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Nucleophilic Substitution Reactions of meso ‐5,10,15‐Tris(pentafluorophenyl)corrole; Synthesis of ABC‐Type Corroles and Corrole‐Based Organogels
Author(s) -
Hori Takaaki,
Osuka Atsuhiro
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901500
Subject(s) - corrole , chemistry , nucleophile , nucleophilic substitution , photochemistry , substituent , tris , substitution reaction , amine gas treating , medicinal chemistry , organic chemistry , catalysis , biochemistry
Nucleophilic substitution reactions of 5,10,15‐tris(pentafluorophenyl)corrole ( 1 ) with amines were examined as a post‐modification route to functional corroles. Reaction of 1 with an excess of amine nucleophiles led to exclusive formation of 5,10,15‐tris(4‐amino‐2,3,5,6‐tetrafluorophenyl)‐substituted corroles. In this nucleophilic reaction, 5‐ and 15‐pentafluorophenyl substituents were found to be more reactive than the substituent at the 10‐position. This substitution reaction was applied for the preparation of ABC‐type corroles and corrole‐based organogels. The latter exhibited a blue‐shifted Soret band and small fluorescence quantum yields in nonpolar hydrocarbon solvents due to the formation of H‐type aggregates.