Síntese de derivados de fluoresceína contendo Selênio: ácido arilselenínico como agente selenilante

Abstract

This dissertation describes an efficient methodology for the synthesis of 3',6'-dihydroxy-4'-(phenylselanyl)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one and 3',6'-dihydroxy-4',5'-bis(phenylselanyl)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one, using arylseleninic acids as selenylating agents and ethanol as a solvent. These acids are stable on the bench and easy to handle, producing only water and diselenide as by-products, which can be reused. Furthermore, using ethanol as a solvent makes the reaction more sustainable due to its renewable and green origin. As a result, twelve examples were synthesized, nine unprecedenteding in the literature. It was possible to prepare derivatives from electron-rich and electron-poor arylseleninic acids in moderate to good yields. The photophysical properties of 3',6'-dihydroxy-4'-(phenylselanyl)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one and 3',6'-dihydroxy-4',5'-bis(phenylselanyl)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one were studied in polar solvents and compared with data for 3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one.