Síntese de derivados da vanilina e aplicação do composto (E)-4-(4-hidroxi-3-metoxifenil)but-3-en-2-ona em dispositivo orgânico fotossensível

Abstract

Vanillin is the main component responsible for the aroma of vanilla, but it is also a versatile reagent for organic synthesis. In this work, vanillin was extracted from vanilla sugar as an alternative to obtaining vanillin and the sample was characterized by measuring its melting point. Three compounds derived from vanillin were synthesized (using vanillin from a commercial source): (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (2) and (1E, 4E)-1-(4-hydroxy-3-methoxyphenyl)-5-phenylpenta-1,4-dien-3-one (5) were synthesized via aldol condensation reactions, and compound (E)-2-methoxy-4-(3-oxobut-1-en-1-yl)phenyl acetate (4) via an acetylation reaction of compound 2. Compounds 2 and 4 were synthesized with yields of 80% and 71%, respectively. It was not possible to determine the yield of compound 5. All the compounds synthesized were characterized using melting point measurement and mass spectrometry. Compound 2 was further characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. Compound 2 was tested as a photosensitizing material in a Dye Sensitized Solar Cell (DSSC), with electrochemical parameters of a potential of 0.5 V and a current of 0.3 mA cm-2. These results are promising, since this is a low-cost compound that can be used as a standard for the synthesis of other molecules with potential applicability, with the aim of improving its properties as a colorant.