Abstract
We develop the first method for catalytic, exhaustive ortho-alkoxylation of azobenzene photoswitches. Alkoxylation is known to improve the photoswitch properties that control azobenzenes' success in chemical biology or materials sciences, e.g., better completeness of both E-* Z and Z-* E photoisomerizations and >100 nm red shift of photoresponse. Our method enables straightforward late-stage diversification of photoswitches with interesting functional handles. We showcase four applications: using it to rationally tune lipophilicity, prepare isotopic tracers for metabolism studies, install full water solubility without ionic charges, and efficiently access previously difficult mixed-substituent photo switches. We also identified a previously unexplored mixedsubstituent tetra-ortho family, difluoro-dialkoxy-azobenzenes, whose photoresponse can outperform previous 'gold standard' tetrafluoro-, dichloro-difluoro-, and tetrachloro-azobenzenes in significant ways. We thus expect that both the scaffolds we showcase and the method we develop will impact broadly on photochemistry and photopharmacology.
| Dokumententyp: | Zeitschriftenartikel |
|---|---|
| Fakultät: | Chemie und Pharmazie > Department für Pharmazie - Zentrum für Pharmaforschung |
| Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| ISSN: | 0022-3263 |
| Sprache: | Englisch |
| Dokumenten ID: | 111293 |
| Datum der Veröffentlichung auf Open Access LMU: | 02. Apr. 2024, 07:24 |
| Letzte Änderungen: | 02. Apr. 2024, 07:24 |
| DFG: | Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 201269156 |
| DFG: | Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 239283807 |
| DFG: | Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 400324123 |
| DFG: | Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 426018126 |
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