828916-46-7Relevant academic research and scientific papers
Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant
Stress, Cedric J.,Schmidt, Pascal J.,Gillingham, Dennis. G.
supporting information, p. 5529 - 5533 (2016/07/06)
We use kinetic data, photophysical properties, and mechanistic analyses to compare recently developed high-rate constant oxime and hydrazone formations. We show that when Schiff base formation between aldehydes and arylhydrazines is carried out with an appropriately positioned boron atom, then aromatic B-N heterocycles form irreversibly. These consist of an extended aromatic structure amenable to the tailoring of specific properties such as reaction rate and fluorescence. The reactions work best in neutral aqueous buffer and can be designed to be fluorogenic-properties which are particularly interesting in bioconjugation.
Fluorescence sensing based on cation-induced conformational switching: Copper-selective modulation of the photoinduced intramolecular charge transfer of a donor-acceptor biphenyl fluorophore
Cody, John,Fahrni, Christoph J.
, p. 11099 - 11107 (2007/10/03)
The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4′-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by 1H NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers that are locked into a more flattened geometry upon coordination of Cu(I).
