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Thiatriphyrin(2.1.1): A Core‐Modified Contracted Porphyrin
Author(s) -
Kuzuhara Daiki,
Sakakibara Yuka,
Mori Shigeki,
Okujima Tetsuo,
Uno Hidemitsu,
Yamada Hiroko
Publication year - 2013
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.201209678
Subject(s) - porphyrin , core (optical fiber) , chemistry , materials science , photochemistry , composite material
Elusive in its free‐base form , the core‐modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p ‐tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy‐substituted analogues (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). In the presence of trifluoroacetic acid (TFA), each of these compounds was transformed into the protonated thiatriphyrin(2.1.1), which exhibited moderate aromaticity.