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Dye based on dibenzothiophene derivative as well as synthesis method and application thereof

A technology of benzene derivatives and dithiophene, applied in the field of dyes and their synthesis based on dithienoacene derivatives, can solve problems such as large-scale industrialization restrictions and the like

Inactive Publication Date: 2013-09-25
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, expensive precious metal prices and rare precious metal resources have greatly restricted its large-scale industrialization

Method used

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  • Dye based on dibenzothiophene derivative as well as synthesis method and application thereof
  • Dye based on dibenzothiophene derivative as well as synthesis method and application thereof
  • Dye based on dibenzothiophene derivative as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the preparation of dye intermediate 1c

[0056] Under nitrogen protection, 1.97g (3.01mmol) 1a (Wang, B.; Tsang, S.-W.; Zhang, W.; Tao, Y.; Wong, M.S.Chem.Commun., 2011,47,9471 .), 1.02g (7.00mmol) 1b was dissolved in 40mL toluene, and 70mg (0.06mmol) Pd(PPh 3 ) 4 , 2.76g (20.00mmol) K 2 CO 3 , 10mL H 2 O, heated to 85°C, reacted for 15 hours, when the reaction was complete, poured the reaction system into water, extracted with dichloromethane, washed the organic phase with water several times, dried, removed the solvent, and purified by column separation to obtain 1.67g of compound 1c , yield 84%.

Embodiment 2

[0057] Embodiment 2: the preparation of dye intermediate 1d

[0058]Under nitrogen protection, dissolve 1.50g (2.27mmol) of 1c in 30mL of dichloromethane, add 0.24mL (2.58mmol) of phosphorus oxychloride, 0.28mL (3.62mmol) of N,N-dimethylformamide (DMF ), heated to 70° C. and refluxed for 8 hours. After the reaction was completed, saturated sodium acetate was added and stirred for half an hour, and the pH value of the solution was adjusted to 7 with sodium hydroxide solution. It was extracted with dichloromethane, the organic phase was washed several times with water, dried, the solvent was removed, and 1.41 g of compound 1d was obtained by column separation and purification with a yield of 90%.

Embodiment 3

[0059] Embodiment 3: the preparation of dye intermediate 1e

[0060] Under nitrogen protection, dissolve 1.29g (1.87mmol) 1d in 30mL chloroform and 10mL glacial acetic acid, add 0.40g (2.25mmol) N-bromosuccinimide (NBS), stir at room temperature for 5 hours, after the reaction , adding water to terminate the reaction, extracting with dichloromethane, washing the organic phase with sodium hydroxide solution and water several times, drying, removing the solvent, and column separation and purification to obtain 1.16 g of compound 1e, with a yield of 81%.

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Abstract

The invention belongs to the technical field of organic photoelectric materials and in particular relates to a dye based on a dibenzothiophene derivative as well as a synthesis method and application thereof. The pure organic dye provided by the invention is a type of D-A molecules taking a dibenzothiophene derivative unit as a Pi conjugate bridge or a part of Pi conjugate bridge, and the photophysical property and electrochemical property of the dye can be adjusted by partial modification of the Pi conjugate bridge. Compared with a ruthenium dye, the dye provided by the invention has the advantages that raw materials are simple in structure, low in cost, easy to obtain, sufficiently supplied and easily purified, the cost is low, the production is simple and convenient and the like. Furthermore, the dibenzothiophene derivative has favorable photoelectric property and can be applied to dye-sensitized solar cells; the service life of the battery is effectively prolonged, the voltage of an open circuit is effectively boosted, and the energy conversion efficiency can exceed 8 percent; therefore, the dye provided by the invention has a favorable development and application prospect in the field of dye-sensitized solar cells.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a dye based on dithienoacene derivatives and a synthesis method and application thereof. Background technique [0002] Dye-sensitized solar cells (DSSC) is a new type of solar cell developed based on the principle of plant chlorophyll photosynthesis, developed by Switzerland It was first proposed by the professor in 1991, so it is also called Battery. This kind of battery has a simple structure and is mainly composed of a working electrode, an electrolyte and a counter electrode. The working electrode is prepared by sintering a layer of nanoporous titanium dioxide film on a conductive glass substrate, and adsorbing a layer of photosensitive dye on the nanoporous titanium dioxide film. The electrolyte can be liquid, quasi-solid and solid, the most commonly used I 3 - / I - redox couple. The counter electrode is generally conductive glass...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01G9/042H01G9/20
CPCY02E10/542
Inventor 王忠胜冯全友周刚
Owner FUDAN UNIV
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