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Molecules 2012, 17(12), 14186-14204; doi:10.3390/molecules171214186
Article

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

1, 1, 2 and 1,*
1 Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa 2 Department of Chemistry, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South Africa
* Author to whom correspondence should be addressed.
Received: 8 November 2012 / Revised: 20 November 2012 / Accepted: 23 November 2012 / Published: 30 November 2012
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: 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 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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Khoza, T.A.; Maluleka, M.M.; Mama, N.; Mphahlele, M.J. Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines. Molecules 2012, 17, 14186-14204.

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