title: 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-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.
authors.affiliation: Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa.
authors.forename: Tebogo Ankie
authors.initials: TA
authors.lastname: Khoza
authors.forename: Marole Maria
authors.initials: MM
authors.lastname: Maluleka
authors.forename: Neliswa
authors.initials: N
authors.lastname: Mama
authors.forename: Malose Jack
authors.initials: MJ
authors.lastname: Mphahlele
mesh_terms: D000042:Absorption; D005453:Fluorescence; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D011804:Quinolines; D007455:Iodine