Síntese de derivados da dibenzalacetona n-substituídas e estudo do efeito solvatocrômico

Abstract

The organic synthesis was born in 1828 through the synthesis of urea by Friederich Wohler, the synthesis of dibenzalacetones are molecules that have been increasing in the scientific community and this is due to its wide range of applications, which is possible due to its conjugated system, this feature allows applications in biological activities such as anti-inflammatory and antioxidant as well as applications in photoprotectors and the study of the solvatochromic effect. The present work aims at the synthesis of dibenzalacetone derivatives and the study of the solvatochromic effect. In this sense, 13 derivatives of n-substituted dibenzalacetones were obtained from an aldol condensation reaction, with some modifications in the synthetic routes in time intervals ranging from 15 min. - 72 h, with yields in the range 43 - 96%. These compounds were characterized by spectroscopic techniques of Hydrogen Nuclear Magnetic Resonance (1H NMR), Carbon 13 (1³C NMR - DEPTQ) and Fourier Transform Infrared (FTIR). In the analysis also solubility tests were performed, showing good solubility in DMSO and Chloroform and also the solvatochromic effect analysis was performed. In the UV-Vis tests with the use of polar solvents, changes for longer wavelengths were observed, and in the fluorescence emission spectrum analysis tests in solvents that present higher polarities, they also presented the highest intensities for most compounds. From the tests performed it is observed that some compounds present good prospects for applications in photoprotectors and biological activities, such as anti-inflammatory and cytotoxic activities.