Novel redox mediators for electrolytes of photoelectrochemical solar cells

FIELD: chemistry.

SUBSTANCE: invention relates to novel redox pairs for the application in dye-sensitised solar cells DSSC. The redox pairs are formed by the general formula (bipyridine derivative)nMe(Ion)m, where the bipyridine derivative is where R2, R3 is any substituent from the group methyl, ethyl, propyl, butyl, pentyl, hexyl, Me is a metal from the group Cr, Mo, Nd, Ni, Pd, Pt, Ir, Co, Rh, Cu, W, Mn, Ta, Fe, Ru, Ion - a counterion, is any of the group ClO4-, Cl-, I-, BF4-, PF6-, CF3SO3-, n, m correspond to the metal ion valence. The novel redox pairs (version) and an electrolyte for the application on DSSC are also claimed.

EFFECT: novel redox pairs are applied in DSSC and possess the lowest redox-levels for increasing the open circuit voltage.

3 cl, 1 dwg, 1 tbl, 3 ex

 

This invention relates in General to the field of photovoltaic devices and, in particular, to the fabrication of photoelectrochemical solar cells.

The level of technology

Thin-film solar cells consisting of perkelimui meshes liquid electrolyte and covered with dye sintered titanium dioxide, has developed Dr. Michael Gratzel (Dr. Michael Gratzel) with staff at the Swiss Federal Institute of technology (Swiss Federal Institute of Technology). These photovoltaic devices refer to the General class of elements, called or photoelectrochemical dye-sensitized solar cells (SKSE). [B. O'regan and M. Gratzel, Nature, 1991, 353, 737; M. Gratzel, Nature, 2001, 414, 338.]

It is important to use dyes with maximum absorption in the visible range of the light spectrum, which allows to manufacture elements with high efficiency conversion of solar light into electrical energy (the latter the best examples showed the effectiveness of 10-11%).

Studies have shown, is used mainly in SXE redox couple (redox mediator) I-/I3-is not optimal from the point of view of the energy levels of the pair (oxidized state and a restored state) relative to the energy levels of titanium dioxide and dyes, absorbing all d�apezone the visible spectrum. It turned out that the energy of the redox level is restored I3-is higher than necessary for more effective work of SKSE, and other redox mediators with the energy of the redox level is significantly lower than in a pair of I-/I3-.

Work on the creation of such redox couples were initiated in the group of M. Graetzel (Z. Zhang, P. Chen, T. N. Murakami, S. M. Zakeeruddin and M. Graetzel, Adv. Funct. Mater., 2008, 18, 341-346) and currently have led to the creation of SKSE in the parameters, significantly exceeding SKSE based iodide redox couple. (Aswani Yella, Hsuan-Wei Lee, Hoi Nok Tsao, Chenyi Yi, Aravind Kumar Chandiran, Md. Khaja Nazeeruddin, Eric Wei-Guang Diau, Chen-Yu Yeh, Shaik M Zakeeruddin, Michael Gratzel "Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12 Percent Efficiency" // Science 2011: 629-634.)

To date, however, have not solved the problem of the maximal decrease of the energy level of the redox mediator in SCSA (increasing redox potential) to obtain SKSE with the highest values of open circuit voltage and thus the operating voltage. In this patent, we used organic ligands with pronounced acceptor ability, such as CN - substituted bipyridyl and phenanthroline - to create the redox couples on the basis of complexes with various transition metals, for which the redox level would be as low as possible energy that would create SKSE with high open-circuit voltage.

Although�Westen a number of patents: JP 2006302849 "DYE-SENSITIZED SOLAR CELL USING BLUE COPPER MODEL COMPLEX AS REDOX PAIR" and EP 1865522 "ER 1865522 "Redox pair for a dye sensitized solar cell", US 20090151779 "Redox Couples, Compositions and Uses Thereof", however, these patents do not cover the class silnoagressivnyh substituents in the redox pairs to create SKSE with high open-circuit voltage.

