N-Hydroxysuccinimide-activated esters as a functionalization agent for amino cellulose: synthesis and solid-state NMR characterization
| Autor: | Jonas Lins, Markus Biesalski, Pedro Mendes, Pedro B. Groszewicz, Gerd Buntkowsky, Bharti Kumari, Torsten Gutmann |
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| Rok vydání: | 2019 |
| Předmět: |
Polymers and Plastics
02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry 0104 chemical sciences Microcrystalline cellulose chemistry.chemical_compound chemistry Solid-state nuclear magnetic resonance Diamine Benzophenone Surface modification Peptide bond Cellulose 0210 nano-technology Linker |
| Zdroj: | Cellulose. 27:1239-1254 |
| ISSN: | 1572-882X 0969-0239 |
| DOI: | 10.1007/s10570-019-02864-5 |
| Popis: | We propose a mild and versatile synthesis protocol based on N-hydroxysuccinimide-activated esters for the introduction of new functionalities to cellulose, using as starting point established protocols for the tosylation of cellulose and its subsequent reaction with a diamine linker. As a proof of concept, we describe the functionalization of microcrystalline cellulose with a N-hydroxysuccinimide-activated ester of benzophenone, a photoreactive functional group. Irradiation of the final product with UV light yields a self-standing polymer film and is expected to result in cross-linking among cellulose chains. To monitor structural changes at the molecular level, each functionalization step is characterized by a multinuclear solid-state NMR approach. DNP-enhanced 15N CP MAS NMR experiments reveal the formation of the amide bond to the photoreactive linker and deliver further information about the binding situation of nitrogen-containing groups in these materials. The flexible synthesis protocol described here can be easily extended to a broad range of other functionalities of interest, both for the cellulose and macromolecular research. |
| Databáze: | OpenAIRE |
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