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Shaping a Porphyrinoid Frame by Heteroatoms Extrusion: Formation of an Expanded [22]Triphyrin(6.6.0)
Author(s) -
PacholskaDudziak Ewa,
LatosGrażyński Lechosław,
Białońska Agata
Publication year - 2019
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.201901571
Subject(s) - heteroatom , moiety , annulene , protonation , chemistry , tellurium , pyrrole , conformational isomerism , adamantane , crystallography , supramolecular chemistry , solvent , stereochemistry , ion , polymer chemistry , molecule , organic chemistry , crystal structure , ring (chemistry)
An aromatic expanded triphyrin, [22]triphyrin(6.6.0) 2 , containing a pyrrole unit, a bipyrrole moiety, and annulene links, was obtained from a tellurium‐containing precursor meso ‐tetraaryl‐26,28‐ditellurasapphyrin 1 . The reaction path proceeds through an acid‐promoted tellurium extrusion from 1 yielding directly 2 , characterized in a dicationic form by X‐ray crystallography. In solution the neutral macrocycle 2 reveals flexibility typical for annulenes and it exists as a mixture of conformers that differ by the configuration of the annulene fragments, as proven by 1 H NMR studies and analyzed by DFT methods. The conformation is controlled by protonation state, the nature of an interacting anion, solvent identity, and by interaction with water.