Synthesis, evaluation of luminescent properties, and applications of organochalcogen-functionalized fluorophores.
Aiming to synthesize Selenium and tellurium fluorescent organic compounds capable of acting as “on/off” devices by photoinduced electron transfer (PET) and which also have biological activity, the following starting materials were prepared: diphenyl dichalcogenides, 4- (phenylchalcogenyl) -benzaldehydes, 4- (phenylchalcogenyl) -benzylamines, with an attempt to produce 3- (phenylchalcogenyl) –propylamines. These derivatives constitute a collection with six compounds that were characterized by 1H, 13C NMR, and high-resolution mass spectrometry. With this, different protocols were explored in an attempt to conjugate these compounds to the fluorophores 4-amino-7-methyl-coumarin, 1-aminomethyl-pyrene, 5-fluorescein isothiocyanate, and rhodamine B isothiocyanate. Among these, only the conjugation of 1 -aminomethyl-pyrene was successful for both chalcogens. The same characterization approach was also applied to a series of benzazoles comprised of benzimidazoles and benzothiazoles which had their partial photophysical characterization carried out together with the 1-aminomethyl-pyrene compounds. The absorption, emission, and excitation spectra were obtained for the nine compounds, and it was not possible to get quantum yields and lifetime due to limitations present in the equipment available. Finally, using dimethylsulfoxide (DMSO) and / or water as solvents, tests for adding dithiothreitol (DTT), hydrogen peroxide, L-Cysteine, hydrochloric acid and sodium hydroxide solutions were performed in order to observe the behavior of the emission intensity during oxidation and reduction of the aforementioned compounds.