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Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer
The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C(2)-symmetric enantiopure bicyclic cavity comp...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5394284/ https://www.ncbi.nlm.nih.gov/pubmed/28401927 http://dx.doi.org/10.1038/ncomms14943 |
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author | Shi, Qixun Javorskis, Tomas Bergquist, Karl-Erik Ulčinas, Artūras Niaura, Gediminas Matulaitienė, Ieva Orentas, Edvinas Wärnmark, Kenneth |
author_facet | Shi, Qixun Javorskis, Tomas Bergquist, Karl-Erik Ulčinas, Artūras Niaura, Gediminas Matulaitienė, Ieva Orentas, Edvinas Wärnmark, Kenneth |
author_sort | Shi, Qixun |
collection | PubMed |
description | The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C(2)-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C(60) and C(70) guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C(70) guests, further aggregation into tubular supramolecular polymers is achieved. The open-end cyclic assemblies rearrange into a closed-shell capsule upon introduction of C(60) with an accompanied symmetry breaking of the monomer. Our study demonstrates that a C(60) switch can be used to simultaneously control the topology and occupancy of tubular assemblies resulting from the aggregation of small monomers. |
format | Online Article Text |
id | pubmed-5394284 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-53942842017-05-17 Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer Shi, Qixun Javorskis, Tomas Bergquist, Karl-Erik Ulčinas, Artūras Niaura, Gediminas Matulaitienė, Ieva Orentas, Edvinas Wärnmark, Kenneth Nat Commun Article The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C(2)-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C(60) and C(70) guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C(70) guests, further aggregation into tubular supramolecular polymers is achieved. The open-end cyclic assemblies rearrange into a closed-shell capsule upon introduction of C(60) with an accompanied symmetry breaking of the monomer. Our study demonstrates that a C(60) switch can be used to simultaneously control the topology and occupancy of tubular assemblies resulting from the aggregation of small monomers. Nature Publishing Group 2017-04-12 /pmc/articles/PMC5394284/ /pubmed/28401927 http://dx.doi.org/10.1038/ncomms14943 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Shi, Qixun Javorskis, Tomas Bergquist, Karl-Erik Ulčinas, Artūras Niaura, Gediminas Matulaitienė, Ieva Orentas, Edvinas Wärnmark, Kenneth Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title | Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title_full | Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title_fullStr | Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title_full_unstemmed | Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title_short | Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
title_sort | stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5394284/ https://www.ncbi.nlm.nih.gov/pubmed/28401927 http://dx.doi.org/10.1038/ncomms14943 |
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