Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage

The synthesis of a new porous organic cage decorated with isopropyl moieties (CC21) was achieved from the reaction of triformylbenzene and an isopropyl functionalised diamine. Unlike structurally analogous porous organic cages, its synthesis proved challenging due to competitive aminal formation, ra...

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Detalles Bibliográficos
Autores principales: Kearsey, Rachel J., Tarzia, Andrew, Little, Marc A., Brand, Michael C., Clowes, Rob, Jelfs, Kim E., Cooper, Andrew I., Greenaway, Rebecca L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10035065/
https://www.ncbi.nlm.nih.gov/pubmed/36896582
http://dx.doi.org/10.1039/d3cc00072a
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author Kearsey, Rachel J.
Tarzia, Andrew
Little, Marc A.
Brand, Michael C.
Clowes, Rob
Jelfs, Kim E.
Cooper, Andrew I.
Greenaway, Rebecca L.
author_facet Kearsey, Rachel J.
Tarzia, Andrew
Little, Marc A.
Brand, Michael C.
Clowes, Rob
Jelfs, Kim E.
Cooper, Andrew I.
Greenaway, Rebecca L.
author_sort Kearsey, Rachel J.
collection PubMed
description The synthesis of a new porous organic cage decorated with isopropyl moieties (CC21) was achieved from the reaction of triformylbenzene and an isopropyl functionalised diamine. Unlike structurally analogous porous organic cages, its synthesis proved challenging due to competitive aminal formation, rationalised using control experiments and computational modelling. The use of an additional amine was found to increase conversion to the desired cage.
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spelling pubmed-100350652023-03-24 Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage Kearsey, Rachel J. Tarzia, Andrew Little, Marc A. Brand, Michael C. Clowes, Rob Jelfs, Kim E. Cooper, Andrew I. Greenaway, Rebecca L. Chem Commun (Camb) Chemistry The synthesis of a new porous organic cage decorated with isopropyl moieties (CC21) was achieved from the reaction of triformylbenzene and an isopropyl functionalised diamine. Unlike structurally analogous porous organic cages, its synthesis proved challenging due to competitive aminal formation, rationalised using control experiments and computational modelling. The use of an additional amine was found to increase conversion to the desired cage. The Royal Society of Chemistry 2023-02-23 /pmc/articles/PMC10035065/ /pubmed/36896582 http://dx.doi.org/10.1039/d3cc00072a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Kearsey, Rachel J.
Tarzia, Andrew
Little, Marc A.
Brand, Michael C.
Clowes, Rob
Jelfs, Kim E.
Cooper, Andrew I.
Greenaway, Rebecca L.
Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title_full Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title_fullStr Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title_full_unstemmed Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title_short Competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
title_sort competitive aminal formation during the synthesis of a highly soluble, isopropyl-decorated imine porous organic cage
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10035065/
https://www.ncbi.nlm.nih.gov/pubmed/36896582
http://dx.doi.org/10.1039/d3cc00072a
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