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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...

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Autores principales: Pérez‐Ojeda, M. Eugenia, Wabra, Isabell, Böttcher, Christoph, Hirsch, Andreas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
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.
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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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