Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives
Abstract The introduction of a chemical additive to supramolecular polymers holds high potential in the development of new structures and functions. In this regard, various donor- and acceptor-based molecules have been applied in the design of these noncovalent polymers. However, the incorporation o...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag
2021-04-01
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| Series: | Organic Materials |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1727235 |
| _version_ | 1830483530232102912 |
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| author | P. Chidchob S. A. H. Jansen S. C. J. Meskers E. Weyandt N. P. van Leest B. de Bruin A. R. A. Palmans G. Vantomme E. W. Meijer |
| author_facet | P. Chidchob S. A. H. Jansen S. C. J. Meskers E. Weyandt N. P. van Leest B. de Bruin A. R. A. Palmans G. Vantomme E. W. Meijer |
| author_sort | P. Chidchob |
| collection | DOAJ |
| description | Abstract
The introduction of a chemical additive to supramolecular polymers holds high potential in the development of new structures and functions. In this regard, various donor- and acceptor-based molecules have been applied in the design of these noncovalent polymers. However, the incorporation of boron–nitrogen frustrated Lewis pairs in such architectures is still rare despite their many intriguing properties in catalysis and materials science. The limited choices of suitable boron derivatives represent one of the main limitations for the advancement in this direction. Here, we examine the use of the commercially available tris(pentafluorophenyl)borane with various triphenylamine derivatives to create supramolecular B–N charge transfer systems. Our results highlight the importance of a proper balance between the donor/acceptor strength and the driving force for supramolecular polymerization to achieve stable, long-range ordered B–N systems. Detailed analyses using electron paramagnetic resonance and optical spectroscopy suggest that tris(pentafluorophenyl)borane displays complex behavior with the amide-based triphenylamine supramolecular polymers and may interact in dimers or larger chiral aggregates, depending on the specific structure of the triphenylamines. |
| first_indexed | 2024-12-21T17:53:43Z |
| format | Article |
| id | doaj.art-3ca11611a5ca4673a70b65e1e9787d39 |
| institution | Directory Open Access Journal |
| issn | 2625-1825 |
| language | English |
| last_indexed | 2024-12-21T17:53:43Z |
| publishDate | 2021-04-01 |
| publisher | Georg Thieme Verlag |
| record_format | Article |
| series | Organic Materials |
| spelling | doaj.art-3ca11611a5ca4673a70b65e1e9787d392022-12-21T18:55:16ZengGeorg Thieme VerlagOrganic Materials2625-18252021-04-01030217418310.1055/s-0041-1727235Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine DerivativesP. Chidchob0S. A. H. Jansen1S. C. J. Meskers2E. Weyandt3N. P. van Leest4B. de Bruin5A. R. A. Palmans6G. Vantomme7E. W. Meijer8Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsHomogeneous, Supramolecular and Bio-Inspired Catalysis Group, van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The NetherlandsHomogeneous, Supramolecular and Bio-Inspired Catalysis Group, van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsLaboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The NetherlandsAbstract The introduction of a chemical additive to supramolecular polymers holds high potential in the development of new structures and functions. In this regard, various donor- and acceptor-based molecules have been applied in the design of these noncovalent polymers. However, the incorporation of boron–nitrogen frustrated Lewis pairs in such architectures is still rare despite their many intriguing properties in catalysis and materials science. The limited choices of suitable boron derivatives represent one of the main limitations for the advancement in this direction. Here, we examine the use of the commercially available tris(pentafluorophenyl)borane with various triphenylamine derivatives to create supramolecular B–N charge transfer systems. Our results highlight the importance of a proper balance between the donor/acceptor strength and the driving force for supramolecular polymerization to achieve stable, long-range ordered B–N systems. Detailed analyses using electron paramagnetic resonance and optical spectroscopy suggest that tris(pentafluorophenyl)borane displays complex behavior with the amide-based triphenylamine supramolecular polymers and may interact in dimers or larger chiral aggregates, depending on the specific structure of the triphenylamines.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1727235supramolecular assemblytris(pentafluorophenyl)boranetriphenylaminecharge transfer |
| spellingShingle | P. Chidchob S. A. H. Jansen S. C. J. Meskers E. Weyandt N. P. van Leest B. de Bruin A. R. A. Palmans G. Vantomme E. W. Meijer Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives Organic Materials supramolecular assembly tris(pentafluorophenyl)borane triphenylamine charge transfer |
| title | Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives |
| title_full | Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives |
| title_fullStr | Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives |
| title_full_unstemmed | Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives |
| title_short | Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives |
| title_sort | supramolecular systems containing b n frustrated lewis pairs of tris pentafluorophenyl borane and triphenylamine derivatives |
| topic | supramolecular assembly tris(pentafluorophenyl)borane triphenylamine charge transfer |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1727235 |
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