Organic dye containing calixarene derivative and preparation method and application thereof

A technology of organic dyes and derivatives, applied in the field of organic dyes, to achieve the effect of improving light harvesting ability, increasing service life, and inhibiting molecular aggregation

Inactive Publication Date: 2012-08-01
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And will introduce calixarene skeleton structure unit as electron donor, cyanoacetic acid as electron acceptor, the organic dye that is connected by conjugated bridging group between electron donor and acceptor has not yet reported

Method used

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  • Organic dye containing calixarene derivative and preparation method and application thereof
  • Organic dye containing calixarene derivative and preparation method and application thereof
  • Organic dye containing calixarene derivative and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0043] Organic dyes containing calixarene derivatives. The dye uses calixarene derivatives as electron donors, cyanoacetic acid as electron acceptors, and thiophene and its derivatives as conjugated bridging groups. The organic dyes in this embodiment are referred to as R61. Its structural formula is as follows:

[0044]

[0045] See the synthetic route of organic dye R61 Figure 1 ~ Figure 3 As shown, the preparation process is as follows:

[0046] 1) Synthesis of p-tert-butyl calix[4] arene (R01)

[0047] Add 0.1 mol of p-tert-butylphenol, 3.8 mmol of sodium hydroxide and 20 mL of 37% formaldehyde solution into a 250 mL three-necked flask equipped with an oil-water separator, condenser and nitrogen protection device. Stir mechanically under nitrogen protection until dissolved ; Slowly heat to reflux state, evaporate most of the water in the oil-water separator, remove the water separator; keep stirring and reflux for 2 h at 110~120℃, then cool to room temperature, the reactant is ...

Embodiment 2

[0064] Organic dyes containing calixarene derivatives. The dye uses calixarene derivatives as electron donors, cyanoacetic acid as electron acceptors, and thiophene and its derivatives as conjugated bridging groups. The organic dyes in this embodiment are referred to as R62. Its structural formula is as follows:

[0065]

[0066] See the synthetic route of organic dye R62 Figure 1 ~ Figure 3 As shown, the preparation process is as follows:

[0067] 1) The synthesis method of compound R01, R02, R03, R04 is the same as in Example 1;

[0068] 2) Synthesis of 5,11,17,23-tetra(5'-formyldithienyl)-25,26,27,28-tetrabutoxycalix[4]arene (R52)

[0069] Add 0.2 mmol R04, 1 mmol 5'-formyl-2,2'-bithiophene-5-boronic acid, 3 mmol anhydrous potassium carbonate, 4 ml toluene and 1 ml methanol into the Schlenk bottle, stir at room temperature for about 15 minutes, and then add 0.08 mmol Pd(dppf)Cl 2 , Mix well, warm up to 100°C, react for 20 h; extract the reaction product with dichloromethane, wash...

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Abstract

The invention discloses organic dye containing calixarene derivative and a preparation method and application thereof. The organic dye has the characteristics of a classical D-pi-A structure in the organic dye, a calixarene framework and a derivative unit of the calixarene framework are introduced to serve as electron donors, and cyanoacetic acid connected with a conjugate bridge group serves as an electron acceptor and is used to prepare dye sensitized solar cells. Dye molecules are introduced to the calixarene derivative unit, thereby prolonging a conjugated chain to absorb absorption spectrum and effectively restraining molecular aggregation caused by the dye absorbed onto TiO2. In addition, the dye molecules contain a plurality of light absorption units so that the light trapping capability can be improved greatly. The organic dye serving as photosensitive dye is used for preparing the dye sensitized solar cells. The organic dye enables the service life of the cells to be prolonged through photo-thermal stability of the calixarene framework.

Description

technical field [0001] The invention belongs to the field of organic dyes, and relates to organic dyes containing calixarene derivatives, a preparation method and applications thereof. Background technique [0002] With the increasingly prominent problems of resource shortage and environmental pollution, the energy problem has become one of the focuses that need to be solved urgently in today's society. Among the many renewable resources, solar energy is undoubtedly the most ideal clean energy. The development and utilization of solar energy can effectively meet the needs of human production and life. Among solar cells, silicon solar cells occupy a dominant share in the current solar cell market due to their high conversion efficiency and mature technology, but they are difficult to popularize due to their high raw material prices and high production costs. In 1991, Professor M. Grötzel of the Swiss Federal Institute of Technology in Lausanne first proposed dye-sensitized s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06H01G9/20H01M14/00H01L51/46
CPCY02E10/542Y02E10/549
Inventor 刘军民谭礼林苏成勇徐耀维林雪连黄剑锋
Owner SUN YAT SEN UNIV
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