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Indolo[3,2,1-jk]carbazole derivative, preparation method and application

A carbazole derivative, 1-jk technology, applied in chemical instruments and methods, photosensitive equipment, methenyl/polymethenyl dyes, etc., can solve the problems of complicated preparation process and high price

Inactive Publication Date: 2013-06-05
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since ruthenium is a rare metal, it is expensive and the preparation process is complicated

Method used

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  • Indolo[3,2,1-jk]carbazole derivative, preparation method and application
  • Indolo[3,2,1-jk]carbazole derivative, preparation method and application
  • Indolo[3,2,1-jk]carbazole derivative, preparation method and application

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preparation example Construction

[0051] (11) The preparation process of the starting material A used in the present invention can be carried out according to the following synthetic route, and the specific experimental steps can refer to the literature (Tetrahedron Letters 2012, 53(39), 5248-5252).

[0052]

Embodiment 1

[0055] Preparation of Example 1 (E)-2-cyano-3-(4-(2-indolo[3,2,1-jk]carbazolyl)phenyl)acrylic acid

[0056] 1.1) Preparation of 2-bromoindolo[3,2,1-jk]carbazole (B)

[0057]

[0058] Under the condition of avoiding light, compound A (1.17g, 4.8mmol) was dissolved in dichloromethane (50mL), silica gel (10g) was added, placed in an ice-water bath, and NBS (0.86g, 4.8mmol) was added in batches under stirring , After reacting for 1 hour, the ice bath was removed, and the reaction was continued at room temperature for 15 hours. After the reaction was completed, it was filtered with suction and spin-dried. The crude product was recrystallized twice with glacial acetic acid to obtain compound B (0.9 g) as a white solid. The yield 59%, Rf=0.36(PE), M.p.208-210°C.

[0059] 1 H NMR (CDCl 3 ,300MHz),δ:8.13(s,2H),8.06(d,J=7.8Hz,2H),7.86(d,J=7.8Hz,2H),7.57(t,J=7.3Hz,2H),7.36 (t, J=7.3Hz, 2H).

[0060] 1.2) Preparation of 4-bromobenzaldehyde dimethyl acetal (14)

[0061]

[0062...

Embodiment 2

[0076] Example 2 Preparation of (E)-2-cyano-3-(5-(2-indolo[3,2,1-jk]carbazolyl)-2-thienyl)acrylic acid (F-2)

[0077] 2.1) Preparation of 2-thiophenecarbaldehyde

[0078]

[0079] Add anhydrous DMF (9.43g, 0.129mol) and thiophene (9.28g, 0.11mol) into a three-necked flask, stir, and slowly add phosphorus oxychloride (20g, 0.13mol) under nitrogen protection and an ice-salt bath, while adding Stir, the temperature of the reaction solution is controlled within 20°C, after the dropwise addition, stir at room temperature for 1 hour, raise the temperature to 80°C to 95°C, stir and reflux for 4 hours, stop heating, cool to room temperature, add 15mL of ice water and stir vigorously, Then use sodium hydroxide (40%) solution to adjust the pH=5-6, extract three times with dichloromethane, wash the organic layer with 25mL saturated sodium carbonate solution, then wash with 25mL water, dry over anhydrous sodium sulfate, filter with suction and spin dry The solvent was separated by sil...

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Abstract

The invention discloses an indolo[3,2,1-jk]carbazole derivative, a preparation method and an application. The derivative takes the indolo[3,2,1-jk]carbazole with coplane rigid structure and good heat stability as an electron donor, quinary arylheterocyclo group or hexahydric arylheterocyclo group or quinary arylheterocyclo group and hexahydric arylheterocyclo group can be introduced for taking as pi conjugate bridge unit, cyanoacrylate is taken as an electron acceptor to obtain a series of electron push-draw type indolo[3,2,1-jk]carbazole derivative, the derivative has photoelectrochemistry performance, can prepare a photosensitizer of a dye sensitization solar energy cell, the derivative enables easy preparation and simple purification, the cost of the derivative is lower than that of the trisruthenium, and the preparation cost of the dye sensitization solar energy cell can be effectively reduced.

Description

technical field [0001] The invention relates to compounds and their preparation and application, especially an indolo[3,2,1-jk]carbazole derivative and its preparation method and application. Background technique [0002] With the continuous increase of human demand for energy and a series of problems of global warming, people urgently need to find other new alternative energy sources. Dye-sensitized solar cells (B.O’Regan, M.Gratzel, Nature, 1991, 353, 737-740), as the third generation of solar cells, are expected to accelerate the conversion of renewable energy due to their low cost and environmental friendliness. [0003] Dye-sensitized Solar Cell (DSSC) has a relatively simple structure, mainly composed of porous nanocrystalline oxide semiconductor film, dye sensitizer, redox electrolyte and platinum counter electrode. The most commonly used porous nanocrystalline oxide semiconductor film is nanocrystalline TiO 2 The function of the thin film is to collect the photoele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C09B23/14C09B23/04H01G9/042H01G9/20
CPCY02E10/542
Inventor 刘乾才邓士明吕钧李君艳黄晓霞朱敏张俊彭晖闭伟新
Owner EAST CHINA NORMAL UNIV
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