CN109651410B - Supermolecule dye sensitizer, preparation method and application thereof - Google Patents

Supermolecule dye sensitizer, preparation method and application thereof Download PDF

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CN109651410B
CN109651410B CN201910023247.8A CN201910023247A CN109651410B CN 109651410 B CN109651410 B CN 109651410B CN 201910023247 A CN201910023247 A CN 201910023247A CN 109651410 B CN109651410 B CN 109651410B
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supramolecular
dye sensitizer
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CN109651410A (en
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贾海浪
陈宇超
纪亮
胡赛琳
秦陆丰
关明云
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Jiangsu University of Technology
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    • C—CHEMISTRY; METALLURGY
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    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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    • C—CHEMISTRY; METALLURGY
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    • C07F13/005—Compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

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Abstract

The invention belongs to the technical field of solar cells, and discloses a supramolecular dye sensitizer, a preparation method and application thereof, wherein the preparation method comprises the following steps: the supermolecule dye sensitizer is obtained by supermolecule self-assembly of metal ions by using 2,2' -dioctoconic acid as an anchoring molecule and a dicarbazole chromophore as an antenna molecule, and the supermolecule structure is shown as a formula A, so that the supermolecule sensitizer obtained by the self-assembly method has excellent photoelectric property, is simple and convenient to operate, does not need complex synthesis steps, and can adjust the spectral response capability, the charge injection performance and the like of a device by adjusting the antenna molecule, the metal ions and the anchoring molecule.
Figure DDA0001941545740000011

