Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Sandra MC Schoenmakers
- Bart WL van den Bersselaar
- Shikha Dhiman
- Lu Su
- Anja RA Palmans
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000695624800001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1039/d1ob01587g
- eISSN
- 1477-0539
- Externe Identifier
- Clarivate Analytics Document Solution ID: WC8GW
- PubMed Identifier: 34518862
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 38
- Zeitschrift
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Paginierung
- 8281 - 8294
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Titel
- Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity
- Sub types
- Article
- Ausgabe der Zeitschrift
- 19
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:p>Selective functionalization of <jats:italic>C</jats:italic><jats:sub>3</jats:sub>-symmetrical supramolecular motifs was achieved by switching the amide connectivity of one side chain, yielding supramolecular polymers with a tunable number of functional groups.</jats:p>
- Autoren
- Sandra MC Schoenmakers
- Bart WL van den Bersselaar
- Shikha Dhiman
- Lu Su
- Anja RA Palmans
- DOI
- 10.1039/d1ob01587g
- eISSN
- 1477-0539
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 38
- Zeitschrift
- Organic & Biomolecular Chemistry
- Sprache
- en
- Online publication date
- 2021
- Paginierung
- 8281 - 8294
- Status
- Published online
- Herausgeber
- Royal Society of Chemistry (RSC)
- Herausgeber URL
- http://dx.doi.org/10.1039/d1ob01587g
- Datum der Datenerfassung
- 2024
- Titel
- Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity
- Ausgabe der Zeitschrift
- 19
Datenquelle: Crossref
- Abstract
- Synthetic water-compatible supramolecular polymers based on benzene-1,3,5-tricarboxamides (BTAs) have attracted a lot of interest in recent years, as they are uniquely suited to generate functional multicomponent biomaterials. Their morphologies and intrinsic dynamic behaviour mimic fibrous structures found in nature. Moreover, their modularity allows control of the density of functionalities presented on the surface of the fibres when using functionalized BTA monomers. However, such moieties generally comprise a functionality on only one of three side chains, resulting in lengthy synthetic protocols and limited yields. In this work, we avert the need for desymmetrization of the core by starting from commercially available 5-aminoisophthalic acid. This approach eliminates the statistical reactions and reduces the number of synthetic steps. It also leads to the inversion of the connectivity of one of the amides to the benzene core. By combining spectroscopy, light scattering and cryogenic transmission electron microscopy, we confirm that the inversed amide BTAs (iBTAs) form intermolecular hydrogen bonds and assemble into supramolecular polymers, like previously used symmetrical BTAs, albeit with a slight decrease in water solubility. Solubility problems were overcome by incorporating iBTAs into conventional BTA-based supramolecular polymers. These two-component mixtures formed supramolecular fibres with a morphology and dynamic behaviour similar to BTA-homopolymers. Finally, iBTAs were decorated with a fluorescent dye to demonstrate the synthesis of functional monomers, and to visualize their co-assembly with BTAs. Our results show that functionality can be introduced into supramolecular polymers with monomers that slightly differ in their core structure while maintaining the structure and dynamics of the fibres.
- Addresses
- Laboratory of Macromolecular and Organic Chemistry, Institute for Complex Molecular Systems, Eindhoven University of Technology, Eindhoven, The Netherlands. a.palmans@tue.nl.
- Autoren
- Sandra MC Schoenmakers
- Bart WL van den Bersselaar
- Shikha Dhiman
- Lu Su
- Anja RA Palmans
- DOI
- 10.1039/d1ob01587g
- eISSN
- 1477-0539
- Externe Identifier
- PubMed Identifier: 34518862
- PubMed Central ID: PMC8494077
- Funding acknowledgements
- European Research Council: H2020-EU.1.1.
- European Research Council: 788618
- European Research Council: ID 788618
- European Research Council: SYNMAT project
- European Research Council:
- Ministerie van Onderwijs, Cultuur en Wetenschap:
- Open access
- true
- ISSN
- 1477-0520
- Ausgabe der Veröffentlichung
- 38
- Zeitschrift
- Organic & biomolecular chemistry
- Sprache
- eng
- Medium
- Electronic
- Online publication date
- 2021
- Open access status
- Open Access
- Paginierung
- 8281 - 8294
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Publisher licence
- CC BY-NC
- Datum der Datenerfassung
- 2021
- Titel
- Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity.
- Sub types
- Research Support, Non-U.S. Gov't
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 19
Datenquelle: Europe PubMed Central
- Abstract
- Synthetic water-compatible supramolecular polymers based on benzene-1,3,5-tricarboxamides (BTAs) have attracted a lot of interest in recent years, as they are uniquely suited to generate functional multicomponent biomaterials. Their morphologies and intrinsic dynamic behaviour mimic fibrous structures found in nature. Moreover, their modularity allows control of the density of functionalities presented on the surface of the fibres when using functionalized BTA monomers. However, such moieties generally comprise a functionality on only one of three side chains, resulting in lengthy synthetic protocols and limited yields. In this work, we avert the need for desymmetrization of the core by starting from commercially available 5-aminoisophthalic acid. This approach eliminates the statistical reactions and reduces the number of synthetic steps. It also leads to the inversion of the connectivity of one of the amides to the benzene core. By combining spectroscopy, light scattering and cryogenic transmission electron microscopy, we confirm that the inversed amide BTAs (iBTAs) form intermolecular hydrogen bonds and assemble into supramolecular polymers, like previously used symmetrical BTAs, albeit with a slight decrease in water solubility. Solubility problems were overcome by incorporating iBTAs into conventional BTA-based supramolecular polymers. These two-component mixtures formed supramolecular fibres with a morphology and dynamic behaviour similar to BTA-homopolymers. Finally, iBTAs were decorated with a fluorescent dye to demonstrate the synthesis of functional monomers, and to visualize their co-assembly with BTAs. Our results show that functionality can be introduced into supramolecular polymers with monomers that slightly differ in their core structure while maintaining the structure and dynamics of the fibres.
- Autoren
- Sandra MC Schoenmakers
- Bart WL van den Bersselaar
- Shikha Dhiman
- Lu Su
- Anja RA Palmans
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/34518862
- DOI
- 10.1039/d1ob01587g
- eISSN
- 1477-0539
- Externe Identifier
- PubMed Central ID: PMC8494077
- Funding acknowledgements
- European Research Council:
- Ausgabe der Veröffentlichung
- 38
- Zeitschrift
- Org Biomol Chem
- Sprache
- eng
- Country
- England
- Paginierung
- 8281 - 8294
- Datum der Veröffentlichung
- 2021
- Status
- Published online
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Titel
- Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 19
Datenquelle: PubMed
- Beziehungen:
-