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
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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 tetraphenyltetraphe

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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Example Embodiment

[0046] Example 1: Synthesis of 5,10,15,20-tetraphenyltetraphenanthroporphyrin (1a)

[0047] Add 1mmol (217mg) phenanthropyrrole and 350ml of anhydrous dichloromethane to a 500ml round bottom flask, put it in a magnet, and start stirring. Under the protection of argon, put the reaction flask in a cryogenic device and protect from light. Use liquid nitrogen and acetone. Control the reaction temperature at -40±10℃, use a syringe to add 1 mmol benzaldehyde, and then use a micro syringe to add a total of 40μl of BF. 3 ·Et 2 O, let it react at low temperature for 2 hours, and then let it naturally rise to room temperature to continue the reaction for 48 hours. 1 mmol DDQ (227 mg) was added to the reaction solution, and after reacting for 1 hour, triethylamine was added dropwise to neutralize the reactant. The solvent was evaporated under reduced pressure to obtain black powder. The column was packed with 100-140 mesh silica gel and chloroform-petroleum ether was used as the eluent for c...

Example Embodiment

[0048] Example 2: Synthesis of 5,10,15,20-tetraphenyltetraphenanthroporphyrin (1a)

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

Example Embodiment

[0050] Example 3: Synthesis of 5,10,15,20-tetraphenyltetraphenanthroporphyrin (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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