Synthesis of an alkylthio-substituted dibenz[a,j]anthracene with improved solubility via the oxidative photocyclization of 1,3-distyrylbenzene derivatives

A series of 1,3-distyrylbenzene compounds bearing different substituents at the 2-position have been synthesized and subjected to an oxidative photocyclization process. The 1,3-distyrylbenzene compounds substituted with chloro, alkylthio, and diphenylphosphino groups at the 2-position afforded dibenz[a,j]anthracene derivatives, whereas those bearing methyl, trimethylsilyl, dimethylamino, butoxy, and fluoro groups gave benzo[c]chrysene derivatives. The solubility of dibenz[a,j]anthracene in organic solvents was improved by the introduction of alkylthio groups.