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Conjugate extension carboxyl dipyridyl ligand and synthetic method and application for ruthenium dye thereof

A technology of carboxybipyridine and bipyridine, which is applied in the field of synthesis of conjugated extended carboxybipyridine ligands and ruthenium-based dyes, can solve the problems of narrow absorption range and poor use of sunlight in the long-wave region, and achieve the goal of using Sufficient, improve the molar extinction coefficient, the effect of good application prospects

Active Publication Date: 2013-10-16
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that the absorption range is relatively narrow, and it cannot make good use of sunlight in the long-wave region

Method used

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  • Conjugate extension carboxyl dipyridyl ligand and synthetic method and application for ruthenium dye thereof
  • Conjugate extension carboxyl dipyridyl ligand and synthetic method and application for ruthenium dye thereof
  • Conjugate extension carboxyl dipyridyl ligand and synthetic method and application for ruthenium dye thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis method and conditions of ligand a: synthesize ligand a in ethanol with 2,2'-bipyridine-4,4'-dicarbaldehyde, malonic acid and tetrahydropyrrole;

[0033] Ligand a (4,4'-bis(2,2-dicarboxylic acid-1-vinyl)-2,2'-bipyridyl) synthetic route:

[0034]

[0035] The specific steps are: add 0.25g (2.4mmol) 2,2'-bipyridyl-4,4'-dicarbaldehyde, 0.75g (7.2mmol) malonic acid and 0.08g tetrahydropyrrole to the reaction tank filled with 30mL ethanol In the flask, stir for 0.5 hour to make it evenly mixed, then reflux at 95°C for 4 hours, let stand for 10 hours, vacuum filter, and wash with acetonitrile to obtain the final product.

[0036] Ligand a: 1H-NMR (298K, 200MHz, δin ppm) 7.7(m, 2H), 7.8~7.9(m, 2H), 8.1(s, 2H), 8.8(m, 2H), 9.1(s, 2H ),See figure 1 .

Embodiment 2

[0038] Ligand b synthesis method and conditions: 4,4'-dicarbaldehyde-2,2'-bipyridine, cyanoacetic acid and tetrahydropyrrole synthesize ligand b in acetonitrile;

[0039] Ligand b (4,4'-bis(2-cyano-1-acrylic acid)-2,2'-bipyridyl) synthetic route:

[0040]

[0041] The specific steps are: add 0.25g (2.4mmol) 2,2'-bipyridyl-4,4'-dicarbaldehyde, 0.61g (7.2mmol) cyanoacetic acid and 0.08g tetrahydropyrrole to the reaction tank filled with 30mL acetonitrile In the flask, stir for 0.5 hours to make it evenly mixed, then reflux at 105°C for 5 hours, let stand for 9 hours, vacuum filter, and wash with acetonitrile.

[0042] Ligand b: 1H-NMR (298K, 200MHz, δin ppm) 7.6~7.9(m, 4H), 8.3(m, 2H), 8.5~8.9(m, 2H), 12.7(s, 4H), see figure 2 .

Embodiment 3

[0044] Synthesis method of symmetrical ruthenium dye L121 based on ligand a: ligand a, RuCl 3 , NH 4 NCS synthesizes L121 in DMF;

[0045] L121 (ruthenium (bis(4,4'-bis(2,2-dicarboxylic acid-1-vinyl)-2,2'-bipyridine) (NCS) 2 )synthetic route:

[0046]

[0047] The specific steps are: add 0.058g (0.16mmol) ligand a, 0.017g (0.082mmol) RuCl 3 Added to 30mL DMF, stirred for 0.5 hours to mix, refluxed at 160°C for 4 hours, added 0.5g (6.57mmol) NH4 NCS, reflux at 130°C for 4 hours, and the entire reaction process was carried out in a nitrogen atmosphere. Let stand for 10 hours, vacuum filter, wash 3 times with water, and then 4 times with ether. Vacuum dry.

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Abstract

The invention discloses a conjugate extension carboxyl dipyridyl ligand, synthesizes two new symmetric ruthenium dyes, namely L121 and L122, and two dissymmetric ruthenium dyes, namely L123 and L124, based the conjugate extension carboxyl dipyridyl ligand through one-pot method. Compared with the experiment data of N3 dye, visible absorption peak of L121-L122 emerge remarkable red shift, and the intensity of the absorption peak is increased accordingly. Therefore, the novel dye is provided with better light absorption when comparing with classical N3 dye, and has better application prospect in dye-sensitized solar cell.

Description

technical field [0001] The invention relates to a synthesis method and application of a conjugated extended carboxybipyridine ligand and a ruthenium dye, and belongs to the technical field of synthetic chemistry. Background technique [0002] In recent years, the energy issue has become one of the most important issues facing mankind today. Whether new energy sources that can effectively replace fossil fuels can be found is the key to solving energy problems. Therefore, all countries in the world are striving to develop new energy while saving existing energy. Among them, solar energy is a research hotspot in recent years. Photoelectric conversion power generation through solar cells is considered to be the most effective way to utilize solar energy, and solar cells are pollution-free, which can not only alleviate the problem of energy shortage, but also meet the strategic goal of sustainable development in my country. [0003] Silicon-based solar cells are characterized ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C07D213/55C09B57/10H01G9/20
CPCY02E10/542
Inventor 孙花飞孙元伟张宪玺杜玉昌
Owner LIAOCHENG UNIV