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; S. M. Goldup

doi:10.1039/c7sc03165c

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, S. M. Goldup

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6679-6685
Number of pages	7
Journal	Chemical Science
Volume	8
Issue number	9
DOIs	https://doi.org/10.1039/c7sc03165c
Publication status	Published - 2017

Bibliographical note

Funding Information:
THN and JL thank the International Center for Young Scientists (ICYS) for support. This work was partly supported by the World Premier International Research Center Initiative (WPI Initiative), MEXT and JST CREST, Japan. THN thanks the Alexander von Humboldt Foundation and Institut für Chemie und Biochemie, Freie Universität Berlin for the continued support. SMG thanks the University of Southampton, EPSRC (EP/L016621/1) and Royal Society for nancial support. JEML is an EU Marie Skłodowska-Curie Fellow, receiving nancial support from the European Union's Horizon 2020 research and innovation programme under Marie Sklodowska-Curie grant agreement No 660731. SMG is a Royal Society Research Fellow. SMG acknowledges funding from the European Research Council (Consolidator Grant Agreement no. 724987). The authors are also grateful to the US-National Science Foundation (Grant No. 1401188 to FD) for support of this work.

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

ASJC Scopus subject areas

General Chemistry

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Cite this

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title = "Porphyrinoid rotaxanes: Building a mechanical picket fence",

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.",

author = "Ngo, {T. H.} and J. Labuta and Lim, {G. N.} and Webre, {W. A.} and F. D'Souza and Karr, {P. A.} and Lewis, {J. E.M.} and Hill, {J. P.} and K. Ariga and Goldup, {S. M.}",

note = "Funding Information: THN and JL thank the International Center for Young Scientists (ICYS) for support. This work was partly supported by the World Premier International Research Center Initiative (WPI Initiative), MEXT and JST CREST, Japan. THN thanks the Alexander von Humboldt Foundation and Institut f{\"u}r Chemie und Biochemie, Freie Universit{\"a}t Berlin for the continued support. SMG thanks the University of Southampton, EPSRC (EP/L016621/1) and Royal Society for nancial support. JEML is an EU Marie Sk{\l}odowska-Curie Fellow, receiving nancial support from the European Union's Horizon 2020 research and innovation programme under Marie Sklodowska-Curie grant agreement No 660731. SMG is a Royal Society Research Fellow. SMG acknowledges funding from the European Research Council (Consolidator Grant Agreement no. 724987). The authors are also grateful to the US-National Science Foundation (Grant No. 1401188 to FD) for support of this work. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7sc03165c",

language = "English",

volume = "8",

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T2 - Building a mechanical picket fence

AU - Ngo, T. H.

AU - Labuta, J.

AU - Lim, G. N.

AU - Webre, W. A.

AU - D'Souza, F.

AU - Karr, P. A.

AU - Lewis, J. E.M.

AU - Hill, J. P.

AU - Ariga, K.

AU - Goldup, S. M.

N1 - Funding Information: THN and JL thank the International Center for Young Scientists (ICYS) for support. This work was partly supported by the World Premier International Research Center Initiative (WPI Initiative), MEXT and JST CREST, Japan. THN thanks the Alexander von Humboldt Foundation and Institut für Chemie und Biochemie, Freie Universität Berlin for the continued support. SMG thanks the University of Southampton, EPSRC (EP/L016621/1) and Royal Society for nancial support. JEML is an EU Marie Skłodowska-Curie Fellow, receiving nancial support from the European Union's Horizon 2020 research and innovation programme under Marie Sklodowska-Curie grant agreement No 660731. SMG is a Royal Society Research Fellow. SMG acknowledges funding from the European Research Council (Consolidator Grant Agreement no. 724987). The authors are also grateful to the US-National Science Foundation (Grant No. 1401188 to FD) for support of this work. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

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DO - 10.1039/c7sc03165c

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JO - Chemical Science

JF - Chemical Science

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ER -

Porphyrinoid rotaxanes: Building a mechanical picket fence

Abstract

Bibliographical note

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