Large conjugated half cyanine dye, its synthesis and its sensitized nano-crystal semiconductor solar energy battery

A technology of bonding and compounding, applied in semiconductor devices, semiconductor/solid-state device manufacturing, circuits, etc., can solve the problem of insufficient capture ability and achieve good photoelectric conversion function

Inactive Publication Date: 2006-04-26
PEKING UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0018] However, the pure organic dyes reported above are not strong enough to capture sunlight, and the maximum absorption peaks in the ultraviolet-visible spectrum are all lower than 550nm

Method used

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  • Large conjugated half cyanine dye, its synthesis and its sensitized nano-crystal semiconductor solar energy battery
  • Large conjugated half cyanine dye, its synthesis and its sensitized nano-crystal semiconductor solar energy battery
  • Large conjugated half cyanine dye, its synthesis and its sensitized nano-crystal semiconductor solar energy battery

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: N-(3-sulfonate propyl)-2-[2-(4-N,N-dimethylaminophenyl)vinyl]pyridine Onium Synthesis of Inner Salt (Dye-1)

[0083]

[0084] (1) Preparation of N-(3-sulfonate propyl)-2-picoline inner salt

[0085] 0.93g (0.01mol) of 2-picoline and 1.22g (0.01mol) of 1,3-propiolactone sulfonate were dissolved in 20mL of dry benzene and refluxed for 48h, then cooled at room temperature. The solid was collected by suction filtration and washed with anhydrous benzene to obtain 1.46 g of N-(3-sulfopropyl)-2-picoline inner salt as a white solid. Yield 68%.

[0086] (2) Synthesis of N-(3-sulfonate propyl group)-2-[2-(4-N, N-dimethylaminophenyl) vinyl] pyridinium inner salt

[0087] 0.215 g (0.001 mol) of the product of the above step was dissolved in 30 mL of absolute ethanol, and 0.149 g (0.001 mol) of 4-N, N-dimethylaminobenzaldehyde and a drop of hexahydropyridine were added. The reaction mixture was refluxed for 16h with stirring. Cool to room temperature. The reac...

Embodiment 2

[0091] Example 2: N-(3-sulfonate propyl)-2-[2-(4-N,N-diethylaminophenyl)vinyl]pyridine Synthesis of Inner Salt (Dye-2)

[0092]

[0093] Synthesize according to the method described in Example 1, just replace 4-N, N-dimethylaminobenzaldehyde with 4-N, N-diethylaminobenzaldehyde. After recrystallization from ethanol, 0.285 g of the target compound was obtained as orange-red crystals, with a yield of 76%. m.p.258~9℃.

[0094] Elemental Analysis C 20 h 26 N 2 o 3 S: Calculated: C, 64.14; H, 7.00; N, 7.48. Found: C, 63.96; H, 6.94; N, 7.16.

[0095] 1 H(500MHz, DMSO) δ: 1.14(t, 6H, J=6.90Hz) 2.16(m, 2H) 2.60(t, 2H, J=6.17Hz) 3.45(q, 4H, J=6.90Hz) 4.85(t , 2H, J = 6.93Hz) 6.74 (d, 2H, J = 8.71Hz) 7.45 (d, 1H, J = 15.56Hz) 7.69 (t, 1H, J = 6.61Hz) 7.83 (d, 2H, J = 8.71 Hz) 7.96 (d, 1H, J = 15.51 Hz) 8.30 (t, 1H, J = 7.88 Hz) 8.49 (d, 1H, J = 8.50 Hz) 8.74 (d, 1H, J = 6.27 Hz).

[0096] IR (cm -1 ): 2973, 1586, 1555, 1523, 1436, 1407, 1334, 1273, 1193, 1152, 1038, 81...

Embodiment 3

[0097] Example 3: 1-(3-sulfopropyl)-4-[2-(4-N,N-dimethylaminophenyl)vinyl]pyrimidine Synthesis of Salt (Dye-3)

[0098]

[0099] Synthesized according to the method described in Example 1, except that 2-methylpyridine was replaced by 2-methylpyrimidine. After purification by column chromatography (silica gel column, methanol:chloroform=1:8), 0.215 g of the target compound was obtained as a purple solid, with a yield of 62%. m.p.281~2℃.

[0100] Elemental Analysis C 17 h 21 N 3 o 3 S: Calculated: C, 58.77; H, 6.09; N, 12.09. Found: C, 58.71; H, 6.32; N, 11.96.

[0101] 1 H(500MHz, DMSO) δ: 2.19~2.24(m, 2H) 2.48(t, 2H, J=6.11Hz) 3.07(s, 6H) 4.48(t, 2H, J=6.95Hz) 6.82(d, 2H, J = 8.87Hz) 7.23 (d, 1H, J = 15.48Hz) 7.72 (d, 2H, J = 8.83Hz) 7.91 (d, 1H, J = 6.81Hz) 8.26 (d, 1H, J = 15.48Hz) 8.93 (dd, 1H, J = 6.84, 1.30 Hz) 9.37 (s, 1H).

[0102] IR (cm -1 ): 3048, 2917, 1577, 1530, 1451, 1375, 1337, 1293, 1162, 1041, 942, 826, 731, 524.

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Abstract

The present invention discloses novel solar cell sensitizers, more specifically, the present invention discloses a general formula D-π with electron donor-π conjugated system-electron acceptor (D-π-A) molecular structure -A-Q-G, the hemicyanine dye that contains sulfonic acid or carboxylic acid, compared with the known hemicyanine dye sensitizer, the degree of conjugation of this type of sensitizer is large, and the nanocrystalline semiconductor solar cell sensitized by it has High conversion rate, good stability and excellent effect.

Description

technical field [0001] The present invention relates to novel solar cell sensitizers, and more particularly, the present invention relates to sulfonic or carboxylic acid-containing hemicyanine dyes useful as solar cell sensitizers, compared to known hemicyanine dye sensitizers , this type of sensitizer has a large degree of conjugation, and the sensitized nanocrystalline semiconductor solar cell has excellent effects of high conversion rate and good stability. Background technique [0002] With the continuous growth of the world population, human beings are faced with two major problems of food and energy. The development of new clean energy has become an important issue. [0003] According to statistics, the annual solar radiation reaching the ground is 3×10 24 J (equivalent to 1.3 million tons of standard coal), if a solar cell with a conversion efficiency of 10% covers 1 / 1000 of the global surface, it can meet the energy needs of all mankind. Therefore, converting sola...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/80C07D215/12C07D263/32C07D277/26H01L31/0256H01L51/00H01L51/42
CPCY02E10/549H10K85/652H01G9/2059
Inventor 李富友黄春辉单璐姚巧红
Owner PEKING UNIV
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