Synthesis and photophysical properties of 2-Aryl-6,8-bis(arylethenyl)-4- methoxyquinolines

Abstract

Iodine-methanol mediated oxidative-Aromatization of 2-Aryl-6,8-dibromo-2,3- dihydroquinolin-4(1H)-ones afforded the corresponding 2-Aryl-6,8-dibromo-4- methoxyquinolines in high yield and purity. The isomeric 1-(2-Amino-3,5- dibromophenyl)-3-Aryl-2- propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-Aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-Aryl-6,8- dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4- methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-Aryl-6,8-bis(2-Arylethenyl)- 4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined. © 2012 by the authors.