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Incorporation of a p ‐Phenylene Unit into the Azuliporphyrinogens Frame—Oxidation and Ruthenium Cluster Coordination
Author(s) -
Sprutta Natasza,
Hassa Agnieszka,
Białek Michał J.,
KodźWichowska Karolina,
Kupietz Kamil,
LatosGrażyński Lechosław
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802972
Subject(s) - dication , chemistry , ruthenium , phenylene , cluster (spacecraft) , thiophene , nucleophile , monomer , medicinal chemistry , stereochemistry , photochemistry , crystallography , polymer chemistry , molecule , organic chemistry , catalysis , computer science , programming language , polymer
A porphyrinogen macrocycle incorporating two azulenes, phenylene and thiophene into the framework, joined by four C(sp 3 ) atoms has been obtained as a mixture of six isomers. They were successfully separated and characterized spectroscopically. The identity of two of them was confirmed by X‐ray crystallography. One isomer was tested in reaction with [Ru 3 (CO) 12 ] yielding exclusively π‐complex with two clusters attached to azulenes. The partial oxidation of porphyrinogens yielded dication with two unmodified meso bridges. The stepwise oxidation followed by reaction with water as nucleophile afforded the dicationic species with two hydroxyl groups and a trication with one OH group. The hydroxy‐dication can be reversibly transformed into hydroxy‐trication by addition of HBF 4 etherate.