Description

Supermolecule dye sensitizer, preparation method and application thereof
Technical Field
The invention relates to the technical field of solar cells, in particular to a supramolecular dye sensitizer, a preparation method and application thereof.
Background
The rapid development of global economy also causes people to face two serious problems of energy crisis and environmental pollution, which become important bottlenecks of sustainable development of human society, so that many scientists are dedicated to the development of new energy, and the purposes of cleanness, recycling and the like are expected to be realized. Among numerous new energy sources, solar energy has great development potential and is one of the cleanest new energy sources available to human beings, the large-scale development of solar energy can fundamentally solve the requirements of people on energy sources, and photovoltaic power generation becomes one of the main forms of solar energy utilization.
In 1991, M of the Federal high Industrial school, Switzerland.
Figure BDA0001941545720000011
Professor has first reported dye-sensitized solar cells (Nature,1991,353, 737-. The dye-sensitized solar cell attracts the wide attention of many scientists all over the world, and is expected to become a powerful competitor of the silicon-based solar cell mainly due to the advantages of convenient manufacture, low price, high photoelectric conversion efficiency and the like. The dye-sensitized solar cell mainly comprises a nano-porous semiconductor film, a dye sensitizer, a redox electrolyte, a counter electrode, a conductive substrate and the like. Generally, a nano-porous semiconductor film is usually a metal oxide, such as TiO2, SnO2 and the like, gathered on conductive glass as a negative electrode, a counter electrode is used as a reduction catalyst, most commonly metal platinum, a dye sensitizer is adsorbed on the surface of a nano-porous titanium dioxide film, and an electrolyte containing a redox couple, such as an iodine-based electrolyte, is filled between the positive electrode and the negative electrode. Among them, dye sensitizers occupy a very important position, and largely determine the photon trapping capability and charge injection performance of devices, so the development of the sensitizers has been one of the major directions of attention of researchers. At present, the photoelectric conversion efficiency of excellent sensitizers such as N719, YD2-O-C8 and the like breaks through 13%, however, the difference from the theoretical efficiency is large, and the synthesis process of the traditional sensitizers is complex, so that the development of novel efficient dye sensitizers has good scientific significance.
Disclosure of Invention
The embodiment of the invention provides a supramolecular dye sensitizer, a preparation method and application thereof. The supermolecule sensitizer obtained by the self-assembly method has excellent photoelectric property, is simple and convenient to operate, does not need complex synthesis steps, and can adjust the spectral response capability, the charge injection performance and the like of a device by regulating and controlling antenna molecules, metal ions and anchoring molecules.
The purpose of the embodiment of the invention is realized by the following technical scheme:
in a first aspect, an embodiment of the present invention provides a preparation method of a supramolecular dye sensitizer, including the following steps: 2,2' -dicaprylic acid is used as an anchoring molecule, a dicarbazole chromophore is used as an antenna molecule, and the supramolecular dye sensitizer is obtained by performing supramolecular self-assembly on metal ions, wherein the supramolecular structure is shown as the following formula A:
Figure BDA0001941545720000021
further, the anchoring molecule structure is shown as a formula B, and the dicarbazole chromophore antenna molecule is shown as a formula C:
Figure BDA0001941545720000022
further, the metal ions are at least one of zinc, manganese, chromium, nickel and copper.
Further, the method comprises the following steps:
adding TiO into the mixture2The nano-crystal film is firstly soaked in anchoring molecule solution with certain concentration for 12-18 hours, washed and dried, then soaked in metal ion solution for 1-2 hours, then supermolecule self-assembly is carried out in antenna molecule solution for 12-18 hours, washed and dried,and then, assembling the solar cell device.
Furthermore, the solvent of the anchoring molecule is one or more of N, N-dimethylformamide, methanol and tetrahydrofuran, the solvent of the metal ion is one or more of methanol, ethanol and N, N-dimethylformamide, and the solvent of the antenna molecule is one or more of ethanol, dichloromethane, trichloromethane and tetrahydrofuran.
Furthermore, the concentration of the anchoring molecules is 0.5-2mmol, the concentration of the metal ions is 0.5-2mmol, and the concentration of the antenna molecules is 0.5-1 mmol.
In a second aspect, embodiments of the present invention provide a supramolecular dye sensitizer prepared by any one of the methods described above.
In a third aspect, an embodiment of the present invention provides an application of a supramolecular dye sensitizer in a fuel-sensitized solar cell, where the supramolecular dye sensitizer is prepared by any one of the methods described above or is the supramolecular dye sensitizer described above.
By the scheme, the supramolecular dye sensitizer, the preparation method and the application have the following beneficial effects:
the invention takes the dicarbazole modified by long carbon chain as an electron donor part, and obtains the supermolecule sensitizer of the dicarboxyl anchoring group by the coordination self-assembly of the pyridine nitrogen atoms of the antenna molecules and the anchoring molecules and metal ions. The supermolecule sensitizer obtained by the self-assembly method has excellent photoelectric property, is simple and convenient to operate, does not need complex synthesis steps, and can adjust and control antenna molecules, metal ions and anchoring molecules to adjust spectral response capability, charge injection performance and the like of a device.
Drawings
FIG. 1 is a schematic diagram illustrating the preparation of a supramolecular dye sensitizer in accordance with one embodiment of the present invention;
FIG. 2 is a J-V curve diagram of a dye-sensitized solar cell prepared by supramolecular self-assembly according to an embodiment of the present invention;
