Self-induced porphyrin dimer formation via unusual atropisomerization of tetraphenylporphyrin derivative

Atropisomerization of meso-tetrakis( 2-carboxy-4-nonylphenyl)porphyrin 1, in nonpolar solvents such as CHCl 3 gives the αααα isomer exclusively, while the same isomerization in polar solvents such as DMSO proceeds normally. Spectroscopic investigations of 1 suggest that the porphyrin exists as a cof...

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Bibliographic Details
Published in:Tetrahedron letters 1995-11, Vol.36 (46), p.8449-8452
Main Authors: Kuroda, Yasuhisa, Kawashima, Ayato, Urai, Tadashi, Ogoshi, Hisanobu
Format: Article
Language:English
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Summary:Atropisomerization of meso-tetrakis( 2-carboxy-4-nonylphenyl)porphyrin 1, in nonpolar solvents such as CHCl 3 gives the αααα isomer exclusively, while the same isomerization in polar solvents such as DMSO proceeds normally. Spectroscopic investigations of 1 suggest that the porphyrin exists as a cofacial dimer in nonpolar solvents, where eight hydrogen bonds among tour pairs of carboxylic acids in 1 are formed.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)01819-4