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Issue 9, 2017
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Porphyrinoid rotaxanes: building a mechanical picket fence

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Abstract

Building on recent progress in the synthesis of functional porphyrins for a range of applications using the Cu-mediated azide–alkyne cycloaddition (CuAAC) reaction, we describe the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield. By synthesising interlocked analogues of previously studied porphyrin–corrole conjugates, we demonstrate that this approach gives access to rotaxanes in which the detailed electronic properties of the axle component are unchanged but whose steric properties are transformed by the mechanical “picket fence” provided by the threaded rings. Our results suggest that interlocked functionalised porphyrins, readily available using the AT-CuAAC approach, are sterically hindered scaffolds for the development of new catalysts and materials.

Graphical abstract: Porphyrinoid rotaxanes: building a mechanical picket fence

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Supplementary files

Article information


Submitted
19 Jul 2017
Accepted
03 Aug 2017
First published
04 Aug 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 6679-6685
Article type
Edge Article

Porphyrinoid rotaxanes: building a mechanical picket fence

T. H. Ngo, J. Labuta, G. N. Lim, W. A. Webre, F. D'Souza, P. A. Karr, J. E. M. Lewis, J. P. Hill, K. Ariga and S. M. Goldup, Chem. Sci., 2017, 8, 6679
DOI: 10.1039/C7SC03165C

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