Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/5/1358 |
| _version_ | 1827603549923573760 |
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| author | Christina Wappl Viktor Schallert Christian Slugovc Astrid-Caroline Knall Stefan Spirk |
| author_facet | Christina Wappl Viktor Schallert Christian Slugovc Astrid-Caroline Knall Stefan Spirk |
| author_sort | Christina Wappl |
| collection | DOAJ |
| description | A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts. |
| first_indexed | 2024-03-09T05:41:14Z |
| format | Article |
| id | doaj.art-7ae57f455057460cb6c17345fb3de90a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:41:14Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7ae57f455057460cb6c17345fb3de90a2023-12-03T12:24:54ZengMDPI AGMolecules1420-30492021-03-01265135810.3390/molecules26051358Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) ReactionChristina Wappl0Viktor Schallert1Christian Slugovc2Astrid-Caroline Knall3Stefan Spirk4Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, AustriaInstitute of Bioproducts and Paper Technology, Graz University of Technology, Inffeldgasse 23A, 8010 Graz, AustriaA facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts.https://www.mdpi.com/1420-3049/26/5/1358celluloseclick chemistryiEDDAcopper-freenorbornene cellulosecellulose ester |
| spellingShingle | Christina Wappl Viktor Schallert Christian Slugovc Astrid-Caroline Knall Stefan Spirk Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction Molecules cellulose click chemistry iEDDA copper-free norbornene cellulose cellulose ester |
| title | Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction |
| title_full | Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction |
| title_fullStr | Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction |
| title_full_unstemmed | Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction |
| title_short | Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction |
| title_sort | highly norbornylated cellulose and its click modification by an inverse electron demand diels alder iedda reaction |
| topic | cellulose click chemistry iEDDA copper-free norbornene cellulose cellulose ester |
| url | https://www.mdpi.com/1420-3049/26/5/1358 |
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