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 increasing service life, improving light harvesting ability, and inhibiting molecular aggregation

Inactive Publication Date: 2013-12-11
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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Embodiment 1

[0042] Organic dyes containing calixarene derivatives. The dyes use calixarene derivatives as electron donors, cyanoacetic acid as electron acceptors, and thiophene and its derivatives as conjugated bridging groups. The organic dyes of this embodiment are referred to as R61, Its structural formula is as follows:

[0043]

[0044] The synthetic route of organic dye R61 see Figure 1 ~ Figure 3 As shown, its preparation process is as follows:

[0045] 1) Synthesis of p-tert-butylcalix[4]arene (R01)

[0046] Add 0.1 mol of p-tert-butylphenol, 3.8 mmol of sodium hydroxide and 20 mL of 37% formaldehyde solution in a 250 mL three-necked flask equipped with an oil-water separator, condenser and nitrogen protection device, and mechanically stir until dissolved under nitrogen protection ; Slowly raise the temperature to the reflux state, remove most of the water in the oil-water separator and then remove the water separator; keep micro-stirring and reflux at 110-120°C for 2 hours,...

Embodiment 2

[0063] Organic dyes containing calixarene derivatives. The dyes use calixarene derivatives as electron donors, cyanoacetic acid as electron acceptors, and thiophene and its derivatives as conjugated bridging groups. The organic dyes of this embodiment are referred to as R62, Its structural formula is as follows:

[0064]

[0065] The synthetic route of organic dye R62 see Figure 1 ~ Figure 3 As shown, its preparation process is as follows:

[0066] 1) The synthetic method of compound R01, R02, R03, R04 is the same as Example 1;

[0067] 2) Synthesis of 5,11,17,23-tetrakis(5'-formyldithienyl)-25,26,27,28-tetrabutoxycalix[4]arene (R52)

[0068] 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 to the Schlenk bottle, stir at room temperature for about 15 min, then add 0.08 mmol Pd(dppf)Cl 2 , mix well, heat up to 100°C, and react for 20 h; the reaction product is extracted with dichloro...

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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 Patents(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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