Synthetic Pathways of <i>trans</i>-Substituted Porphyrins Bearing Pentafluorophenyl Groups from Dipyrromethanes
Different approaches were evaluated to obtain 5,15-bis [4-(<i>N</i>,<i>N</i>-diphenyl)aminophenyl]-10,20-bis(pentafluorophenyl)porphyrin and 5,15-bis [4-(9-carbazolyl)phenyl]-10,20-bis(pentafluorophenyl)porphyrin. First, the reaction of 5-pentafluorophenyldypyrromethane with...
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| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-11-01
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| Series: | Chemistry Proceedings |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2673-4583/16/1/114 |
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| Summary: | Different approaches were evaluated to obtain 5,15-bis [4-(<i>N</i>,<i>N</i>-diphenyl)aminophenyl]-10,20-bis(pentafluorophenyl)porphyrin and 5,15-bis [4-(9-carbazolyl)phenyl]-10,20-bis(pentafluorophenyl)porphyrin. First, the reaction of 5-pentafluorophenyldypyrromethane with the corresponding benzaldehyde catalyzed by boron trifluoride diethyl etherate in dichloromethane led to a high level of scrambling that produced a mixture of porphyrins. These products involve ABAB (3%), A<sub>3</sub>B (15%), and A<sub>4</sub> (4%) symmetries, where A represents a pentafluorophenyl group. These porphyrins have similar polarities and they are very difficult to separate by column chromatography. Therefore, the reagents were changed to pentafluorobenzaldehyde and dipyrromethane. When a 0.5:1 molar ratio was used, A<sub>4</sub> porphyrin was not obtained, and the main products were ABAB (19%) and A<sub>3</sub>B (6%). Therefore, condensation of a dipyrromethane with pentafluorobenzaldehyde provides a general method for the rational synthesis of ABAB-porphyrins in good yield with lower scrambling. |
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| ISSN: | 2673-4583 |