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Facile synthesis of oligoyne amphiphiles and their rotaxanes

Carbon-rich organic compounds containing a series of conjugated triple bonds (oligoynes) are relevant synthetic targets, but an improved access to oligoynes bearing functional groups would be desirable. Here, we report the straightforward synthesis of two series of oligoyne amphiphiles with glycosid...

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Autores principales: Schrettl, Stephen, Contal, Emmanuel, Hoheisel, Tobias N., Fritzsche, Martin, Balog, Sandor, Szilluweit, Ruth, Frauenrath, Holger
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5492104/
https://www.ncbi.nlm.nih.gov/pubmed/28706625
http://dx.doi.org/10.1039/c4sc03154g
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author Schrettl, Stephen
Contal, Emmanuel
Hoheisel, Tobias N.
Fritzsche, Martin
Balog, Sandor
Szilluweit, Ruth
Frauenrath, Holger
author_facet Schrettl, Stephen
Contal, Emmanuel
Hoheisel, Tobias N.
Fritzsche, Martin
Balog, Sandor
Szilluweit, Ruth
Frauenrath, Holger
author_sort Schrettl, Stephen
collection PubMed
description Carbon-rich organic compounds containing a series of conjugated triple bonds (oligoynes) are relevant synthetic targets, but an improved access to oligoynes bearing functional groups would be desirable. Here, we report the straightforward synthesis of two series of oligoyne amphiphiles with glycoside or carboxylate polar head groups, investigate their self-assembly behavior in aqueous media, and their use as precursors for the formation of oligoyne rotaxanes with cyclodextrin hosts. To this end, we employed mono-, di-, or triacetylenic building blocks that gave access to the corresponding zinc acetylides in situ and allowed for the efficient elongation of the oligoyne segment in few synthetic steps via a Negishi coupling protocol. Moreover, we show that the obtained oligoyne derivatives can be deprotected to yield the corresponding amphiphiles. Depending on their head groups, the supramolecular self-assembly of these amphiphiles gave rise to different types of carbon-rich colloidal aggregates in aqueous media. Furthermore, their amphiphilicity was exploited for the preparation of novel oligoyne cyclodextrin rotaxanes using simple host–guest chemistry in water.
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spelling pubmed-54921042017-07-13 Facile synthesis of oligoyne amphiphiles and their rotaxanes Schrettl, Stephen Contal, Emmanuel Hoheisel, Tobias N. Fritzsche, Martin Balog, Sandor Szilluweit, Ruth Frauenrath, Holger Chem Sci Chemistry Carbon-rich organic compounds containing a series of conjugated triple bonds (oligoynes) are relevant synthetic targets, but an improved access to oligoynes bearing functional groups would be desirable. Here, we report the straightforward synthesis of two series of oligoyne amphiphiles with glycoside or carboxylate polar head groups, investigate their self-assembly behavior in aqueous media, and their use as precursors for the formation of oligoyne rotaxanes with cyclodextrin hosts. To this end, we employed mono-, di-, or triacetylenic building blocks that gave access to the corresponding zinc acetylides in situ and allowed for the efficient elongation of the oligoyne segment in few synthetic steps via a Negishi coupling protocol. Moreover, we show that the obtained oligoyne derivatives can be deprotected to yield the corresponding amphiphiles. Depending on their head groups, the supramolecular self-assembly of these amphiphiles gave rise to different types of carbon-rich colloidal aggregates in aqueous media. Furthermore, their amphiphilicity was exploited for the preparation of novel oligoyne cyclodextrin rotaxanes using simple host–guest chemistry in water. Royal Society of Chemistry 2015-01-01 2014-10-24 /pmc/articles/PMC5492104/ /pubmed/28706625 http://dx.doi.org/10.1039/c4sc03154g Text en This journal is © The Royal Society of Chemistry 2014 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Schrettl, Stephen
Contal, Emmanuel
Hoheisel, Tobias N.
Fritzsche, Martin
Balog, Sandor
Szilluweit, Ruth
Frauenrath, Holger
Facile synthesis of oligoyne amphiphiles and their rotaxanes
title Facile synthesis of oligoyne amphiphiles and their rotaxanes
title_full Facile synthesis of oligoyne amphiphiles and their rotaxanes
title_fullStr Facile synthesis of oligoyne amphiphiles and their rotaxanes
title_full_unstemmed Facile synthesis of oligoyne amphiphiles and their rotaxanes
title_short Facile synthesis of oligoyne amphiphiles and their rotaxanes
title_sort facile synthesis of oligoyne amphiphiles and their rotaxanes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5492104/
https://www.ncbi.nlm.nih.gov/pubmed/28706625
http://dx.doi.org/10.1039/c4sc03154g
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