A Zinc Porphyrin Bearing Two Lateral dpp-Containing Rings and Its [3]Pseudorotaxane (dpp: 2,9-diphenyl-1,10-phenanthroline)

A zinc porphyrin attached to two dpp‐containing rings was prepared from a 31‐membered ring with an attached pendent aldehyde function and 5‐mesityldipyrromethane by using the synthetic method introduced long ago by Lindsey and his group. The obtained porphyrin is of the ABAB type, with two mesityl g...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-06, Vol.2009 (17), p.2795-2800
Main Authors: Roche, Cécile, Sour, Angélique, Niess, Frédéric, Heitz, Valérie, Sauvage, Jean-Pierre
Format: Article
Language:English
Subjects:
Chemistry
Copper
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Macrocycles
Organic chemistry
Porphyrins
Preparations and properties
Rotaxanes
Template synthesis
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Summary:A zinc porphyrin attached to two dpp‐containing rings was prepared from a 31‐membered ring with an attached pendent aldehyde function and 5‐mesityldipyrromethane by using the synthetic method introduced long ago by Lindsey and his group. The obtained porphyrin is of the ABAB type, with two mesityl groups on the 5‐ and 15‐positions and two macrocycles on the 10‐ and 20‐positions. From this compound, a [3]pseudorotaxane was obtained in good yield from the reaction of the porphyrin with two equivalents of a copper(I) salt followed by the addition of two equivalents of 2,9‐dianisyl‐1,10‐phenanthroline.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The synthesis of a zinc‐complexed porphyrin bearing two coordinating macrocycles trans to each other is described. The ring‐containing ligands are 2,9‐diphenyl‐1,10‐phenanthroline derivatives. The copper(I)‐driven threading reaction of two 2,9‐dianisyl‐1,10‐phenanthroline chelates through the rings affords a [3]pseudorotaxane quantitatively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900136