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Cyclodextrin-Templated Porphyrin Nanorings**
α- and β-Cyclodextrins have been used as scaffolds for the synthesis of six- and seven-legged templates by functionalizing every primary CH(2)OH with a 4-pyridyl moiety. Although these templates are flexible, they are very effective for directing the synthesis of macrocyclic porphyrin oligomers cons...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
WILEY-VCH Verlag
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4298808/ https://www.ncbi.nlm.nih.gov/pubmed/24916813 http://dx.doi.org/10.1002/anie.201402917 |
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author | Liu, Pengpeng Neuhaus, Patrik Kondratuk, Dmitry V Balaban, T Silviu Anderson, Harry L |
author_facet | Liu, Pengpeng Neuhaus, Patrik Kondratuk, Dmitry V Balaban, T Silviu Anderson, Harry L |
author_sort | Liu, Pengpeng |
collection | PubMed |
description | α- and β-Cyclodextrins have been used as scaffolds for the synthesis of six- and seven-legged templates by functionalizing every primary CH(2)OH with a 4-pyridyl moiety. Although these templates are flexible, they are very effective for directing the synthesis of macrocyclic porphyrin oligomers consisting of six or seven porphyrin units. The transfer of chirality from the cyclodextrin templates to their nanoring hosts is evident from NMR and circular dichroism spectroscopy. Surprisingly, the mean effective molarity for binding the flexible α-cyclodextrin-based template within the six-porphyrin nanoring (74 m) is almost as high as for the previously studied rigid hexadentate template (180 m). The discovery that flexible templates are effective in this system, and the availability of a template with a prime number of binding sites, open up many possibilities for the template-directed synthesis of larger macrocycles. |
format | Online Article Text |
id | pubmed-4298808 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | WILEY-VCH Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-42988082015-01-27 Cyclodextrin-Templated Porphyrin Nanorings** Liu, Pengpeng Neuhaus, Patrik Kondratuk, Dmitry V Balaban, T Silviu Anderson, Harry L Angew Chem Int Ed Engl Communications α- and β-Cyclodextrins have been used as scaffolds for the synthesis of six- and seven-legged templates by functionalizing every primary CH(2)OH with a 4-pyridyl moiety. Although these templates are flexible, they are very effective for directing the synthesis of macrocyclic porphyrin oligomers consisting of six or seven porphyrin units. The transfer of chirality from the cyclodextrin templates to their nanoring hosts is evident from NMR and circular dichroism spectroscopy. Surprisingly, the mean effective molarity for binding the flexible α-cyclodextrin-based template within the six-porphyrin nanoring (74 m) is almost as high as for the previously studied rigid hexadentate template (180 m). The discovery that flexible templates are effective in this system, and the availability of a template with a prime number of binding sites, open up many possibilities for the template-directed synthesis of larger macrocycles. WILEY-VCH Verlag 2014-07-21 2014-06-10 /pmc/articles/PMC4298808/ /pubmed/24916813 http://dx.doi.org/10.1002/anie.201402917 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited https://creativecommons.org/licenses/by/4.0/ © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited |
spellingShingle | Communications Liu, Pengpeng Neuhaus, Patrik Kondratuk, Dmitry V Balaban, T Silviu Anderson, Harry L Cyclodextrin-Templated Porphyrin Nanorings** |
title | Cyclodextrin-Templated Porphyrin Nanorings** |
title_full | Cyclodextrin-Templated Porphyrin Nanorings** |
title_fullStr | Cyclodextrin-Templated Porphyrin Nanorings** |
title_full_unstemmed | Cyclodextrin-Templated Porphyrin Nanorings** |
title_short | Cyclodextrin-Templated Porphyrin Nanorings** |
title_sort | cyclodextrin-templated porphyrin nanorings** |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4298808/ https://www.ncbi.nlm.nih.gov/pubmed/24916813 http://dx.doi.org/10.1002/anie.201402917 |
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