Isodiketopyrrolopyrrole dyes and application thereof

A technology of diketo rolopyrrole and diketo rolopyrrole group is applied in the field of organic dyes and dye-sensitized solar cells to achieve the effects of easy availability of raw materials, simple synthesis method and low cost of raw materials

Active Publication Date: 2015-12-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

No pure organic dyes based on i

Method used

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  • Isodiketopyrrolopyrrole dyes and application thereof
  • Isodiketopyrrolopyrrole dyes and application thereof
  • Isodiketopyrrolopyrrole dyes and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of Dye isoDPP Containing Diketopyrrolopyrrole in π Bridge

[0046] (1) Synthesis of compound 2

[0047]

[0048] Add compound 1 (2.33g, 6.25mmol), CsCO 3 (6.11 g, 18.74 mmol) and 30 mL of dry DMF, the air in the apparatus was evacuated with a vacuum pump, and filled with Ar. The oil bath was heated to 60°C and stirred for 1 hour. A DMF (7 mL) solution of bromoisoctane (7.24 g, 37.50 mmol) was slowly injected into the above reaction solution with a disposable syringe. After the injection was completed, the temperature of the oil bath was raised to 120° C. to continue the reaction for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, and the reaction liquid was stirred by adding dilute hydrochloric acid solution to adjust the pH value of the solution to be neutral. Extract with 3×50mL dichloromethane, combine the organic phases and wash with saturated brine, dry with anhydrous sodium sulfate, remove dichlorometha...

Embodiment 2

[0066] The dye that embodiment 1 obtains carries out ultraviolet-visible absorption spectrum test, and its ultraviolet-visible absorption spectrum is as figure 1 shown. Solvent: 4-tert-butanol / acetonitrile mixed solution (v / v=1 / 1)

[0067] Concentration: 2×10 -5 m

[0068] Temperature: room temperature

[0069] Instrument: ShimadzuUV-2450 UV-Vis spectrophotometer

[0070] from figure 1 It can be seen that in the 4-tert-butanol / acetonitrile mixed solution (v / v=1 / 1), unlike most pure organic dyes, the dye isoDPP only exhibits one absorption peak, but presents a wider coverage. Over 10,000M in the 400–490nm range -1 cm -1 , which indicates that the dye has good light-harvesting ability.

Embodiment 3

[0072] The making of dye-sensitized solar cell among the present invention is as follows:

[0073] (1) Pretreatment of conductive glass (FTO): ultrasonically clean the cut FTO (2×5 cm), and rinse it with deionized water 4 times. Then soak in KOH saturated ethanol solution for 24h. Then use deionized water, acetone, deionized water and ethanol to ultrasonically clean, dry and store for later use;

[0074] (2) Preparation of photoanode: at room temperature, 15mLTi(OBu) 2 Add 50 mL of acetic acid and deionized water to the mixed solution with 20 mL of EtOH under vigorous stirring and continue to stir for 1 h. The mixture was transferred into an autoclave lined with Teflon (polytetrafluoroethylene), treated at 230° C. for 12 h, and then cooled to room temperature naturally. The resulting suspension was filtered, washed with deionized water and ethanol four times (, and dried in an oven at 50°C for 6 hours, until dry to obtain TiO 2 nanocrystalline particles. To the prepared T...

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Abstract

The invention discloses isodiketopyrrolopyrrole dyes and application thereof. According to the invention, 4,4'-dihexyloxytriphenylamine is used as an electron donor, isodiketopyrrolopyrrole is used as a Pi bridge, cyanoacetic acid is used as an electron acceptor and an anchoring group, and an alkyl chain is introduced on an isodiketopyrrolopyrrole group, so a series of purely organic dyes based on isodiketopyrrolopyrrole are synthesized. The dyes have good light-harvesting performance and large steric hindrance and hardly aggregate when adsorbing on a semiconductor membrane. The purely organic dyes with isodiketopyrrolopyrrole as the Pi bridge of electrons are applied in dye-sensitized solar cells and have good capability in inhibiting electron recombination; and the dye-sensitized solar cells have high photoelectric conversion efficiency.

Description

technical field [0001] The invention relates to the technical field of organic dyes and dye-sensitized solar cells, in particular to diketopyrrolopyrrole dyes and their applications. technical background [0002] The long-term and large-scale use of fossil energy has not only caused the increasing shortage of fossil energy and led to the depletion of fossil energy in the future, but also brought about environmental problems that are difficult to manage. Therefore, the development and utilization of sustainable clean energy such as solar energy has attracted extensive attention of scientific researchers all over the world. Among them, dye-sensitized solar cells (DSSCs) are one of the representatives of the photovoltaic industry, which has developed rapidly in the past two decades. Sensitizing dyes are an important part of the battery, which directly affects the performance and practical application of the battery, and can be divided into two categories: pure organic dyes and...

Claims

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Application Information

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IPC IPC(8): C09B23/04C09B57/00C07D487/04H01G9/20H01G9/042
CPCY02E10/542C09B57/008H01G9/2013C09B57/004H01G9/2031H01G9/2059Y02E10/549Y02P70/50H10K71/311H10K85/621H10K85/655H10K85/636H01G9/2004H01G9/2022
Inventor 曹德榕臧旭峰
Owner SOUTH CHINA UNIV OF TECH
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