Porphyrinoid rotaxanes: Building a mechanical picket fence
Porphyrinoid rotaxanes: Building a mechanical picket fence
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.
6679-6685
Ngo, Thien Huynh
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Labuta, Jan
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Lim, Gary N.
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Webre, W.
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D'Souza, Francis
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Karr, Paul A.
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Lewis, James E.M.
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Hill, Jonathan P.
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Ariga, Katsuhiko
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Goldup, Stephen
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1 September 2017
Ngo, Thien Huynh
a6697de9-4b83-4eeb-b516-e05b33cc437a
Labuta, Jan
54af3cc4-f269-4331-b98a-028e4711f493
Lim, Gary N.
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Webre, W.
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D'Souza, Francis
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Karr, Paul A.
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Lewis, James E.M.
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Hill, Jonathan P.
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Ariga, Katsuhiko
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Goldup, Stephen
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Ngo, Thien Huynh, Labuta, Jan, Lim, Gary N., Webre, W., D'Souza, Francis, Karr, Paul A., Lewis, James E.M., Hill, Jonathan P., Ariga, Katsuhiko and Goldup, Stephen
(2017)
Porphyrinoid rotaxanes: Building a mechanical picket fence.
Chemical Science, 8 (9), .
(doi:10.1039/C7SC03165C).
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.
Text
rvsd MS Ngo Porphyrin Chem Sci
- Accepted Manuscript
More information
Accepted/In Press date: 3 August 2017
e-pub ahead of print date: 4 August 2017
Published date: 1 September 2017
Identifiers
Local EPrints ID: 412998
URI: http://eprints.soton.ac.uk/id/eprint/412998
ISSN: 1478-6524
PURE UUID: 8826514d-67d0-42e2-907a-25b11e04a610
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Date deposited: 10 Aug 2017 16:30
Last modified: 15 Mar 2024 15:32
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Contributors
Author:
Thien Huynh Ngo
Author:
Jan Labuta
Author:
Gary N. Lim
Author:
W. Webre
Author:
Francis D'Souza
Author:
Paul A. Karr
Author:
James E.M. Lewis
Author:
Jonathan P. Hill
Author:
Katsuhiko Ariga
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