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Synthesis and application of coumarin type dye sensitizer

A technology of coumarins and compounds, applied in the field of synthesis of coumarin-type dye sensitizers

Inactive Publication Date: 2013-05-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the present invention, substituted coumarin, which is readily available as a raw material, is used as a donor, thiophene is used as a bridge, and cyanoacetic acid is used as an acceptor to synthesize two coumarin-based dye sensitizer molecules with simple structures, and their photoelectric properties are investigated. At present, there is no literature reporting the solar cell application of this structure

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0037] In an ice bath and dry conditions, the POCl 3 (2 mL) was added dropwise to DMF (2 mL), stirred for half an hour to obtain Vilsmier's reagent. Dissolve 7-methoxy-3-(2’-thienyl)-coumarin (5 mmol) in DMF (15 mL), add Vilsmier reagent, and react at 60 °C for 8 h. After cooling, the reaction solution was poured into ice water (30 mL), adjusted to pH = 7 with 10% NaOH aqueous solution, and a large amount of precipitate was precipitated. Filter with suction, wash with water (30 mL×5 ), and then with a large amount of ethanol, and dry to obtain a yellow-brown solid. IIb: Yield 84.9%. Melting point 164~165 oC.

[0038] Example 3: Synthesis of 2-cyano-3-(5-(7-N,N-dimethyl-2-carbonyl-2H-benzopyran-3-yl)thiophen-2-yl)acrylic acid IIIa

example 2

[0039] Dissolve II a (2 mmol) and cyanoacetic acid (4 mmol) in acetonitrile (30 mL), add piperidine (0.5 mL), and heat to reflux for 6 h. Cool, filter with suction, and wash with acetonitrile (20 mL×3). Dry, CHCl 3 Recrystallization gave a dark red solid. IIIa: Yield 87.3 %. Melting point 282~283 oC; 1 H NMR (500 MHz, DMSO) δ: 8.67(s, 1H, C H =CCN), 8.43(s, 1H, coumarin-4- H ), 7.98 (d, J=4.3 Hz, 1H, thiophene- H ), 7.86(d, J=4.2 Hz, 1H, thiophene- H ), 7.57(d, J=9.0 Hz, 1H, Ar H ), 6.83 (dd, J=9.0, 2.3 Hz, 1H, Ar H ), 6.65(d, J=2.23 Hz, 1H, Ar H), 3.50(q, J=7.0 Hz, 4H, C H 2 CH 3 ), 1.16 (t, J=7.0 Hz, 6H, CH 2 C H 3 ); HR-ESI-MS for C 21 h 17 N 2 o 4 S: Found: 393.0927 [M-H] - ; Calcd. 393.0909.

[0040] Example 4: Synthesis of 2-cyano-3-(5-(7-methoxy-2-carbonyl-2H-benzopyran-3-yl)thiophen-2-yl)acrylic acid IIIb

example 3

[0041] Dissolve II b (2 mmol) and cyanoacetic acid (4 mmol) in acetonitrile (30 mL), add piperidine (0.5 mL), and heat at reflux for 6 h. Cool, filter with suction, and wash with acetonitrile (20 mL×3). Dry, CHCl 3 Recrystallization gave a dark red solid. IIIb: Yield 75.6%. Melting point > 300 oC; 1 H NMR (500 MHz, DMSO): δ 8.83 (s, 1H, C H =CCN ), 8.45 (s, 1H, coumarin-4- H ), 8.01~7.97(m, 2H, thiophene- H ), 7.77 (d, J = 8.7 Hz, 1H, Ar H ), 7.15 (s, 1H, Ar H ), 7.07 (d, J = 8.7, 1H, Ar H ), 3.91 (s, 3H, OC H 3 ); HR-ESI-MS for C 18 h 10 NO 5 S: Found: 352.0293 [M-H] - ; Calcd. 352.0280.

[0042] The spectral property test of example 5 dye sensitizers

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Abstract

The invention relates to a coumarin functional dye containing a thiophene bridge chain in the field of fine chemical industry and organic photoelectric material applications. The structure of the coumarin functional dye takes coumarin and a derivative thereof as an electron donor, contains a thiophene structure unit capable of adjusting an absorption spectrum and a fluorescence emission spectrum as the bridge chain and is further connected with a cyanoacetic acid electron withdrawing group. Coumarin-thiophene, POCl3 / DMF (dimethyl fumarate) are added into a reaction container by adopting general reaction for reaction so as to get a 5-(7-substiutted-2-carbonyl-2H-benzopyran-3-yl) thiophene-2-formaldehyde intermediate (II) with an aldehyde group; and the intermediate II with the aldehyde group further reacts with cyanoacetic acid to get the coumarin dye connected by the thiophene. As the coumarin is taken as a chromophore, the electron donating capability is good; the thiophene has high electron cloud density and special optical properties and electron transmission capability; and the electron withdrawing group of the cyanoacetic acid is further connected for enabling the dye to have good light, thermal and chemical stability and photoelectric properties. Therefore, the dye can be used as a photosensitive dye for dye-sensitized solar cells.

Description

(1) Technical field [0001] The invention relates to the synthesis and application of a coumarin type dye sensitizer. (2) Background technology [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] At present, 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C09B57/02H01G9/20H01G9/042
CPCY02E10/542
Inventor 韩亮叶青李郁锦高建荣
Owner ZHEJIANG UNIV OF TECH
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