Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring
[2]Rotaxanes consisting of butadiyne-linked porphyrin dimers threaded through a phenanthroline-containing macrocycle, can be synthesised by an active-metal template directed copper-mediated Glaser coupling, in yields of up to 61%, without requiring a large excess of the macrocycle. The crystal struc...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2011
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| _version_ | 1797058838306750464 |
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| author | Langton, M Matichak, J Thompson, A Anderson, H |
| author_facet | Langton, M Matichak, J Thompson, A Anderson, H |
| author_sort | Langton, M |
| collection | OXFORD |
| description | [2]Rotaxanes consisting of butadiyne-linked porphyrin dimers threaded through a phenanthroline-containing macrocycle, can be synthesised by an active-metal template directed copper-mediated Glaser coupling, in yields of up to 61%, without requiring a large excess of the macrocycle. The crystal structure of one of these rotaxanes confirms that the macrocycle is clasped around the centre of the porphyrin dimer. A radial hexa-pyridyl template was used to convert the alkyne-terminated [2]rotaxane into a [4]catenane cyclic porphyrin hexamer in 62% yield, via palladium-catalysed Glaser coupling. The related [7]catenane porphyrin dodecamer complex was also isolated as a by-product of this cyclisation, in 6% yield. These results illustrate the scope of template-directed synthesis for creating complex interlocked structures directly from simple starting materials. © The Royal Society of Chemistry 2011. |
| first_indexed | 2024-03-06T19:56:01Z |
| format | Journal article |
| id | oxford-uuid:259e2e12-c7e6-4195-9037-db9b6428304f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:56:01Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:259e2e12-c7e6-4195-9037-db9b6428304f2022-03-26T11:56:33ZTemplate-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoringJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:259e2e12-c7e6-4195-9037-db9b6428304fEnglishSymplectic Elements at Oxford2011Langton, MMatichak, JThompson, AAnderson, H[2]Rotaxanes consisting of butadiyne-linked porphyrin dimers threaded through a phenanthroline-containing macrocycle, can be synthesised by an active-metal template directed copper-mediated Glaser coupling, in yields of up to 61%, without requiring a large excess of the macrocycle. The crystal structure of one of these rotaxanes confirms that the macrocycle is clasped around the centre of the porphyrin dimer. A radial hexa-pyridyl template was used to convert the alkyne-terminated [2]rotaxane into a [4]catenane cyclic porphyrin hexamer in 62% yield, via palladium-catalysed Glaser coupling. The related [7]catenane porphyrin dodecamer complex was also isolated as a by-product of this cyclisation, in 6% yield. These results illustrate the scope of template-directed synthesis for creating complex interlocked structures directly from simple starting materials. © The Royal Society of Chemistry 2011. |
| spellingShingle | Langton, M Matichak, J Thompson, A Anderson, H Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title | Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title_full | Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title_fullStr | Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title_full_unstemmed | Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title_short | Template-directed synthesis of pi-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring |
| title_sort | template directed synthesis of pi conjugated porphyrin 2 rotaxanes and a 4 catenane based on a six porphyrin nanoring |
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