Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines

• Main Authors: Tebogo Ankie Khoza, Marole Maria Maluleka, Neliswa Mama, Malose Jack Mphahlele
• Format: Article
• Language: English
• Published: MDPI AG 2012-11-01
• Series: Molecules
• Subjects: 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones; 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones; 2-aryl-6,8-dibromoquinolin-4(1H)-ones; 2-aryl-6,8-dibromo-4-methoxyquinolines; Suzuki-Miyaura cross-coupling; 2-aryl-6,8-bis(2-aryl-ethenyl)-4-methoxyquinolines; photophysical properties
• Online Access: http://www.mdpi.com/1420-3049/17/12/14186

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-methoxy-quinolines 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.