Results
Title

Expanded Porphyrin Contraction: From [22]Triphyrin(6.6.0) to [22]Triphyrin(6.5.0).

Authors

Pacholska‐Dudziak, Ewa; Hojniak‐Thyssen, Sandra; Latos‐Grażyński, Lechosław

Abstract

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.

Subjects

PORPHYRINS; COLUMN chromatography; ALUMINUM oxide

Publication

Chemistry - A European Journal, 2019, Vol 25, Issue 51, p11859

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.201903181