fig. 3 is an IPCE graph of a dye-sensitized solar cell prepared by supramolecular self-assembly according to an embodiment of the present invention.
Detailed Description
In order to facilitate the understanding of the scheme of the present invention for those skilled in the art, the following further describes the scheme of the present invention with reference to specific examples, and it should be understood that the examples of the present invention are illustrative of the scheme of the present invention and are not intended to limit the scope of the present invention.
In a first aspect, an embodiment of the present invention provides a preparation method of a supramolecular dye sensitizer, including the following steps: 2,2' -dicaprylic acid is used as an anchoring molecule, a dicarbazole chromophore is used as an antenna molecule, and the supramolecular dye sensitizer is obtained by performing supramolecular self-assembly on metal ions, wherein the supramolecular structure is shown as the following formula A:
Figure BDA0001941545720000041
in some embodiments of the present invention, the anchoring molecule is represented by formula B, and the dicarbazole-based chromophore antenna molecule is represented by formula C:
Figure BDA0001941545720000043
in some embodiments of the present invention, the metal ion is at least one of zinc, manganese, chromium, nickel, and copper.
In some embodiments of the invention, the method comprises the following steps:
adding TiO into the mixture2Soaking the nano-crystal film in anchoring molecular solution of certain concentration for 12-18 hr, washing, drying, soaking in metal ion solution for 1-2 hr, self-assembling supermolecule in antenna molecular solution for 12-18 hr, washing, drying, and sun dryingThe battery device can be assembled.
In some embodiments of the present invention, the solvent of the anchor molecule is one or more of N, N-dimethylformamide, methanol, and tetrahydrofuran, the solvent of the metal ion is one or more of methanol, ethanol, and N, N-dimethylformamide, and the solvent of the antenna molecule is one or more of ethanol, dichloromethane, chloroform, and tetrahydrofuran.
In some embodiments of the invention, the anchor molecule concentration is 0.5-2mmol, the metal ion concentration is 0.5-2mmol, and the antenna molecule concentration is 0.5-1 mmol.
In a second aspect, embodiments of the present invention provide a supramolecular dye sensitizer prepared by any one of the methods described above.
In a third aspect, an embodiment of the present invention provides an application of a supramolecular dye sensitizer in a fuel-sensitized solar cell, where the supramolecular dye sensitizer is prepared by any one of the methods described above or is the supramolecular dye sensitizer described above.
The invention carries out solar cell device assembly on the constructed supermolecule dye sensitizer. Punching a small hole with the diameter of about 0.8mm on the conductive glass substrate of the counter electrode for injecting electrolyte, and then injecting H2PtCl6The solution (0.02M isopropanol solution) was spin-coated on a cleaned conductive glass substrate, and sintered at high temperature to obtain a Pt counter electrode. TiO subjected to supermolecule self-assembly2And (3) packaging the electrode and the Pt counter electrode by using a 60um heat-sealing film, injecting iodine-based electrolyte in a vacuum backfill mode, and sealing the hole to obtain the DSSCs. The photoelectric conversion efficiency property of the assembled battery device was tested, and a corresponding current-voltage curve was obtained under the condition of metal zinc ions, as shown in fig. 2, the photoelectric conversion efficiency was 3.60%, and the short-circuit current density was 7.92mA cm-2The open-circuit voltage is 638mV, and the filling factor is 71.31%, which indicates that the supramolecular self-assembly method is successfully applied to the dye-sensitized solar cell.
To further confirm that 2,2' -bicinchoninic acid and antenna molecules are subjected to effective supramolecular self-assembly through metal ions, the assembled solar cell device is tested for monochromatic photoelectric conversion efficiency, and a corresponding IPCE curve is obtained, as shown in FIG. 3. As can be seen from the figure, the dye sensitizer obtained by the supermolecule self-assembly has obvious improvement on spectral response, reaches nearly 650nm, and the monochromatic photoelectric conversion efficiency of the device at 500nm reaches 37%, which also proves that the supermolecule sensitizer is successfully prepared by the invention.
The embodiment is a preparation method and application of a supramolecular sensitizer, and the preparation method specifically comprises the following steps:
(1)TiO2preparing a nanocrystalline film:
the FTO glass sheets were sonicated in deionized water solution for 30min with a detergent before use, and then washed with deionized water and ethanol. Preparation of TiO by Screen printing2Nano-crystalline photo-anode, TiO2The particle diameter is 20nm, and the pore diameter is 32 nm. The thickness of the film was 0.196cm2Of TiO22The thickness of the film was 12 μm.
(2) The preparation method of the supramolecular sensitizer comprises the following steps:
the prepared TiO is prepared according to the steps shown in FIG. 12The nanocrystalline film is firstly soaked in 1mmol of 2,2' -dioctyl-cotinamide acid in methanol solution for 18 hours, then washed by ethanol, naturally dried, then soaked in 1mmol of metal ion in methanol solution for 1 hour, then soaked in 0.5mmol of antenna molecule dicarbazole chromophore in dichloromethane solution for 8 hours, then washed by ethanol, and naturally dried.
(3) Preparing a counter electrode:
an FTO conductive glass was perforated with a hole having a diameter of about 0.8mm for electrolyte injection, and then 0.02M H was injected2PtCl6The ethanol solution is coated on the surface of the conductive glass in a spinning mode, and finally the conductive glass is sintered in a muffle furnace for half an hour at 450 ℃ and then cooled to room temperature.
(4) Preparing a dye-sensitized solar cell:
the prepared TiO is mixed with2The thin film electrode and the Pt counter electrode are bonded by a 60 mu m thin film through a hot baking gun and then injected by a vacuumizing methodIodine-based electrolyte and finally encapsulated with a thin glass slide of 0.1mm thickness.
The above are merely examples of the present application and are not intended to limit the present application. Various modifications and changes may occur to those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of the claims of the present application.

