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Carbazole compound and application thereof

A compound and carbazole technology, applied in the field of organic compounds, can solve the problems of narrow absorption spectrum, waste of solar energy, and limited application of carbazole organic molecules.

Active Publication Date: 2018-03-06
HEBEI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still an important defect in the existing carbazole compounds: the compound has a narrow absorption spectrum, which leads to its weak light-harvesting ability as a sensitizer for dye-sensitized solar cells, which wastes a lot of solar energy.
This problem directly affects the performance of carbazole-based organic molecules in the above-mentioned devices, and largely limits the application of carbazole-based organic molecules in the above-mentioned devices.

Method used

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  • Carbazole compound and application thereof
  • Carbazole compound and application thereof
  • Carbazole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 is synthesized (R 1 =R 2 =CH 3 , R 3 = benzene ring)

[0028]

[0029] In a 100mL one-mouth bottle, add 1.00g (5.99mmol) carbazole, dissolve it with tetrahydrofuran, place the one-mouth bottle in an ice bath and avoid light, then dissolve 2.67g (15mmol) NBS with tetrahydrofuran and pour it into constant pressure The dropping funnel was slowly dropped into a 100ml single-necked bottle, and stirred in an ice bath under the protection of nitrogen for 4 hours. The reactant was poured into 100mL water, extracted three times with ethyl acetate, the obtained liquid was spin-dried, and column chromatography was carried out with ethyl acetate:petroleum ether=1:200 to obtain 1.56g (4.8mmol) white solid, compound 2, yield 80%. 1 H NMR (500Hz, CDCl 3 ) 8.16 (s, 2H), 8.09 (s, 1H), 7.55 (d, J=8.5Hz, 2H), 7.33 (d, J=8.5Hz, 2H).

[0030]

[0031] In a 250mL single-necked bottle, add 3.35g (10.31mmol) of compound 2, 3.37g (24.76mmol) of compound 3, 5.66g (41.01...

Embodiment 2

[0044] Embodiment 2 is synthesized (R 1 =OC 8 h 17 , R 2 =CH 3 , R 3 = benzene ring)

[0045]

[0046] In a 250mL single-necked bottle, add 3.35g (10.31mmol) of compound 2, 6.19g (24.76mmol) of compound 13, 5.66g (41.01mmol) of sodium carbonate, 14ml of water, 26ml of ethanol, then add 30ml of solvent toluene, and then bubble for 30min Remove oxygen, then add 0.3g (0.26mmol) tetrakistriphenylphosphine palladium, reflux and stir at 80°C for 12h under the protection of nitrogen, add 20ml of dichloromethane after cooling, wash the organic phase with ice water 3 times, wash with anhydrous sodium sulfate After drying, the filtrate was filtered and evaporated to obtain a crude product, which was subjected to column chromatography with ethyl acetate:petroleum ether=1:200 to obtain 4.32 g (7.5 mmol) of compound 14 with a yield of 73%. 1 HNMR (500Hz, CDCl 3 )δ8.27(s,2H),8.06(s,1H),7.63(d,J=8.5Hz,6H),7.47(d,J=8.5Hz,2H),7.01(d,J=8.5Hz, 4H), 4.02(t, J=6.5Hz, 4H), 1.85-1.80(m, 4...

Embodiment 3

[0059] Embodiment 3 is synthesized (R 1 =OCH 3 , R 2 =CH 3 , R 3 = benzene ring)

[0060]

[0061] In a 250mL single-necked bottle, add 3.35g (10.31mmol) of compound 2, 3.8g (25mmol) of compound 22, 5.66g (41.01mmol) of sodium carbonate, 14ml of water, 26ml of ethanol, then add 30ml of solvent toluene, and then bubble for 30min to remove Oxygen, then add 0.3g (0.26mmol) tetrakistriphenylphosphine palladium, reflux and stir at 80°C for 12h under the protection of nitrogen, add 20ml of dichloromethane after cooling, wash the organic phase with ice water 3 times, and dry with anhydrous sodium sulfate , and then filtered and evaporated the filtrate to obtain a crude product, which was subjected to column chromatography with ethyl acetate:petroleum ether=1:200 to obtain 3.37g of compound 23 with a yield of 64%. 1 H NMR (500Hz, CDCl 3 )δ8.27(s,2H),8.06(s,1H),7.63(d,J=8.5Hz,6H),7.47(d,J=8.5Hz,2H),7.01(d,J=8.5Hz, 4H), 3.77(s, 6H).

[0062]

[0063] In a 100mL single-neck...

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Abstract

The invention discloses a carbazole compound and application thereof. The carbazole compound has a structure as shown in a formula (I) (the formula is as shown in the description; and in the formula (I), R1 is C1-C12 hydrocarbyl or C1-C12 alkoyx or C4-C20 heterocyclic radical, the heteroatom of the heterocyclic radical is N or S or O, R2 is C1-C12 hydrocarbyl, and R3 is aryl radical or heterocyclic aromatic hydrocarbon. The compound provided by the invention can serve as a sensitizing agent of a dye-sensitized solar battery.

Description

technical field [0001] The present invention relates to an organic compound and its use, in particular to a carbazole compound and its use. Background technique [0002] With the rapid development of human industrial civilization, mineral resources such as coal, oil and natural gas are increasingly depleted, and the resulting energy crisis and environmental pollution have become serious problems that need to be solved urgently. Therefore, people urgently need to find other new alternative energy sources. Organic thin-film solar cells, especially dye-sensitized solar cells, have potential practical value due to their low cost. In the above photovoltaic devices, organic molecules, as sensitizing dyes, greatly affect the performance of the devices. Carbazole compounds are widely used in the above materials due to their better optical properties and more suitable energy level structure. However, there is still an important defect in the existing carbazole compounds: the compo...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09B57/00H01G9/20H01G9/022
CPCC07D471/06C09B57/00H01G9/022H01G9/20Y02E10/542
Inventor 刘博张晓敏张凤玉王亚军
Owner HEBEI NORMAL UNIV
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