Dendritic architectures by orthogonal thiol-maleimide 'click' and furan-maleimide dynamic covalent chemistries
| Autor: | Stephen H. Frayne, Brian H. Northrop, Robert M. Stolz |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Alkene Organic Chemistry 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Biochemistry Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound Monomer chemistry Covalent bond Furan Dendrimer Thiol Physical and Theoretical Chemistry 0210 nano-technology Maleimide |
| Zdroj: | Organic & Biomolecular Chemistry. 17:7878-7883 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c9ob01459d |
| Popis: | A set of dendrons and dendrimers is synthesized divergently using an orthogonal combination of kinetically-driven thiol-maleimide "click" chemistry and thermodynamically reversible furan-maleimide cycloaddition/retrocycloaddition reactions. Growth is controlled by taking advantage of the selective thiol-ene addition of thiols to the electron withdrawn alkene of maleimide in the presence of electron rich alkene of oxanorbornene. Subsequent activation of growing dendrons/dendrimers requires only heat to induce the dynamic covalent liberation of peripheral furan protecting groups. The methodology introduced provides a new route to multifunctional dendrimers that could, in principle, be synthesized by introducing different branched monomers at any stage of dendrimer growth, allowing dendrimer architectures and properties to be better tailored to their intended applications. |
| Databáze: | OpenAIRE |
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