
The DMF (dry purification) for being placed on 17 ml of constant pressure funnel is slowly added dropwise into reaction system, there is bubble generation, about 1 h
Bubble is no longer generated afterwards, and system color becomes celadon, then bromooctane is slowly added dropwise, and after dripping off, is heated to 70 DEG C, reflux 12
h.After temperature is reduced to room temperature, filtering is poured into obtained filtrate in distilled water (about 100 ml), then use CH3Cl3Extracted
It takes, dry (anhydrous MgSO4), it then filters, rotation removes a part of solvent, then the operation being evaporated under reduced pressure, and boils off not in 120 DEG C
The bromooctane of reaction finally crosses column purification (petroleum ether: methylene chloride: methanol=5:5:1) and obtains 0.4171 g of white product, yield
It is 73%.1H-NMR (400 MHz,CDCl3, ppm): 13.72 (s, 1H), 9.26 (s, 2H), 9.09-9.11 (d,
H), 8.64-8.66 (d, 1H), 7.80 (s, 2H), 7.28 (s, 1H), 4.61(t, 2H), 1.27(m, 10H),
0.91(t, 3H). Anal. Calcd. for [C25H24Br2N4S]: C, 52.28; H, 4.56; N, 9.75, Br,
27.82; S, 5.58. Found: C, 52.36; H, 4.66; N, 9.65, S, 5.54.
C. the preparation of copper complex PhenCu: claim copper acetate [Cu (CH3COO)2•2H2O] 0.2932 g(1.1 mmol),
It is dissolved in spare in 20 ml anhydrous methanols.Weigh 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,
10] 0.5724 g(1.0 mmol of phenanthroline) and 2- cyano -3-(8- oxyquinoline -5- base) 0.2402 g(1.0 of acrylic acid
Mmol) in the there-necked flask of 100 ml, 25 ml of tetrahydrofuran (i.e. THF) is added, stirs, dissolves solid.By copper acetate
Dissolution in methyl alcohol, is slowly added dropwise, and then slowly heats until reflux, the reaction was continued 12 h.It is cooling, it then crosses and filters out
Filtrate is gone, with anhydrous CH3Washing is repeated in OH, dry, obtains 0.7192 g of brown color product PhenCu, yield: 81%.
FT-IR (KBr, 4000~400cm-1): 3426 (- OH), 2925(CH3), 2853 (CH2), 2216(C≡N), 1684
(C=O), 1119(C=N-M), 507(N-M). Anal. Calcd for [C40H38Br2SN6O5Cu]: C, 51.21%; H,
4.08%; N, 8.96%;S, 3.42%. Found: C, 51.27%; H, 4.04%; N, 8.89%, S, 3.47%.
D. the preparation of polymer-metal complex PBDTT-PhenCu: 0.1751 g(0.2 of complex PhenCu is weighed respectively
Mmol), bis- [5- (2- ethylhexyl) thiophene -2- base] benzo [1,2-B:4,5-b] Dithiophenes (BDTT) of bromo- 4, the 8- of 2,6- bis-
0.1474 g(0.2 mmol), triphenylphosphine (PPh3) 0.1045 g(0.4 mmol), 0.0650 g(1 .0 of zinc powder (Zn)
Mmol), bi triphenyl phosphine nickel chloride [Ni2(PPh3)Cl2] 0.1312 g(0.2 mmol), 0.0031 g(0.02 of bipyridyl
Mmol), it is added in the single port bottle of 50 ml, then measures the refined DMF of 10 ml, is added in above-mentioned flask.Reaction is in nitrogen
It is carried out in atmosphere, temperature is gradually given birth to 90 DEG C, 48 h are reacted.It is cooling, then reaction solution is poured onto excessive anhydrous
CH3CH2OH is filtered, the anhydrous CH of filter residue after standing overnight3CH2OH is repeatedly washed, dry, bright yellow solid, yield:
61%.FT-IR (KBr, 4000~400cm-1): 3434 (-OH), 3032 (Ar–H), 2923(CH3), 2846
(CH2), 2207 (C≡N), 1650 (C=O), 1567 (C=C), 1523 (C=N), 1106 (C–O–M), 497 (N–
M). Anal Calcd for [C74H78N56S5O5Cu]: C, 65.33%; H, 6.11%; N, 6.11%; S, 11.74%.
