Synthesis of Phenanthroline-Based Polyphenylenes via a Diels-Alder Cycloaddition Reaction

Abstract

Abstract Conjugated polyarenes have been the focus of considerable interest due to their potential for serving as materials for electroluminescence devices, since they possess high fluorescence efficiency and are technically processable. A novel Family of phenanthroline-based compounds were synthesised via a [2+4] Diels-Alder cycloaddition reaction between specifically designed cyclopentadienone based synthons that incorporate the already fused phenanthroline moiety 11b-Hydroxy-1,3- diphenyl-1,11b-dihydro-7,8-diaza-cyclophenta[l]phenanthrene-2-one (1a) and 11b- Hy d r o x y - 1 , 3 - d i ( 4 - t e r t - b u t y l p h e n y l ) - 1 , 1 1 b - d i h y d r o - 7 , 8 - d i a z a - cyclophenta[l]phenanthrene-2-one (1b) and various di-substituted acetylenes. These systems have been found to display tuneable fluorescent capabilities, which make them promising material for application in optoelectronics as well showing excellent metal coordination potential