Journal
CHEMICAL SCIENCE
Volume 8, Issue 9, Pages 6679-6685Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc03165c
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Funding
- International Center for Young Scientists (ICYS)
- World Premier International Research Center Initiative (WPI Initiative), MEXT
- JST CREST, Japan
- University of Southampton
- EPSRC [EP/L016621/1]
- Royal Society
- European Union's Horizon research and innovation programme under Marie Sklodowska-Curie grant [660731]
- European Research Council [724987]
- US-National Science Foundation [1401188]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1401188] Funding Source: National Science Foundation
- Engineering and Physical Sciences Research Council [EP/J01981X/1, EP/L016621/2] Funding Source: researchfish
- EPSRC [EP/L016621/2, EP/J01981X/1] Funding Source: UKRI
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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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