Found: C, 65.39%; H, 6.05%; N, 6.18%; S, 11.81%. GPC: =9.7kg/mol; =
19.6 kg/mol;n=7;PDI=2.02。
Embodiment 2:
A kind of benzimidazole derivative containing Phen closes the polymer-metal complex PPV-PhenCu of Cu (II).
With benzene ethylene (PV) for electron donor (D), benzimidazole derivative containing Phen closes Cu (II) complex and is one kind
Auxiliary electron acceptor (A '), degree of polymerization x=8, the D-A '-π-A type polymer-metal complex PPV-PhenCu of y=8, molecule knot
Structure formula such as formula 3:
Formula 3
The preparation method of above-mentioned polymer-metal complex PPV-PhenCu:
A. consistent with the synthetic method of step A in embodiment 1；
B. consistent with the synthetic method of step B in embodiment 1；
C. consistent with the synthetic method of step C in embodiment 1；
D. similar with the step D in embodiment 1, only use bromo- 2,5-, bis- octyloxy benzene (PPV), 0.0985 g of Isosorbide-5-Nitrae-two
(0.2 mmol) replaces bis- two thiophenes of [5- (2- ethylhexyl) thiophene -2- base] benzo [1,2-B:4,5-b] of bromo- 4, the 8- of 2,6- bis-
Pheno (BDTT), acquisition product are yellow solid product PPV-PhenCu, yield: 57%.FT-IR (KBr, 4000~400cm-1): 3434 (-OH), 3035 (Ar–H), 2923(CH3), 2854 (CH2), 2206 (C≡N), 1665 (C=O),
1564 (C=C), 1525 (C=N), 1107 (C–O–M), 495 (N–M). Anal Calcd for
[C46H40N6SO5Cu]: C, 64.55%; H, 5.15%; N, 9.84%; S, 3.72%. Found: C, 64.58%; H,
5.19%; N, 9.81%; S, 3.69%. GPC:=9.5 kg/mol;=15.58 kg/mol;n=8; PDI=1.64。
Embodiment 3:
The thermogravimetric curve of polymer-metal complex PBDTT-PhenCu and PPV-PhenCu dye sensitizing agent is measured respectively
(TGA).Method: Q50 thermogravimetric analyzer, N2It is tested under protection with the heating rate of 25 DEG C/min, test result such as Fig. 4.
Embodiment 4:
It is controlled and is measured by computer with 2611 SourceMeter of Computer-programmed Keithley, Solar
Simulator (Oriel, 91160-1000 91192, Perccell Technologies) is light source (500-W Xe, AM
1.5 G), battery-active electrode effective area is 0.25cm2, measure respectively with polymer-metal complex PBDTT-PhenCu and
PPV-PhenCu is the performance parameter and photoelectric conversion efficiency of the dye-sensitized solar cells of dye sensitizing agent, battery current
Density vs. voltage (J-V) curve such as Fig. 6, battery external quantum efficiency (IPCE) curve such as Fig. 7.Table first is that their photovoltaic performance and
Photoelectric conversion efficiency test result.
