The small molecular polycyclic aromatic hydrocarbons (commonly known by acenes) are the potential alternatives of traditional silicon-based semiconducting materials for the opto-electronic applications. Although higher acenes exhibit desired semiconducting properties, these molecules are not very stable under ambient conditions. In order to improve their stability and processibilty, we propose to incorporate a redox-active metal center on acene backbone <i>via</i> cyclopentadienyl moiety. To achieve the goal, we are working on developing viable synthetic methodologies to synthesize ferrocene-capped acene complexes. The project involves the Friedel-Crafts acylation of ferrocene with 1,2-dicarboxylic anhydrides to give keto carboxylic acids. The carbonyl group is reduced to methylene in order to activate the cyclopentadienyl rings towards ring-closure using zinc powder activated by copper. The ring-closing in the presence of trifluoroacetic anhydride followed by oxidation results in formation of ferrocene-capped quinones. These quinones will be subjected to reductive aromatization by incorporating electron-withdrawing cyano (CN) groups at <i>peri </i>positions of ferrocenyl moiety. Synthesis and characterization including molecular structures of different metallocenes will be discussed.

Synthetic methodologies for ferrocene-fused acenes

255th National Meeting (2018)

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