Synthesis and application of diethylamino coumarin dye sensitizer

A technology of coumarins and diethylamino, which is applied in the field of synthesis of diethylaminocoumarin dye sensitizers, can solve the problems that there are no literature reports on the application of solar cells, achieve good photoelectric conversion efficiency, and prepare methods simple effect

Inactive Publication Date: 2014-04-09
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

At present, there is no literature reporting

Method used

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  • Synthesis and application of diethylamino coumarin dye sensitizer
  • Synthesis and application of diethylamino coumarin dye sensitizer
  • Synthesis and application of diethylamino coumarin dye sensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] 7-Diethylamino-3-p-formylphenylcoumarin IIIa Synthesis

[0038] 3-bromo-7-diethylaminocoumarin VI (1.18 g, 4 mmol ), 4-formylphenylboronic acid VII (0.75 g, 5 mmol ) and tetrakistriphenylphosphine palladium (462 mg, 0.4 mmol ) were dissolved in dry THF 40 ml, and aqueous sodium carbonate solution (2.8 ml, 2 M ) was added. N 2 Refluxed for 8 h under protection, cooled to room temperature, and spin-dried the solvent to obtain a yellow solid (690 mg) with a yield of 54% after separation on a PE:EA=5:1 column. m.p.: 145-147 oC; 1 H NMR δ (500 MHz, CDCl 3 ): 10.03 (s, 1H, C H O), 7.93-7.89 (m, 4H, Ar-H), 7.82 (s, 1H, Ar-H), 7.35 (d, J = 8.82 Hz, 1H, Ar-H), 6.63 (dd, J = 2.38, 8.88 Hz, 1H, Ar-H), 6.53 (d, J = 2.31 Hz, 1H, Ar-H), 3.45 (q, J = 7.12 Hz, 4H, N(C H 2 CH 3 ) 2 ), 1.23 (t, J = 7.12 Hz, 6H, N(CH 2 C H 3 ) 2); HREIMS m / z 344.1156 [M+Na] + , calcd for C 20 h 19 NO 3 Na: 344.3596.

[0039] 2-cyano-3-(4-(7-(diethylamino)-cou...

Embodiment 2

[0042]

[0043] 5-(4-(7-(Diethylamino)-coumarin-3-yl)phenyl)-3-carboxymethylrhodanine IIa Synthesis

[0044] 7-Diethylamino-3-p-formylphenylcoumarin IIIa (0.032 g, 0.1 mmol) and rhodanine acetate V (0.038 g, 0.2 mmol) was dissolved in 2 ml acetonitrile and 1 ml THF, piperidine (0.001 ml, 0.01 mmol) was added, N 2 After reflux for 2 h under protection, the solvent was spin-dried, HAc:MeOH:CH 2 Cl 2 =1:5:100 column separation to obtain a red solid (33 mg), yield 67%. m.p.: > 300 oC; 1 H NMR δ (500 MHz, DMSO- d ): 8.27 (s, 1H, Ar-H), 7.96 (t, J = 8.48 Hz, 2H, Ar-H), 7.92 (s, 1H, Ar-H), 7.72 (d, J = 8.49 Hz, 2H, Ar-H), 7.54 (d, J = 8.92 Hz, 1H, Ar-H), 6.77 (dd, J = 2.26, 8.99 Hz, 1H, Ar-H), 6.59 (d, J = 2.15 Hz, 1H, Ar-H), 4.75 (s, 2H, C H 2 ), 3.47 (q, J = 7.03 Hz, 4H, N(C H 2 CH 3 ) 2 ), 1.16 (t, J = 6.98 Hz, 6H, N(CH 2 C H 3 ) 2 ); HREIMS m / z 493.0899 [M-H] - , calcd for C 25 h 21 N 2 o 5 S 2 : 493.5747.

Embodiment 3

[0046]

[0047] 4'-(7-(Diethylamino)-coumarin-3-yl)-[1,1'-biphenyl]-4-aldehyde IIIb Synthesis

[0048] 7-Diethylamino-3-p-bromophenylcoumarin VIII (1.4 g, 3.8 mmol), 4-formylphenylboronic acid VII (0.69 g , 4.6 mmol), tetrakistriphenylphosphine palladium (439 mg , 0.38 mmol) were dissolved in dry THF 40ml, and aqueous sodium carbonate solution (2.8 ml, 2 M) was added, N 2 Reflux for 8 h under protection, cool to room temperature, and spin dry the solvent. PE: EA = 5:1 After column separation, a yellow solid (500 mg, 1.26 mmol) was obtained with a yield of 33%. m.p.: 240-242 oC; 1 H NMR δ (500 MHz, CDCl 3 ): 10.08 (s, 1H, C H O), 7.98 (d, J = 8.09 Hz, 2H, Ar-H), 7.86-7.79 (m, 5H, Ar-H), 7.70 (d, J = 8.23 ​​Hz, 2H, Ar-H), 7.35 (d, J = 8.77 Hz, 1H, Ar-H), 6.63 (dd, J = 2.02, 8.82 Hz, 1H, Ar-H), 6.56 (s, 1H, Ar-H), 3.45 (q, J = 7.08 Hz, 4H, N(C H 2 CH 3 ) 2 ), 1.24 (t, J = 7.06 Hz, 6H, N(CH 2 C H 3 ) 2 ); HREIMS m / z 420.1515 [M+Na] + , calcd for ...

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Abstract

The invention discloses a diethylamino coumarin compound, and a preparation method and an application thereof. The diethylamino coumarin compound is shown as a formula (I) and a formula (II), wherein Ar is preferably selected from phenyl, phenyl and phenyl-thienyl. The diethylamino coumarin compound can be used as a dye sensitizer for a dye-sensitized solar cell and adds a novel applicable substance for selection of the dye sensitizer.

Description

technical field [0001] The invention relates to the synthesis and application of a diethylaminocoumarin dye sensitizer. Background technique [0002] Dye-sensitized solar cells (Dye Sensitized Solar Cell, DSSC) are very promising to replace silicon semiconductor photoelectric conversion components and become the next generation of practical high-performance Solar battery. Dye sensitizer is a key structural material that determines the visible light absorption and photoelectric conversion efficiency in DSSC. It has the characteristics of easy structure design, modification and processing, low cost and good stability. [0003] The research on dye sensitizers at home and abroad is mainly divided into two categories, one is organometallic complexes, and the typical structure is functional polypyridine ruthenium compounds. This kind of dye sensitizer has strong absorption in the visible light region, reversible redox performance and high oxidation stability, but the cost of rut...

Claims

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Application Information

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IPC IPC(8): C07D311/16C07D417/10C07D409/10C07D417/14C09B57/02H01G9/20
CPCY02E10/542C07D311/16C07D409/10C07D417/10C07D417/14C09B57/02H01G9/2059
Inventor 韩亮吴华彪李郁锦叶青高建荣
Owner ZHEJIANG UNIV OF TECH
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