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Julolidine compounds, and preparation method and application thereof

A technology of julolidine and compound is applied in the field of preparation of dye sensitizers, which can solve the problems of narrow absorption, wide absorption range and difficulty in the visible light region, and achieve the effect of good photoelectric conversion efficiency.

Inactive Publication Date: 2021-06-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pyridine carboxylate metal dye sensitizers are a kind of dye sensitizers studied earlier, but their absorption in the visible light region is narrow, which limits the photon absorption in the visible light region
Moreover, it is difficult to achieve a wide absorption range, high molar absorptivity and high carrier recombination kinetics for single dye sensitization.

Method used

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  • Julolidine compounds, and preparation method and application thereof
  • Julolidine compounds, and preparation method and application thereof
  • Julolidine compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The reaction formula of preparing the julolidine compounds shown in formula (I-1) is as follows:

[0026]

[0027] Preparation of julolidine compounds as shown in formula (I-1), comprises the following steps:

[0028] 1) Preparation of Vilsmeier reagent: under a nitrogen atmosphere, extract 5mL of anhydrous DMF into a Shrek tube, slowly add POCl dropwise in an ice bath 3 (0.5mL, 5mmol), stirred for 1h, and the preparation of the reagent was completed.

[0029] 2) Preparation of compound II: Weigh compound III (500mg, 1.7mmol) and dissolve it in 1,2-dichloroethane (5mL), inject it into the Shrek tube in step 1), and react at 90°C for 6h, and the reaction is complete Finally, the reaction solution was washed with water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After removing the solvent, the residue was purified by column chromatography (VPE:VEA=10:1) to obtain compound II, 320.0 mg of yellow powder solid , yield 59...

Embodiment 2

[0034] The reaction formula of preparing the julolidine compounds shown in formula (I-2) is as follows:

[0035]

[0036] Preparation of julolidine compounds as shown in formula (I-2), comprises the following steps:

[0037] Preparation of compound I-2: weigh compound II (128.7mg, 0.39mmol), rhodanine-3-acetic acid (224.1mg, 1.17mmol), dissolve in acetonitrile (16mL) and chloroform (8mL) and transfer to Shrek Tube, piperidine (0.3mL) was extracted and added dropwise, heated at reflux at 60°C for 12h under a nitrogen atmosphere, the reaction solution was cooled to room temperature, the solvent was removed, and the residue was passed through column chromatography (V DCM :V MeOH :V HOAc = 100:1:2) to obtain compound I-2, 137.1mg of red powder solid, yield 70%, melting point: 216-217°C.

[0038] The compound of the structure shown in the obtained formula (I-2) is carried out nuclear magnetic spectrum analysis, and the results are as follows: 1H NMR (500MHz, DMSO) δ8.01(s, 1...

Embodiment 3

[0039] Example 3 Julonidine compounds are used as co-sensitizers for ruthenium metal dyes:

[0040] Firstly, mix the julolidine compounds and ruthenium metal dye Z907 prepared in Examples 1-2 at a material ratio of 1:1, and dissolve them in CHCl with a volume ratio of 10:1. 3 In mixed solution with methanol, prepare dye sensitizer solution (concentration of compound is 3×10 -4 mol L -1 ).

[0041] Bilayer TiO prepared by screen printing 2 The nanoparticle film is used as a photoelectrode, including the following steps:

[0042] 1) First print a layer of 20nm TiO with a thickness of 12μm on the conductive glass FTO 2 Particles were calcined in a muffle furnace at 450 °C for 30 min, and then immersed in 0.04 mol L -1 Concentration of TiCl 4 Pretreatment in aqueous solution at 70 °C for 30 min to prepare double-layer TiO 2 Nanoparticle film. Then remove the bilayer TiO 2 The nanoparticle film was rinsed with water and ethanol, respectively, and dried with a hair dryer. ...

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Abstract

The invention discloses julolidine compounds, and a preparation method and application thereof. The chemical structural formula of the julolidine compounds is as shown in formula (I), and in the formula (I), the structural formula of a substituent R is as shown in any one of two formulas shown in the description. Two julolidine compounds are synthesized by taking julolidine as a donor and cyanoacetic acid or rhodanine acetic acid as an acceptor. After the compounds and a ruthenium metal dye Z907 are co-sensitized, an assembled dye-sensitized solar cell has good photoelectric conversion efficiency, and a new applicable substance is added for screening of a co-sensitizer of the ruthenium metal dye Z907.

Description

technical field [0001] The invention belongs to the technical field of preparation of dye sensitizers, in particular to julolidine compounds and their preparation methods and applications. Background technique [0002] Dye Sensitized Solar Cell (DSSC) has attracted much attention due to its advantages of low-cost production, easy fabrication and high photoelectric conversion efficiency. Dye sensitizer is an important part of DSSC, and its light absorption performance and energy level directly determine the photovoltaic performance of DSSC. Pyridine carboxylate metal dye sensitizers are a kind of dye sensitizers studied earlier, but their absorption in the visible light region is narrow, which limits the photon absorption in the visible light region. Moreover, it is difficult to achieve a wide absorption range, high molar absorptivity, and high carrier recombination kinetics for single dye sensitization. In order to overcome the above shortcomings and improve the photoelect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/04C09B23/04H01G9/20
CPCC07D455/04C09B23/0058C09B23/04H01G9/2063Y02E10/542
Inventor 韩亮戴申斌李郁锦叶青崔艳红
Owner ZHEJIANG UNIV OF TECH
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