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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...

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Autores principales: Liu, Pengpeng, Neuhaus, Patrik, Kondratuk, Dmitry V, Balaban, T Silviu, Anderson, Harry L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
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.
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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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