Porphyrinoid rotaxanes: building a mechanical picket fence† †Electronic supplementary information (ESI) available: Full synthetic procedures and characterisation of all novel compounds. See DOI: 10.1039/c7sc03165c
| Autor: | Ngo, T. H., Labuta, J., Lim, G. N., Webre, W. A., D'Souza, F., Karr, P. A., Lewis, J. E. M., Hill, J. P., Ariga, K., Goldup, S. M. |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: | |
| Zdroj: | Chemical Science |
| ISSN: | 2041-6539 2041-6520 |
| Popis: | We demonstrate that the threaded macrocycles in interlocked porphyrin–corrole conjugates provide a mechanical “picket fence” without affecting their electronic properties. 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. |
| Databáze: | OpenAIRE |
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