Cargando…

Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages

One of the most applied reaction types to synthesize shape‐persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine condensation. However, most of the synthesized imine...

Descripción completa

Detalles Bibliográficos
Autores principales: Holsten, Mattes, Feierabend, Sarah, Elbert, Sven M., Rominger, Frank, Oeser, Thomas, Mastalerz, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362185/
https://www.ncbi.nlm.nih.gov/pubmed/33848032
http://dx.doi.org/10.1002/chem.202100666
_version_ 1783738109026893824
author Holsten, Mattes
Feierabend, Sarah
Elbert, Sven M.
Rominger, Frank
Oeser, Thomas
Mastalerz, Michael
author_facet Holsten, Mattes
Feierabend, Sarah
Elbert, Sven M.
Rominger, Frank
Oeser, Thomas
Mastalerz, Michael
author_sort Holsten, Mattes
collection PubMed
description One of the most applied reaction types to synthesize shape‐persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine condensation. However, most of the synthesized imine cages reported are formed as precipitate from the reaction mixture and therefore rather may be kinetically controlled products. There are even examples in literature, where resulting cages are not soluble at all in common organic solvents to characterize or study their formation by NMR spectroscopy in solution. Here, a triptycene triamine containing three solubilizing n‐hexyloxy chains has been used to synthesize soluble congeners of prior insoluble cages. This allowed us to study the formation as well as the reversibility of cage formation in solution by investigating exchange of building blocks between the cages and deuterated derivatives thereof.
format Online
Article
Text
id pubmed-8362185
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-83621852021-08-17 Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages Holsten, Mattes Feierabend, Sarah Elbert, Sven M. Rominger, Frank Oeser, Thomas Mastalerz, Michael Chemistry Full Papers One of the most applied reaction types to synthesize shape‐persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine condensation. However, most of the synthesized imine cages reported are formed as precipitate from the reaction mixture and therefore rather may be kinetically controlled products. There are even examples in literature, where resulting cages are not soluble at all in common organic solvents to characterize or study their formation by NMR spectroscopy in solution. Here, a triptycene triamine containing three solubilizing n‐hexyloxy chains has been used to synthesize soluble congeners of prior insoluble cages. This allowed us to study the formation as well as the reversibility of cage formation in solution by investigating exchange of building blocks between the cages and deuterated derivatives thereof. John Wiley and Sons Inc. 2021-05-24 2021-06-25 /pmc/articles/PMC8362185/ /pubmed/33848032 http://dx.doi.org/10.1002/chem.202100666 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://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
Holsten, Mattes
Feierabend, Sarah
Elbert, Sven M.
Rominger, Frank
Oeser, Thomas
Mastalerz, Michael
Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title_full Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title_fullStr Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title_full_unstemmed Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title_short Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages
title_sort soluble congeners of prior insoluble shape‐persistent imine cages
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362185/
https://www.ncbi.nlm.nih.gov/pubmed/33848032
http://dx.doi.org/10.1002/chem.202100666
work_keys_str_mv AT holstenmattes solublecongenersofpriorinsolubleshapepersistentiminecages
AT feierabendsarah solublecongenersofpriorinsolubleshapepersistentiminecages
AT elbertsvenm solublecongenersofpriorinsolubleshapepersistentiminecages
AT romingerfrank solublecongenersofpriorinsolubleshapepersistentiminecages
AT oeserthomas solublecongenersofpriorinsolubleshapepersistentiminecages
AT mastalerzmichael solublecongenersofpriorinsolubleshapepersistentiminecages