Microwave-assisted synthesis of a new fluorinated Biphenyl-Schiff base with potential application in nonlinear optical / Síntese assistida por micro-ondas de uma nova Bifenil-Base de Schiff Fluorada com potencial aplicação em óptica não linear

The new fluorinated Biphenyl-Schiff Base 3 was synthesized by a synthetic route involving three steps, with the formation of two intermediates precursors. Primarily by the result of a Suzuki-Miyaura cross-coupling reaction forming the fluorinated 4-aminobiphenyl ( 1 ) and later by the result of the nucleophilic substitution S N 2 obtaining the intermediate 4-[2-(dimethylamino)ethoxy]-benzaldehyde ( 2 ). The Schiff base 3 was obtained through the condensation reaction between intermediates 1 and 2 . The methodology involving the reaction to form intermediate 2 proved to be more effective when aided by microwave irradiation providing a significantly higher yield in a shorter time. The GC-MS showed that all compounds were synthesized by the proximity of the calculated m/z ratio and that found. In addition, theoretical calculations showed that the new fluorinated Biphenyl-Schiff Base 3 obtained a value for the first hyperpolarizability ( of 45.1 x 10 -30 esu that is approximately five times greater than the experimental value of 9.2 x 10 -30 esu for the reference compound (p-nitroaniline).