Covalent template-directed synthesis of a spoked 18-porphyrin nanoring
Rings of porphyrins mimic natural light-harvesting chlorophyll arrays and provide insights into electronic delocalization, providing a motivation for creating larger nanorings with closely spaced porphyrin units. Here, we demonstrate the first synthesis of a macrocycle consisting entirely of 5,15-li...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2023
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| _version_ | 1826310045601628160 |
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| author | Majewski, M Stawski, W Van Raden, J Clarke, M Hart, J O'Shea, J Saywell, A Anderson, HL |
| author_facet | Majewski, M Stawski, W Van Raden, J Clarke, M Hart, J O'Shea, J Saywell, A Anderson, HL |
| author_sort | Majewski, M |
| collection | OXFORD |
| description | Rings of porphyrins mimic natural light-harvesting chlorophyll arrays and provide insights into electronic delocalization, providing a motivation for creating larger nanorings with closely spaced porphyrin units. Here, we demonstrate the first synthesis of a macrocycle consisting entirely of 5,15-linked porphyrins. This porphyrin octadecamer was constructed using a covalent six-armed template, made by cobalt-catalyzed cyclotrimerization of an H-shaped tolan with porphyrin trimer ends. The porphyrins around the circumference of the nanoring were linked together by intramolecular oxidative meso-meso coupling and partial β-β fusion, to give a nanoring consisting of six edge-fused zinc(II) porphyrin dimer units and six un-fused nickel(II) porphyrins. STM imaging on a gold surface confirms the size and shape of the spoked 18-porphyrin nanoring (calculated diameter: 4.7 nm). |
| first_indexed | 2024-03-07T07:44:42Z |
| format | Journal article |
| id | oxford-uuid:ede76f20-e5e6-491c-935c-f83dc21ea7e6 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:44:42Z |
| publishDate | 2023 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:ede76f20-e5e6-491c-935c-f83dc21ea7e62023-05-22T15:30:08ZCovalent template-directed synthesis of a spoked 18-porphyrin nanoringJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ede76f20-e5e6-491c-935c-f83dc21ea7e6EnglishSymplectic ElementsWiley2023Majewski, MStawski, WVan Raden, JClarke, MHart, JO'Shea, JSaywell, AAnderson, HLRings of porphyrins mimic natural light-harvesting chlorophyll arrays and provide insights into electronic delocalization, providing a motivation for creating larger nanorings with closely spaced porphyrin units. Here, we demonstrate the first synthesis of a macrocycle consisting entirely of 5,15-linked porphyrins. This porphyrin octadecamer was constructed using a covalent six-armed template, made by cobalt-catalyzed cyclotrimerization of an H-shaped tolan with porphyrin trimer ends. The porphyrins around the circumference of the nanoring were linked together by intramolecular oxidative meso-meso coupling and partial β-β fusion, to give a nanoring consisting of six edge-fused zinc(II) porphyrin dimer units and six un-fused nickel(II) porphyrins. STM imaging on a gold surface confirms the size and shape of the spoked 18-porphyrin nanoring (calculated diameter: 4.7 nm). |
| spellingShingle | Majewski, M Stawski, W Van Raden, J Clarke, M Hart, J O'Shea, J Saywell, A Anderson, HL Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title | Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title_full | Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title_fullStr | Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title_full_unstemmed | Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title_short | Covalent template-directed synthesis of a spoked 18-porphyrin nanoring |
| title_sort | covalent template directed synthesis of a spoked 18 porphyrin nanoring |
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