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One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso ‐CF 3 Groups
Author(s) -
Chen QiuCheng,
Soll Matan,
Mizrahi Amir,
Saltsman Irena,
Fridman Natalia,
Saphier Magal,
Gross Zeev
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710106
Subject(s) - trifluoromethyl , corrole , protonation , chemistry , tetra , crystal structure , tris , stereochemistry , medicinal chemistry , crystallography , photochemistry , organic chemistry , ion , biochemistry , alkyl
Corrole and sapphyrin with the smallest meso ‐substituents reported so far were prepared in a one‐pot synthesis that relies on a non‐aldehydic precursor for introducing CF 3 groups. The substantial amounts of products obtained by this facile pathway allowed for the full characterization of 5,10,15‐tris(trifluoromethyl)corrole, the access to a variety of stable chelates thereof and investigations that disclose the unique structural and chemical properties induced by the CF 3 substituents. The novel 5,10,15,20‐tetra(trifluoromethyl)sapphyrin undergoes only single protonation, which according to its crystal structure is stabilized by favorable non‐bonding F/H interaction between the meso ‐CF 3 and the inverted pyrrolic NH.