Summary of the invention

Claimed new redox couples for application in dye sensitized solar cells, SXE established by the General formula (derived bipyridine)n Me(Ion)m, where the derived bipyridine is:

where R1, R2, R3, any Deputy from the series methyl, ethyl, propyl, butyl, pentyl, hexyl,

Me is a metal of a series of Cr, Mo, Nd, Ni, Pd, Pt, Ir, Co, Rh, Cu, W, Mn, TA, Fe, Ru,

a Ion - counterion is any anion of a number of ClO4-, Cl-, I-, BF4-, PF6-, CF3SO3-,

n, m corresponds to the valency of the metal ion.

Claimed new redox couples for use in SKSE can be formed by the General formula (derived phenanthroline)n Me(Ion)m, where derived phenanthroline is:

where R1, R2 is any Deputy from the series methyl, ethyl, propyl, butyl, pentyl, hexyl,

Me is a metal of a series of Cr, Mo, Nd, Ni, Pd, Pt, Ir, Co, Rh, Cu, W, Mn, TA, Fe, Ru,

Ion - counterion is any anion of a number of ClO4-, Cl-, I-, BF4-, PF6-, CF3SO3-,

n, m corresponds to the valency of the metal ion.

It is stated also, the electrolyte for use in SKSE, where the main component of the electrolyte is one of the above listed compounds (i.e., compounds according to claim 1 or 2 of the claims) or a mixture of two compounds in the range of ratios from 1:100 to 100:1, and a solvent of a series of acetonitrile, isopropanol, dichlorobenzene, dimethylsulfoxide, dimethylformamide, ionic liquid-based methylimidazolium, propylimidazolium, exilimzoom and the corresponding cation, and benzimidazol.

The essence of the invention consists in the manufacture of SKSE synthesized on the basis of redox mediators with the lowest possible redox levels to increase the voltage circuit. To offset the redox levels of the complexes we chose such acceptor ligands, as biperiden and phenanthrolin, to further increase the acceptor properties of the ligands side served as Vice-CN group.

From the data cyclovoltammetry (PL. 1) we see that CN group indeed result in a shift of the redox level down (increase the redox potential) relative to the reference complexes on the basis unsubstituted bipyridinium and phenantroline ligands. Note that all the redox potentials of the substituted complexes of Table. 1 higher than that for the I-/I3-gap size 0.3 In (G. Boschloo, A. Hagfeldt Characteristics of the Iodide/Triiodide Redox Medator in Dye-Sensitized Solar Cells, Acc. Chem. Res., v. 42, 1819-1826 (2009)) (table 1).

We offer the redox compounds are soluble in most polar non-aqueous solvent, and the resulting ions (cations) is mobile enough in the solution to ensure the efficient operation of SKSE.

Made on the basis of the redox couples of SKSE really show high values of open circuit voltage (Tab. 1) and with success can replace the redox couple (I-/I3-.

Data SCSA made fairly simple methods and can be produced in large quantities this kind of elements in industrial production.

Examples

Example 1. For the manufacture of SKSE used glass TCO22 company SOLARONIX put them at the FTO electrode (subsidized fluoride the indium tin oxide). Glass was cut into glass substrates with a size of 2.5×2.5 see part of the glass substrates with FTO, which later was used for the deposition of a platinum catalyst, were drilled two holes for the subsequent pouring of the electrolyte in SKSE. All glass substrates that were used for the manufacture of SKSE, washed manually using distilled water and soda, and then washing was carried out in ultrasonic baths in three stages: first in an aqueous solution of Deconex 28 ALKA ONE with a concentration of 7 ml/l, then in distilled water and in isopropyl alcohol.The substrate, used for coating of titanium dioxide, previously immersed in an aqueous solution of TiCl4with a concentration of 50 mm and was kept in it for 20 minutes at a temperature of 70°C. After processing, the substrate is washed with distilled water and alcohol. Then, on the glass substrate with FTO deposited titanium dioxide Eurosolar P200 firms Everlight (Taiwan) knife method. Further titanium dioxide were wiped with a cotton swab soaked in isopropyl alcohol, to obtain a region with an area of 1 cm2. The resulting substrate was dried at room temperature for 10 minutes, then they were subjected to programmed heating from 30°C to 500°C for 1 hour and 45 minutes. Then, after cooling to 80°C in air, they were immersed in an aqueous solution of TiCl4with a concentration of 50 mm and was kept in it for 20 minutes at a temperature of 70°C. After the treatment with aqueous solution of TiCl4glass was maintained at a temperature of 520°C for 15 minutes. Then, after cooling to 80°C in air they sensibilizirovannoi solution of the dye d205 cartridges (Mitsubishi Paper Mills) in a mixture of CH3CH(Oh)CH3and CH3CN with a volumetric ratio of 1:1 within 24 hours. A platinum catalyst was obtained from the material Platisol company Solaronix, which was applied with a brush. It was dried at room temperature for 10 minutes before annealing at 500°C for 15 minutes. Work e�ctrad (soaked sensitizer titanium dioxide) was washed with absolute ethanol and dried by air jet. For sealing the electrodes used shrink film Meltonix thickness of 60 μm company Solaronix. For bonding the two substrates with different electrodes used homemade metal press for local thermal effects on thermal tape, so that the sensitized substrate with titanium dioxide are less heated. Exposure to heat at a temperature of 150°C was measured for 30 seconds. Then in the received cell through the drilled holes was filled with the electrolyte solution containing acetonitrile, the redox system No. 2 with concentrations 383/52.4 mm lithium perchlorate (LiClO4) with a concentration of 0.1 M pyridine with a concentration of 0.5 M So that the electrolyte does not evaporate, the holes were sealed up with shrinking film and glass with the use of a soldering iron. Current-voltage characteristics were obtained in a pilot plant, shown in Fig. 1.

