0000000000328578
AUTHOR
Frank Rominger
Bioorthogonal red and far-red fluorogenic probes for wash-free live-cell and super-resolution microscopy
AbstractSmall-molecule fluorophores enable the observation of biomolecules in their native context with fluorescence microscopy. Specific labelling via bioorthogonal tetrazine chemistry confers minimal label size and rapid labelling kinetics. At the same time, fluorogenic tetrazine-dye conjugates exhibit efficient quenching of dyes prior to target binding. However, live-cell compatible long-wavelength fluorophores with strong fluorogenicity have been difficult to realize. Here, we report close proximity tetrazine-dye conjugates with minimal distance between tetrazine and fluorophore. Two synthetic routes give access to a series of cell permeable and impermeable dyes including highly fluorog…
Consequences of the One-Electron Reduction and Photoexcitation of Unsymmetric Bis-imidazolium Salts
Coupling of uronium salts with in situ generated N-heterocyclic carbenes provides straightforward access to symmetrical [4](2+) and unsymmetrical bis-imidazolium salts [6](2+) and [9](2+) . As indicated by cyclic and square-wave voltammetry, [6](2+) and [9](2+) can be (irreversibly) reduced by one electron. The initially formed radicals [6](.+) and [9](.+) undergo further reactions, which were probed by EPR spectroscopy and density functional calculations. The final products of the two-electron reduction are the two carbenes. Upon irradiation with UV light both [6](2+) and [9](2+) emit at room temperature in solution but with dramatically different characteristics. The different fluorescenc…
Microporous Triptycene‐Based Affinity Materials on Quartz Crystal Microbalances for Tracing of Illicit Compounds
Triptycene-based organic molecules of intrinsic microporosity (OMIMs) with extended functionalized π-surfaces are excellent materials for gas sorption and separation. In this study, the affinities of triptycene-based OMIM affinity materials on 195 MHz high-fundamental-frequency quartz crystal microbalances (HFF-QCMs) for hazardous and illicit compounds such as piperonal and (-)-norephedrine were determined. Both new and existing porous triptycene-based affinity materials were investigated, resulting in very high sensitivities and selectivities that could be applied for sensing purposes. Remarkable results were found for safrole - a starting material for illicit compounds such as ecstasy. A …
Bio-orthogonal Red and Far-Red Fluorogenic Probes for Wash-Free Live-Cell and Super-resolution Microscopy
Small-molecule fluorophores enable the observation of biomolecules in their native context with fluorescence microscopy. Specific labeling via bio-orthogonal tetrazine chemistry combines minimal label size with rapid labeling kinetics. At the same time, fluorogenic tetrazine–dye conjugates exhibit efficient quenching of dyes prior to target binding. However, live-cell compatible long-wavelength fluorophores with strong fluorogenicity have been difficult to realize. Here, we report close proximity tetrazine–dye conjugates with minimal distance between tetrazine and the fluorophore. Two synthetic routes give access to a series of cell-permeable and -impermeable dyes including highly fluorogen…
CCDC 1897052: Experimental Crystal Structure Determination
Related Article: Ephraim Prantl, Bernd Kohl, Dimitrij Ryvlin, Philipp Biegger, Hubert Wadepohl, Frank Rominger, Uwe H. F. Bunz, Michael Mastalerz, Siegfried R. Waldvogel|2019|ChemPlusChem|84|1239|doi:10.1002/cplu.201900189
CCDC 1897051: Experimental Crystal Structure Determination
Related Article: Ephraim Prantl, Bernd Kohl, Dimitrij Ryvlin, Philipp Biegger, Hubert Wadepohl, Frank Rominger, Uwe H. F. Bunz, Michael Mastalerz, Siegfried R. Waldvogel|2019|ChemPlusChem|84|1239|doi:10.1002/cplu.201900189