Porphyrinoid rotaxanes: building a mechanical picket fence

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This article describes the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield.

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7 p.

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Ngo, T. H.; Labuta, J.; Lim, G. N.; Webre, W. A.; D'Souza, Francis; Karr, P. A. et al. August 3, 2017.

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This article describes the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield.

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7 p.

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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.

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  • Chemical Science, 2017. London, UK: Royal Society of Chemistry

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  • Publication Title: Chemical Science
  • Volume: 8
  • Pages: 6679-6685
  • Peer Reviewed: Yes

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UNT Scholarly Works

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  • July 19, 2017

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  • August 3, 2017

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  • August 3, 2017

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  • Aug. 29, 2017, 9:38 a.m.

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Ngo, T. H.; Labuta, J.; Lim, G. N.; Webre, W. A.; D'Souza, Francis; Karr, P. A. et al. Porphyrinoid rotaxanes: building a mechanical picket fence, article, August 3, 2017; London, United Kingdom. (digital.library.unt.edu/ark:/67531/metadc990938/: accessed October 22, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.