Claims (8)

1. A preparation method of a supramolecular dye sensitizer is characterized by comprising the following steps: 2,2' -dicaprylic acid is used as an anchoring molecule, a dicarbazole chromophore is used as an antenna molecule, and the supramolecular dye sensitizer is obtained by performing supramolecular self-assembly on metal ions, wherein the supramolecular structure is shown as the following formula A:
Figure DEST_PATH_IMAGE002
M=Zn2+
（A）。
2. the method for preparing a supramolecular dye sensitizer according to claim 1, wherein said anchoring molecule has a structure as shown in formula B, and said dicarbazole-based chromophore antenna molecule has a structure as shown in formula C:
Figure DEST_PATH_IMAGE004
（B）
Figure DEST_PATH_IMAGE006
（C）。
3. the method of preparing a supramolecular dye sensitizer according to claim 1, wherein said metal ion is a zinc ion.
4. The method of preparing a supramolecular dye sensitizer according to claim 1, comprising the steps of:
adding TiO into the mixture2The nano-crystal film is firstly soaked in anchoring molecule solution with certain concentration for 12-18 hours, washed and dried, then soaked in metal ion solution for 1-2 hours, then supermolecule self-assembly is carried out in antenna molecule solution for 12-18 hours, washed and dried, and then solar cell device assembly is carried out.
5. The method of claim 4, wherein the solvent for the anchor molecule is one or more selected from the group consisting of N, N-dimethylformamide, methanol, and tetrahydrofuran, the solvent for the metal ion is one or more selected from the group consisting of methanol, ethanol, and N, N-dimethylformamide, and the solvent for the antenna molecule is one or more selected from the group consisting of ethanol, dichloromethane, chloroform, and tetrahydrofuran.
6. The method of preparing a supramolecular dye sensitizer according to claim 4, wherein the concentration of anchoring molecules is 0.5-2mmol, the concentration of metal ions is 0.5-2mmol, and the concentration of antenna molecules is 0.5-1 mmol.
7. A supramolecular dye sensitizer, characterized in that said supramolecular dye sensitizer is prepared by the process according to any one of claims 1 to 6.
8. Use of a supramolecular dye sensitizer in the field of dye-sensitized solar cells, wherein said supramolecular dye sensitizer is a supramolecular dye sensitizer prepared by the preparation method of any one of claims 1 to 6 or a supramolecular dye sensitizer according to claim 7.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103539804A (en) * 2013-10-31 2014-01-29 湘潭大学 Phenothiazine-containing polymerization metal complex as well as preparation method and application thereof
CN106188506A (en) * 2016-07-22 2016-12-07 湘潭大学 One class closes polymer-metal complex dye sensitizing agent of Cu (II) and preparation method thereof containing 8 8-hydroxyquinoline derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103539804A (en) * 2013-10-31 2014-01-29 湘潭大学 Phenothiazine-containing polymerization metal complex as well as preparation method and application thereof
CN106188506A (en) * 2016-07-22 2016-12-07 湘潭大学 One class closes polymer-metal complex dye sensitizing agent of Cu (II) and preparation method thereof containing 8 8-hydroxyquinoline derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"吡啶基锚固基团染料敏化剂的合成与光伏性能研究";贾海浪等;《广东化工》;20180830;第45卷(第16期);第39,4页 *
"新型D-(π-A)2 喹喔啉类染料的制备与光伏性能研究";贾海浪等;《广东化工》;20180915;第45卷(第17期);第32,7页 *

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