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Expanded Porphyrin Contraction: From [22]Triphyrin(6.6.0) to [22]Triphyrin(6.5.0)
Author(s) -
PacholskaDudziak Ewa,
HojniakThyssen Sandra,
LatosGrażyński Lechosław
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.201903181
Subject(s) - annulene , chemistry , porphyrin , moiety , protonation , pyrrole , carbon chain , stereochemistry , medicinal chemistry , ion , photochemistry , organic chemistry
An expanded triphyrin containing a bipyrrole moiety and annulene links, namely tetraphenyl‐[22]triphyrin(6.5.0), 2 , has been synthesized. The synthesis proceeded by a postsynthetic transformation of tetraphenyl‐[22]triphyrin(6.6.0), 1 , in a metal‐free unexpected and unprecedented ring contraction during column chromatography on alumina. The observed transformation, located at the hydrocarbon chain linking the pyrrole units, formally corresponds to a subtraction of one carbon atom from an annulene circuit. In contrast to the flexible substrate 1 , the product 2 is conformationally rigid, and capable of chloride anion binding in its protonated form.