From the obtained current-voltage characteristics calculated main photovoltaic parameters of the sample. The density of short circuit current of 4.7 mA/cm2the open-circuit voltage of 0.48 V, the fill factor of current-voltage characteristics of 46%, the efficiency of 1.04% (element with non-optimized structure and large surface area of 1 cm2).

Example 2. For the manufacture of SKSE used glass TCO22 company SOLARONIX put them at the FTO electrode (additional�created a fluorine indium tin oxide). Glass was cut into glass substrates with a size of 2.5×2.5 see part of the glass substrates with FTO, which later was used for the deposition of a platinum catalyst, were drilled two holes for the subsequent pouring of the electrolyte in SKSE. All glass substrates that were used for the manufacture of SKSE, washed manually using distilled water and soda, and then washing was carried out in ultrasonic baths in three stages: first in an aqueous solution of Deconex 28 ALKA ONE with a concentration of 7 ml/l, then in distilled water and in isopropyl alcohol. The substrate used for the deposition of titanium dioxide, previously immersed in an aqueous solution of TiCl4with a concentration of 50 mm and was kept in it for 20 minutes at a temperature of 70°C. After processing, the substrate is washed with distilled water and alcohol. Then, on the glass substrate with FTO deposited titanium dioxide Eurosolar P200 firms Everlight (Taiwan) knife method. Further titanium dioxide were wiped with a cotton swab soaked in isopropyl alcohol, to obtain a region with an area of 1 cm2. The resulting substrate was dried at room temperature for 10 minutes, then they were subjected to programmed heating from 30°C to 500°C for 1 hour and 45 minutes. Then, after cooling to 80°C in air, they were immersed in an aqueous solution of TiCl4with a concentration of 0 mm) and kept in it for 20 minutes at a temperature of 70°C. After treatment with aqueous solution of TiCl4glass was maintained at a temperature of 520°C for 15 minutes. Then, after cooling to 80°C in air they sensibilizirovannoi solution of the dye D131 (Mitsubishi Paper Mills) in a mixture of CH3CH(Oh)CH3and CH3CN with a volumetric ratio of 1:1 within 24 hours. A platinum catalyst was obtained from the material Platisol company Solaronix, which was applied with a brush. It was dried at room temperature for 10 minutes before annealing at 500°C for 15 minutes. Working electrode (saturated with sensitization of titanium dioxide) was washed with absolute ethanol and dried by air jet. For sealing the electrodes used shrink film Meltonix thickness of 60 μm company Solaronix. For bonding the two substrates with different electrodes used homemade metal press for local thermal effects on thermal tape, so that the sensitized substrate with titanium dioxide are less heated. Exposure to heat at a temperature of 150°C was measured for 30 seconds. Then in the received cell through the drilled holes was filled with the electrolyte solution containing acetonitrile, the redox system No. 4 with concentrations 50/28 mm, lithium perchlorate (LiClO4) with a concentration of 0.1 M pyridine with a concentration of 0.5 M So that the electrolyte does not evaporate holes bookmark�was ivalis with thermo-film, glass with the use of a soldering iron. Current-voltage characteristics were obtained in a pilot plant, shown in Fig.1.