The photovoltaic performance parameter of one polymeric dye sensitizer of table
Claims (3)
1. the polymer-metal complex that a kind of benzimidazole derivative containing Phen closes Cu (II), which is characterized in that polymerization gold
Metal complex has D-A '-π-A structure, general formula such as formula 1:
2. one kind benzimidazole derivative containing Phen according to claim 1 closes the polymer-metal complex of Cu (II)
Preparation method:
(1) preparation of 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline:
By 1,10- phenanthroline -5,6- diketone, the bromo- 3- thiophenecarboxaldehyde of 2,5- bis- and ammonium acetate with molar ratio be 1:1:20 be added
Into single necked round bottom flask, in N2Under protection, with glacial acetic acid as solvent, dissolve by heating, until 100-140 DEG C, it is stirred at reflux
After being cooled to room temperature, mixed liquor is poured into ice water by 3-10h, stirring, is adjusted pH=6-8 with ammonium hydroxide, is filtered, washing, finally
In anhydrous CH3It is recrystallized in OH, obtains yellow green product 2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10]
Phenanthroline；
(2) preparation of 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] phenanthroline:
2- (2,5- dibromo thiophene -3- base) -1H- imidazoles [4,5-f] [1,10] phenanthroline and NaH are successively added in the reactor,
Molar ratio is 1:1.4, under nitrogen protection, is heated to 40 DEG C, is slowly added to DMF solution, after 1-3h, adds bromooctane,
It is heated to 60-80 DEG C, flow back 8-24h, is cooled to room temperature, and filters, pours filtrate into distilled water, use CHCl3It is extracted, with nothing
Water MgSO4After removing bromooctane with distillation under vacuum after drying, filtering, and with petroleum ether: methylene chloride: methanol=5:5:1 mistake
Column purification obtains white product 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] phenanthroline；
(3) preparation of copper complex PhenCu:
Take molar ratio be 1:1 2- (2,5- dibromo thiophene -3- base) -1 octyl-imidazo [4,5-f] [1,10] phenanthroline with
2- cyano -3- (8-hydroxyquinoline -5- base) acrylic acid in reactor, is solvent with tetrahydrofuran, stirs to dissolve, by vinegar
Sour copper is dissolved in methanol solution, is then added in reactor, is heated to reflux 8-24h, cooling, filtering, and with anhydrous CH3OH is washed
It washs, is dried to obtain copper complex PhenCu；
(4) polymer-metal complex PBDTT-PhenCu is synthetically prepared:
Take bis- [5- (2- ethylhexyl) thiophenes of triphenylphosphine, zinc powder, bi triphenyl phosphine nickel chloride, bipyridyl, the bromo- 4,8- of 2,6- bis-
Pheno -2- base] benzo [1,2-B:4,5-b] Dithiophene adds with copper complex PhenCu with the molar ratio of 2:50:10:1:10:10
Enter into reaction flask, then plus refined DMF is warming up to 80-95 DEG C under nitrogen protection, reacts 36-64h, and it is cooling,
Enter excessive anhydrous CH3CH2OH is filtered after standing overnight, with anhydrous CH3CH2OH is repeatedly washed, and is dried to obtain with benzene
Thiophthene derivative is that the benzimidazole derivative containing Phen of electron donor closes the polymer-metal complex PBDTT- of Cu (II)
PhenCu；
(5) polymer-metal complex PPV-PhenCu is synthetically prepared:
Bis- [5- (2- ethylhexyl) thiophene -2- base] benzene of the bromo- 4,8- of 2,6- bis- are replaced with the bromo- bis- octyloxy benzene of 2,5- of 1,4- bis-
And [1,2-B:4,5-b] Dithiophene, it has been synthesized with the reaction method similar with (4) and has been contained by the brown color of electron donor of benzene ethylene
Phen benzimidazole derivative closes the polymer-metal complex PPV-PhenCu of Cu (II).
3. one kind benzimidazole derivative containing Phen according to claim 1 closes the polymer-metal complex of Cu (II)
Purposes: it is used as dye sensitizing agent in dye-sensitized solar cells.
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| CN105294558A (en) * | 2015-11-06 | 2016-02-03 | 湘潭大学 | 2-cyano-3-(8-hydroxyquinoline-5-yl)acrylic acid, and preparation method and applications thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105294558A (en) * | 2015-11-06 | 2016-02-03 | 湘潭大学 | 2-cyano-3-(8-hydroxyquinoline-5-yl)acrylic acid, and preparation method and applications thereof |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis and Photovoltaic Properties of the Novel Dye of Branched Chain Polymeric Metal Complexes with Cyclopentadithiophene Derivatives as a Donor;YE LIU et al.;《Advances in Polymer Technology》;20151001;第36卷(第3期);21604(1-9) |
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