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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...

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Autores principales: Shi, Qixun, Javorskis, Tomas, Bergquist, Karl-Erik, Ulčinas, Artūras, Niaura, Gediminas, Matulaitienė, Ieva, Orentas, Edvinas, Wärnmark, Kenneth
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
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.
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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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