Issue 8, 2011

A noncovalently assembled porphyrinic catenane consisting of two interlocking [43]-membered rings

Abstract

A new macrocycle and the corresponding [2]catenane were prepared quantitatively from relatively large organic fragments using coordination chemistry bonds only (Zn–N bonds for the ring and Cu–N bonds for the catenane). The two constitutive macrorings of the [2]catenane are 43-membered rings. The organic components consist of a bis-Zn porphyrin and a 1,10-phenanthroline derivative, both fragments being significantly larger than those previously used for making related compounds. The catenane was assembled in two steps from a bis-Zn porphyrin and a 2,9-di(4′′-pyridyl-4′-phenyl)-1,10-phenanthroline. In a first step the entwined copper(I) complex of the phenanthroline derivative was formed via Cu(I)–N interactions. Subsequently, a double ring closing reaction was performed by coordination of two equivalents of bis-Zn porphyrin to the entwined copper(I) complex. The tetraporphyrinic [2]catenane was thus obtained thanks to the formation of four Zn(II)–pyridine bonds. It has a high association constant, 4 × 1010M−2, due to the good geometrical fit between the constituents.

Graphical abstract: A noncovalently assembled porphyrinic catenane consisting of two interlocking [43]-membered rings

Supplementary files

Article information

Article type
Paper
Submitted
04 Apr 2011
Accepted
02 May 2011
First published
08 Jun 2011

New J. Chem., 2011,35, 1751-1757

A noncovalently assembled porphyrinic catenane consisting of two interlocking [43]-membered rings

M. Beyler, V. Heitz and J. Sauvage, New J. Chem., 2011, 35, 1751 DOI: 10.1039/C1NJ20294D

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