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Synthesis of middle position-tetraphenyldiphenanthrene disulphoporphyrin derivative and application thereof

A technology of tetraphenyldiphenanthrenedithioporphyrin and phenanthrenepyrrole, which is applied in the synthesis and application fields of meso-tetraphenyldiphenanthrenedithioporphyrin derivatives, and can solve the problem of many by-products. , difficult purification, low yield and other problems, to achieve the effect of improving conversion efficiency and absorption efficiency

Inactive Publication Date: 2007-08-15
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because pyrrole is prone to ring-opening polymerization and oxidation reactions under the action of catalysts, resulting in many by-products, difficult purification, and low yields, generally 10%, or even lower

Method used

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  • Synthesis of middle position-tetraphenyldiphenanthrene disulphoporphyrin derivative and application thereof
  • Synthesis of middle position-tetraphenyldiphenanthrene disulphoporphyrin derivative and application thereof
  • Synthesis of middle position-tetraphenyldiphenanthrene disulphoporphyrin derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Embodiment 1: 5,10,15,20-tetraphenyl-diphenanthrene[9,10-b:9,10-l]-22,24-dithioporphyrin (1a) synthesis in 250ml circle Add 1mmol (278mg) 2,5-bis(phenylhydroxymethyl)thiophene, 1mmol (217mg) phenanthropyrrole and 60ml of anhydrous dichloromethane into the bottom flask, put a magnet and start stirring, and react under the protection of argon. Put the bottle in a cryogenic device and keep it away from light, control the reaction temperature at -30±10°C, add a total of 0.17ml of BF 3 ·Et 2 O, after making it react at low temperature for 2 hours, allow it to naturally warm up to room temperature and continue the reaction for 48 hours. 1 mmol DDQ (227 mg) was added to the reaction solution, and reacted for 1 hour. The solvent was distilled off under reduced pressure for chromatographic separation, and purple-black crystals were obtained after recrystallization from methanol and chloroform. Yield: 15%; Melting point: >250°C; ESI MASS: calcd for C 68 h 40 N 2 S 2 949.2...

Embodiment 2

[0022] Embodiment 2: The synthetic preparation method of 5,10,15,20-tetraphenyl-diphenanthrene[9,10-b:9,10-l]-22,24-dithioporphyrin (1a) is the same as In Example 1, only 1.25 mmol of 2,5-bis(phenylhydroxyl)methylthiophene was added. Yield: 10%.

Embodiment 3

[0023] Embodiment 3: the synthesis of 5,10,15,20-tetraphenyltetraphenanthrene porphyrin (1a)

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Abstract

The invention discloses a making method of 5, 10, 15, 20-tetrabenadiphenanthroime [9, 10-b: 9, 10-l]-22, 24-dithioporphyrin compound, which is characterized by the following: reacting phenanthroime pyrrole and 2, 5-di (phenyl hydroxy methyl) thiofuran or 2, 5-di(4-chlorphenyl hydroxy methyl) thiofuran catalyzed by BF3.Et2O under low temperature; displaying 505nm in the Soret band; making the beta-non-aromatic conjugated tetraphenyl-dithioporphyrin move 70nm than red spectrum of Soret and 51nm than middle position-tetraphenyl-2, 3, 12, 13-tetraphenyl-21, 23-dithioporphyrin of lamda max S2TPP; entering into green area over 500nm; fitting for photosensitizer, OFETs, molecular antenna, light-energy switcher, photoelectric switching material, molecular switch, molecular logic door, molecular wire, organic solar energy battery, organic electroluminescent material and non-linear optical material.

Description

1. Technical field [0001] The invention relates to 5,10,15,20-tetraphenyldiphenanthrene[9,10-b:9,10-l]-22,24-dithioporphyrin derivatives and a preparation method thereof. 2. Background technology [0002] Porphyrin compounds have many unique photoelectric properties, good light and thermal stability, and have a large molar absorptivity in the visible light range, so they have been widely used in biochemistry, medicine, analytical chemistry, photocatalysis, and material science. It has received extensive attention and application. In recent years, using the unique electronic structure and photoelectric properties of porphyrin molecules, the design and synthesis of photoelectric functional materials and the development of photoelectric devices have become very active research fields at home and abroad. In terms of energy transfer, porphyrin molecules, as light-absorbing units in model compounds, can realize light-induced charge separation [see: (a) Gust D., Moore T.A. Science...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/22C07D209/56C07D333/06
Inventor 沈珍吴迪薛兆历沈康游效曾
Owner NANJING UNIV
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