From the obtained current-voltage characteristics to calculate the basic parameters of the sample. Short-circuit current 1.29 mA/cm2, open circuit voltage is 0.66 V, a fill factor of 50.5%, the efficiency of 0.43% (element with non-optimized structure and large surface area of 1 cm2).

Example 3. For the manufacture of SKSE used glass TCO22 company SOLARONIX coated with the electrode FTO (fluorine-doped the indium tin oxide). Glass was cut into glass substrates with a size of 2.5×2.5 see part of the glass substrates with FTO, which later was used for the deposition of a platinum catalyst, were drilled two holes for the subsequent pouring of the electrolyte in SKSE. All glass substrates that were used for the manufacture of SKSE, washed manually using distilled water and soda, and then washing was carried out in ultrasonic baths in three stages: first in an aqueous solution of Deconex 28 ALKA ONE with a concentration of 7 ml/l, then in distilled water and in isopropyl alcohol. The substrate used for the deposition of titanium dioxide, previously immersed in an aqueous solution of TiCl4with a concentration of 50 mm and was kept in it for 20 minutes at a temperature of 70�S. After processing, the substrate is washed with distilled water and alcohol. Then, on the glass substrate with FTO deposited titanium dioxide Eurosolar P200 firms Everlight (Taiwan) knife method. Further titanium dioxide were wiped with a cotton swab soaked in isopropyl alcohol, to obtain a region with an area of 1 cm2. The resulting substrate was dried at room temperature for 10 minutes, then they were subjected to programmed heating from 30°C to 500°C for 1 hour and 45 minutes. Then, after cooling to 80°C in air, they were immersed in an aqueous solution of TiCl4with a concentration of 50 mm and was kept in it for 20 minutes at a temperature of 70°C. After the treatment with aqueous solution of TiCl4glass was maintained at a temperature of 520°C for 15 minutes. Then, after cooling to 80°C in air they sensibilizirovannoi solution of the dye D131 (Mitsubishi Paper Mills) in a mixture of CH3CH(Oh)CH3and CH3CN with a volumetric ratio of 1:1 within 24 hours. A platinum catalyst was obtained from the material Platisol company Solaronix, which was applied with a brush. It was dried at room temperature for 10 minutes before annealing at 500°C for 15 minutes. Working electrode (saturated with sensitization of titanium dioxide) was washed with absolute ethanol and dried by air jet. For sealing the electrodes used shrink PL�GCC Meltonix thickness of 60 μm company Solaronix. For bonding the two substrates with different electrodes used homemade metal press for local thermal effects on thermal tape, so that the sensitized substrate with titanium dioxide are less heated. Exposure to heat at a temperature of 150°C was measured for 30 seconds. Then in the received cell through the drilled holes was filled with the electrolyte solution containing acetonitrile, the redox system No. 7 with concentrations 22/4.9 mm), lithium perchlorate (LiClO4) with a concentration of 0.1 M pyridine with a concentration of 1.2 M. the electrolyte does not evaporate, the holes were sealed up with thermo-film, glass with the use of a soldering iron. Current-voltage characteristics were obtained in a pilot plant, shown in Fig.1.

From the obtained current-voltage characteristics to calculate the basic parameters of the sample. The short-circuit current of 0.4 mA/cm2the open circuit voltage of 0.87 V, a fill factor of 26%, the efficiency of 0.09% (element with non-optimized structure and large surface area of 1 cm2).

Fig. 1 is a diagram of the setup for measuring the current-voltage characteristics of SKSE: 1 - a sample of SKSE, 2 - solar simulator with spectrum AM1.5G (Newport 96000), 3 - source-meter Characterization 2400 (Keithley), 4 - connecting cable.

