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A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof

An organic dye, asymmetric technology, applied in organic dyes, organic chemistry, chemical instruments and methods, etc., can solve the problems of restricting large-scale commercial production, complex synthesis of metal complexes, and high price, and achieve enhanced light harvesting efficiency , suitable energy gap and low production cost

Inactive Publication Date: 2020-02-28
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Metal complex dyes contain heavy metals, are expensive and pollute the environment
In addition, the synthesis of some metal complexes is more complex and difficult to purify
These have greatly limited its large-scale commercial production

Method used

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  • A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof
  • A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof
  • A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Asymmetric V-type Dye Molecule V1 Containing Triphenylamine π Bridge

[0030]

[0031] Under ice-water bath at 0°C, triphenylamine (4.9g, 20mmol) was dissolved in 50ml of anhydrous DMF solution, and 50mL of POCl was slowly added dropwise 3 . Under the protection of nitrogen, the mixture was slowly heated to 87° C. and then reacted for 1 h. After cooling to room temperature, the reaction mixture was poured into an ice bath and neutralized with NaOH, then extracted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. In case of concentrating the organic layer, column chromatography on silica gel with ethyl acetate-petroleum ether mixture (1:10 / v) as eluent gave white purified compound 1a. Yield 90%. 1 H NMR (500MHz, Chloroform-d) δ9.88(s,0H),7.88–7.82(m,1H),7.36–7.30(m,1H),7.30–7.20(m,4H),7.18–7.11(m ,1H).

[0032]

[0033] Compound 1a (2.73g, 10mmol), 2-aminothiophenol (1.1mL, 10mmol) and NMP (20mL) were heated...

Embodiment 2

[0043] Asymmetric V-type Dye Molecule V2 Containing Phenylcarbazole π Bridge

[0044]

[0045] Under 0°C ice-water bath, 9-phenyl-9H-carbazole (2.43 g, 10 mmol) was dissolved in 25 ml of anhydrous DMF solution, and 25 mL of POCl3 was slowly added dropwise. Under the protection of nitrogen, the mixture was slowly heated to 85° C. and reacted for 2 h. After cooling to room temperature, the reaction mixture was poured into an ice bath and neutralized with NaOH, then extracted with chloroform, and dried over anhydrous sodium sulfate. Separation and purification by silica gel column chromatography finally obtained the target product 1b, 1.788 g of a yellow solid, and the reaction yield was 55%. 1 H NMR (500MHz, Chloroform-d) δ9.88(s,0H),8.00(dd,J=7.6,1.5Hz,1H),7.96–7.90(m,1H),7.58–7.52(m,1H), 7.47–7.42 (m, 1H), 7.29–7.19 (m, 2H).

[0046]

[0047] Compound 1b (1.37g, 5mmol), 2-aminothiophenol (0.55mL, 5mmol) and NMP (10mL) were heated in an oil bath at a temperature of 110°...

Embodiment 3

[0057] Asymmetric V-type Dye Molecule V2 Containing Phenylcarbazole π Bridge

[0058]

[0059] Under 0°C ice-water bath, 9-phenyl-9H-carbazole (2.43 g, 10 mmol) was dissolved in 25 ml of anhydrous DMF solution, and 25 mL of POCl3 was slowly added dropwise. Under the protection of nitrogen, the mixture was slowly heated to 90° C. and reacted for 1.5 h. After cooling to room temperature, the reaction mixture was poured into an ice bath and neutralized with NaOH, then extracted with chloroform, and dried over anhydrous sodium sulfate. Separation and purification by silica gel column chromatography finally obtained the target product 1b, 1.788 g of a yellow solid, and the reaction yield was 55%. 1 H NMR (500MHz, Chloroform-d) δ9.88(s,0H),8.00(dd,J=7.6,1.5Hz,1H),7.96–7.90(m,1H),7.58–7.52(m,1H), 7.47–7.42 (m, 1H), 7.29–7.19 (m, 2H).

[0060]

[0061] Compound 1b (1.37g, 5mmol), 2-aminothiophenol (0.55mL, 5mmol) and NMP (10mL) were heated in an oil bath at a temperature of 12...

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Abstract

The invention discloses a class of asymmetric V-shaped organic dye sensitizers, wherein the molecules adopt triphenylamine and phenothiazine as electron donating groups, a long carbon chain is introduced into the N atom of the phenothiazine, benzothiazole is used as an auxiliary receptor, triphenylamine or phenylcarbazole is used as a pi-conjugated m-bridge, and cyanoacrylic acid is used as an anchoring group. According to the invention, benzothiazole is used as an auxiliary receptor so as to adjust energy gap and improve spectral response range, and triphenylamine or phenylcarbazole is introduced as a pi conjugate bridge so as to widen the spectral response range, so the material can move to a near infrared region, the intramolecular charge transfer is enhanced, the light capture efficiency is enhanced, the device performance is improved, and the material can be used for preparing a dye-sensitized solar cell.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a class of asymmetric V-type organic dye sensitizers and a preparation method and application thereof. Background technique [0002] Dye-sensitized solar cell (DSSC) has the advantages of simple process, low cost and environmental friendliness, and is generally considered as a solar cell technology with great development potential. At present, under the conditions of AM 1.5G radiation and 1000 lumen irradiation, the power conversion efficiency (PCE) of DSSC reaches 14.3% and 28.9% respectively, which meets the power generation requirements of large outdoor modules, showing the power generation of small modules under ambient light. Great application potential in batteries. [0003] The advantages of dye-sensitized solar cells are: (1) Compared with traditional photovoltaic technology, the investment and production costs of DSSC are p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14C09B21/00H01G9/20
CPCC07D417/12C07D417/14C09B21/00H01G9/2059Y02E10/542
Inventor 许文娟是凯航房维佳陈凯密保秀黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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