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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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Publication details

The article was received on 19 Jul 2017, accepted on 03 Aug 2017 and first published on 04 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03165C
Citation: Chem. Sci., 2017,8, 6679-6685
  • Open access: Creative Commons BY license
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    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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