1. New redox couples for application in dye sensitized solar cells, SXE formed by the General formula (derived bipyridine)nMe(Ion)m, where the derived bipyridine have:

where R1, R2, R3, any Deputy from the series methyl, ethyl, propyl, butyl, pentyl, hexyl,
Me is a metal of a series of Cr, Mo, Nd, Ni, Pd, Pt, Ir, Co, Rh, Cu, W, Mn, TA, Fe, Ru,
a Ion - counterion is any anion of a number of ClO4-, Cl-, I-, BF4-, PF6-, CF3SO3-
n, m corresponds to the valency of the metal ion.

2. New redox couples for use in SCSI formed by the General formula: (a derivative phenanthroline)nMe(Ion)m, where derived phenantroline have:

where R1, R2 is any Deputy from the series methyl, ethyl, propyl, butyl, pentyl, hexyl,
Me is a metal of a series of Cr, Mo, Nd, Ni, Pd, Pt, Ir, Co, Rh, Cu, W, Mn, TA, Fe, Ru,
Ion - counterion is any anion of a number of ClO4-, Cl-, I-, BF4-, PF6-, CF3SO3-
n, m corresponds to the valency of the metal ion.

3. The electrolyte for use in SKSE, where the main component of the electrolyte is one of the compounds according to claim 1 or 2, or a mixture of two compounds according to claims.1 and 2 in the range of ratios from 1:100 to 100:1, and t�activate the solvent from the number of acetonitrile, isopropanol, dichlorobenzene, dimethylsulfoxide, dimethylformamide, ionic liquid-based methylimidazolium, propylimidazolium, exilimzoom and the corresponding cation, and benzimidazol.



 

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13 cl, 3 dwg, 9 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing bis(3,6-di(tert-butyl)benzosemiquinolates-1,2) of cobalt (II) or manganese (II) or nickel (II), of general formula: M(SQ)2 , where: SQ is 3,6-di(tert-butyl)benzoquinolate-1,2, and M = Mn(II) or Co(II) or Ni(II). The method is characterised by that a disubstituted salt of an alkali metal salt and 3,6-di(tert-butyl) pyrocatechol-1,2 is obtained, followed by reaction thereof with 3,6-di(tert-butyl)benzoquinoline-1,2. The formed 3,6-di(tert-butyl)benzosemiquinolate-1,2 of the alkali metal reacts with a Co(II) or Mn(II) or Ni(II) halide in an inert atmosphere in tetrahydrofuran.

EFFECT: simple synthesis of bis-semiquinolates of metals.

4 cl, 5 ex

FIELD: information technology.

SUBSTANCE: article with an image includes a substrate having a masked or concealed protective image on at least part thereof, which reflects less than 50% of radiation at wavelength 800-900 nm. The protective image contains an infrared radiation absorbing compound selected from:

or salt or polymer thereof, where M is a metal selected from iron, cobalt, nickel, aluminium, scandium, chromium, vanadium, titanium, manganese and lanthanide. R1 is selected from hydrogen, phosphonate, sulphonate, nitro, halogen, cyano, thiocyano, thioalkyl, thioaryl, alkyl, alkoxy, aryl, aryloxy, amine, substituted amines and substituted aryl. One of R2 and R3 is oxygen and the other is NO; n is a number corresponding to half the coordination number of metal M; each of L and L' independently denotes a ligand which forms a complex with metal M, and y is a number which corresponds to the coordination number of metal M. The infrared radiation absorbing compound does not form an intensely coloured protective image, and the protective image is pale, colourless or tinted. The invention also discloses a method of making the article with the image, using the compound and a method of authenticating the said article.

EFFECT: obtaining a protective image which can reflect less than half the light at 800-900 nm, and a protective image which is not intensely coloured.

14 cl, 35 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel derivatives of 1-allylimidazole with metal salts , where R denotes allyl, E denotes a metal, e.g. Zn (II) or Co (II), An denotes chlorine or acetate, n equals 2.

EFFECT: novel 1-allylimidazole derivatives having antihypoxic activity are obtained.

1 cl, 7 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to chemistry of organometallic compounds, particularly to alkynyl phosphine gold-copper complexes which dissociate in a solution to form ions. The gold-copper alkynyl phosphine complexes are capable of forming covalent conjugates with proteins, thereby turning into a water-soluble form, exhibit luminescent properties and can be used as labels for fluorescence microscopy and in luminescent analysis.

EFFECT: improved properties of the compounds.

5 dwg, 4 tbl, 3 ex

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