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Issue 10, 2011
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Template-directed synthesis of π-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring

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Abstract

[2]Rotaxanes consisting of butadiyne-linked porphyrin dimers threaded through a phenanthroline-containing macrocycle, can be synthesised by an active-metal template directed copper-mediated Glaser coupling, in yields of up to 61%, without requiring a large excess of the macrocycle. The crystal structure of one of these rotaxanes confirms that the macrocycle is clasped around the centre of the porphyrin dimer. A radial hexa-pyridyl template was used to convert the alkyne-terminated [2]rotaxane into a [4]catenane cyclic porphyrin hexamer in 62% yield, viapalladium-catalysed Glaser coupling. The related [7]catenane porphyrin dodecamer complex was also isolated as a by-product of this cyclisation, in 6% yield. These results illustrate the scope of template-directed synthesis for creating complex interlocked structures directly from simple starting materials.

Graphical abstract: Template-directed synthesis of π-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring

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Article information


Submitted
12 Jun 2011
Accepted
02 Jul 2011
First published
28 Jul 2011

Chem. Sci., 2011,2, 1897-1901
Article type
Edge Article

Template-directed synthesis of π-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring

M. J. Langton, J. D. Matichak, A. L. Thompson and H. L. Anderson, Chem. Sci., 2011, 2, 1897
DOI: 10.1039/C1SC00358E

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