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Meso position-tetra phenyl tetra phenanthro porphyrin derivetive and its preparation method

A technology for tetraphenyltetraphenanthrene and porphyrin compounds, which is applied in the field of meso-tetraphenyltetraphenanthroline porphyrin derivatives and their preparation, and can solve the problems of difficulty in synthesis, inability to coplanar, and impossible synthesis.

Inactive Publication Date: 2007-02-14
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1995, Lash successfully synthesized tetraphenanthrene porphyrin with no substituent in the middle position [see: Lash T.D., Novak B.H.Angew.Chem.Int.Ed.Engl.1995, 34, 683.], while there are substituents in the middle position The molecular weight of tetraphenyltetraphenanthrene porphyrin was only detected by FAB-MS. Some researchers believe that this kind of compound cannot be coplanar due to large steric hindrance, so it is difficult to synthesize or even Impossible to synthesize [Ref: Spence J.D., Lash T.D.J.Org.Chem.2000, 65, 1530.]

Method used

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  • Meso position-tetra phenyl tetra phenanthro porphyrin derivetive and its preparation method
  • Meso position-tetra phenyl tetra phenanthro porphyrin derivetive and its preparation method
  • Meso position-tetra phenyl tetra phenanthro porphyrin derivetive and its preparation method

Examples

Experimental program
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Embodiment 1

[0046] Embodiment 1: the synthesis of 5,10,15,20-tetraphenyltetraphenanthrene porphyrin (1a)

[0047] Add 1mmol (217mg) phenanthrenopyrrole and 350ml anhydrous dichloromethane into a 500ml round bottom flask, put in a magnet and start stirring, put the reaction bottle into a cryogenic device under the protection of argon and avoid light, use liquid nitrogen and acetone Control the reaction temperature at -40±10°C, add 1 mmol benzaldehyde with a syringe, and then add a total of 40 μl of BF dropwise with a micro-syringe 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 after 1 hour of reaction, triethylamine was added dropwise to neutralize the reactant. The solvent was distilled off under reduced pressure to obtain a black powder, which was packed into a 100-140 mesh silica gel column and chloroform-petroleum ethe...

Embodiment 2

[0048] Embodiment 2: the synthesis of 5,10,15,20-tetraphenyltetraphenanthrene porphyrin (1a)

[0049] The preparation method is the same as in Example 1, except that 1.2 mmol of benzaldehyde is added. Yield: 24%.

Embodiment 3

[0050] Embodiment 3: the synthesis of 5,10,15,20-tetraphenyltetraphenanthrene porphyrin (1a)

[0051] The preparation method is the same as in Example 1, except that 2 mmol benzaldehyde is added. Yield: 22%.

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Abstract

The present invention discloses tetraphenanthryl porphyrin derivative with different substituents in the mid position benzene ring and prepared through the BF3.Et2O catalyzed reaction of phenanthryl pyrrole and benzaldedyde with with different substituents in the para position at low temperature and in no-oxygen atmosphere. These conjugated porphyrin compounds have Soret band in 577-603 nm, red shifted by over 160 nm compared with that of no-aromatic ring conjugated beta-tetraphenyl porphyrin and red shifted by near 100 nm compared with that of phenanthrene ring conjugated porphyrin without substituent in the mid position. These conjugated porphyrin compounds have wide application foreground in OFETs, molecular antenna, light-to-energy converter, medicine and other fields.

Description

1. Technical field [0001] The invention relates to a meso-tetraphenyltetraphenanthrene porphyrin derivative 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, 1989, 244, 35. (b). Wasiele...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07D207/00C07D257/00
Inventor 沈珍徐海军游效曾
Owner NANJING UNIV
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