Synthesis of middle position-tetraaryldiphenanthrene dioxyporphyrin derivative and application thereof

A technology of tetraaryl diphenanthrene and dioxoporphyrin, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of many by-products, low yield, difficult purification, etc., and improve the absorption efficiency , Molar absorptivity increases, and the effect of improving conversion efficiency

Inactive Publication Date: 2008-07-02
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-tetraaryldiphenanthrene dioxyporphyrin derivative and application thereof
  • Synthesis of middle position-tetraaryldiphenanthrene dioxyporphyrin derivative and application thereof
  • Synthesis of middle position-tetraaryldiphenanthrene dioxyporphyrin derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: 5,10,15,20-tetraphenyl-diphenanthrene[9,10-b:9,10-l]-22,24-dioxoporphyrin (1a) was synthesized in a 250ml circle Add 1mmol (278mg) 2,5-bis(phenylhydroxymethyl)furan, 1mmol (217mg) phenanthropyrrole and 60ml 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 -40-±5°C, add a total of 80 μl 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. 1.0 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 dark green crystals were obtained after recrystallization from methanol and chloroform. Yield: 31.9%; melting point: >250°C; MALDI-TOF MASS cacd for C 68 h 40 N 2 o 2 917....

Embodiment 2

[0032] Example 2: 5,10,15,20-tetrakis(4-fluorophenyl)-diphenanthrene[9,10-b:9,10-l]-22,24-dioxoporphyrin (1b) The synthetic preparation method is the same as in Example 1, and the yield: 15.9%. Melting point: >250℃; MALDI-TOF MASS cacd for C 68 h 36 f 4 N 2 o 2 989.02, found: (M+H + )(Figure 5); 1 H-NMR (d 6 -DMSO) δ7.10-7.13 (4H, m), 7.43 (4H, s), 7.65 (8H, m), 7.83-7.85 (4H, m), 8.27 (4H, s); 8.63-8.64 (8H, m), 8.75 (4H, s); UV-vis (CHCl 3 )λmax,nm(ε×10 -5 )577 (0.715), 732 (0.0442), 808 (0.151) (Figure 6).

Embodiment 3

[0033] Example 3: 5,10,15,20-tetrakis(4-chlorophenyl)-diphenanthrene[9,10-b:9,10-l]-22,24-dioxoporphyrin (1c) The synthetic preparation method is the same as in Example 1, and the yield: 10.5%. Melting point: >250℃; MALDI-TOF MASS cacd for C 68 h 36 Cl 4 N 2 o 2 1054.84, found: (M+H + ) (Figure 7); 1 H-NMR (d 6 -DMSO) δ7.15-7.18 (8H, m), 7.48-7.51 (4H, m), 7.87-7.89 (8H, m), 8.32 (4H, s), 8.70-8.72 (8H, m), 8.82 ( 4H, s); UV-vis (CHCl 3 )λmax,nm(ε×10 -5 )577 (0.715), 732 (0.0442), 808 (0.151) (Figure 8).

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Abstract

The invention discloses a method for preparing 5,10,15,20-tetra-aryl diphenanthrene (9,10-b;9,10-1)-22,24-diseleno porphyrin compound by the reaction of phenanthro-pyrrole and 2,5-di(aryl hydroxyl methyl) selenophen at low temperature with the function of BF3 Et2O under water free and oxygen free condition. The Soret spectral bands of the compound appear in 521nm, compared with tetraphenyl diseleno porphyrin without conjugated aromatic ring at beta-site, the Soret spectral bands are red shifted by 52nm and enter green light zone above 500nm. The compound has wide application prospects in such areas as photodynamics therapy photosensitizer, OFETs (organic field effect tube), molecular antenna, light energy converter, optical conversion material, molecular switch, molecular logic gate, molecular wire, organic solar battery, organic electroluminescence, non-linear optical material, optical storage, molecular identification and medicine and so on.

Description

1. Technical field [0001] The present invention relates to 5,10,15,20-tetraaryldiphenanthrene[9,10-b:9,10-l]-22,24-dioxoporphyrin 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 photo-induced charge separation [see: (a) Gust D.Moore T.A.Scien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22C09K11/06
Inventor 沈珍徐海军游效曾
Owner NANJING UNIV
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