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Organic dye sensitizer and preparation method thereof

A technology of organic dyes and sensitizers, applied in the directions of organic dyes, chemical instruments and methods, photosensitive equipment, etc., can solve the problems of yield and energy conversion efficiency to be improved, high cost, cumbersome and other problems, and achieve good practical application value, The effect of low production cost and common and easy-to-obtain raw materials

Inactive Publication Date: 2014-08-13
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this patent requires more cumbersome steps to synthesize the product, and the cost is still high
Authorized Chinese patent application CN201010580802 discloses a class of organic dye sensitizers containing porphyrin macrocycles and a preparation method thereof, and its yield and energy conversion efficiency still need to be improved

Method used

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  • Organic dye sensitizer and preparation method thereof
  • Organic dye sensitizer and preparation method thereof
  • Organic dye sensitizer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] A kind of organic dye sensitizer whose chemical structural formula is 1, its synthetic route is as follows:

[0047]

[0048] (1) chemical structural formula is the synthesis of the intermediate of b:

[0049] Add compound a (0.50g, 1.6mmol), compound 1-hexenal (0.27g, 2.7mmol), and 25mL THF into a 100mL two-neck flask. Stir for half an hour under the protection of nitrogen, and then slowly dropwise add a THF solution in which 0.25 g (2.2 mmol) of potassium tert-butoxide is dissolved. Stir for 1 hour after dropping, and then slowly raise the temperature to 50°C. React for 12 hours. After cooling to room temperature, it was extracted with dichloromethane, followed by MgSO 4 Dry, filter and spin dry. Use petroleum ether as the eluent to pass through a silica gel column. A light yellow liquid was obtained with a yield of 68%. 1 H NMR (400MHz, CDCl 3 ,δ / ppm):7.20-7.19(d,1H,J=5.17Hz),7.09-7.08(d,1H,J=6.00Hz),6.65-6.58(m,1H),6.45-6.41(m,1H ),6.24-6.18(m,1H),5.87-5....

Embodiment 2

[0059] The synthetic route of the organic dye sensitizer whose chemical structural formula is 2 is as follows:

[0060]

[0061] (1) chemical structural formula is the synthesis of the intermediate of b:

[0062] Add compound a (0.50g, 1.6mmol), compound 1-hexenal (0.27g, 2.7mmol), and 25mL THF into a 100mL two-neck flask. Stir for half an hour under the protection of nitrogen, and then slowly dropwise add a THF solution in which 0.25 g (2.2 mmol) of potassium tert-butoxide is dissolved. Stir for 1 hour after dropping, and then slowly raise the temperature to 50°C. React for 12 hours. After cooling to room temperature, it was extracted with dichloromethane, followed by MgSO 4 Dry, filter and spin dry. Use petroleum ether as the eluent to pass through a silica gel column. A light yellow liquid was obtained with a yield of 68%. 1 H NMR (400MHz, CDCl 3 ,δ / ppm):7.20-7.19(d,1H,J=5.17Hz),7.09-7.08(d,1H,J=6.00Hz),6.65-6.58(m,1H),6.45-6.41(m,1H ),6.24-6.18(m,1H),5.87-5.80(m...

Embodiment 3

[0072] The synthetic route of the organic dye sensitizer whose chemical structural formula is 3 is as follows:

[0073]

[0074] (1) chemical structural formula is the synthesis of the intermediate of i:

[0075] Add compound a (0.50g, 1.6mmol), compound 5-hexylthiophene 2-carbaldehyde (0.53g, 2.7mmol), 25mL THF into a 100mL two-necked flask. Stir for half an hour under the protection of nitrogen, and then slowly dropwise add 30 mL of a THF solution in which 0.27 g (2.4 mmol) of potassium tert-butoxide is dissolved. Stir for 1 hour after dropping, and then slowly raise the temperature to 50°C. React for 24 hours. After cooling to room temperature, it was extracted with dichloromethane, followed by MgSO 4 Dry, filter and spin dry. Use petroleum ether as the eluent to pass through a silica gel column. A yellow liquid was obtained with a yield of 64%. 1 H NMR (400MHz, CDCl 3 ,δ / ppm):7.26(s,1H),7.18-7.16(d,1H,J=5.32Hz),7.07-7.05(d,1H,J=7.98Hz),6.90(s,1H),6.81- 6.79(d,1H...

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Abstract

The invention discloses an organic dye sensitizer with semi-rigid conjugated side groups and a preparation method of the organic dye sensitizer. The organic dye sensitizer has a D-pi-A structure and has the advantages of stable structure, easily available common raw materials and low production cost. The organic dye sensitizer is applied in preparing dye-sensitized solar cells to obtain a better effect that the energy conversion efficiency is 7-8% under the condition that the device is optimized and the organic dye sensitizer has certain practical application value.

Description

technical field [0001] The invention relates to an organic dye sensitizer for dye-sensitized solar cells and a preparation method thereof. Background technique [0002] Since the advent of dye-sensitized nano-titanium dioxide thin-film solar cells (DSSCs) in 1991 (Nature, 1991, 353, 737), this type of battery has been used for its relatively cheap raw materials, simple preparation process, and high photoelectric conversion efficiency. aroused great research interest. So far, the highest energy conversion efficiency of DSSCs battery has reached 13% (Nat. Chem., 2014, 6, 1861). In DSSCs, ruthenium-containing dyes are the most efficient in the early research period, with an energy conversion efficiency exceeding 10% (J. Am. Chem. Soc., 2001, 123, 1613-1624). However, ruthenium dyes have disadvantages such as limited resources and high price, which limit its application. Compared with the limited resources of ruthenium dyes, organic dyes have the advantages of easy design and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10H01G9/20
CPCY02E10/542
Inventor 谭松庭刘勋山陈华杰龙军卢昆
Owner XIANGTAN UNIV
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