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Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly
Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The sy...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6585616/ https://www.ncbi.nlm.nih.gov/pubmed/30058727 http://dx.doi.org/10.1002/chem.201803036 |
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author | Pérez‐Ojeda, M. Eugenia Wabra, Isabell Böttcher, Christoph Hirsch, Andreas |
author_facet | Pérez‐Ojeda, M. Eugenia Wabra, Isabell Böttcher, Christoph Hirsch, Andreas |
author_sort | Pérez‐Ojeda, M. Eugenia |
collection | PubMed |
description | Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo‐TEM. |
format | Online Article Text |
id | pubmed-6585616 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-65856162019-06-27 Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly Pérez‐Ojeda, M. Eugenia Wabra, Isabell Böttcher, Christoph Hirsch, Andreas Chemistry Full Papers Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo‐TEM. John Wiley and Sons Inc. 2018-09-13 2018-09-20 /pmc/articles/PMC6585616/ /pubmed/30058727 http://dx.doi.org/10.1002/chem.201803036 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Pérez‐Ojeda, M. Eugenia Wabra, Isabell Böttcher, Christoph Hirsch, Andreas Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title | Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title_full | Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title_fullStr | Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title_full_unstemmed | Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title_short | Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly |
title_sort | fullerene building blocks with tailor‐made solubility and new insights into their hierarchical self‐assembly |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6585616/ https://www.ncbi.nlm.nih.gov/pubmed/30058727 http://dx.doi.org/10.1002/chem.201803036 |
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