Incorporating electron withdrawing groups (e.g. -F, -Cl, -CN, -CF3, -COOR, -NO2) onto aromatics leads to increased electron affinities (EAs) of the corresponding compound and provides a potential pathway to solve the air-stability problem faced by current n-type organic semiconductor materials. Perfluoroalkyls (-CnF2n+1), a group of unique fluorous electron withdrawing substituents, provides the possibility of both increased EAs and better solid state packing, both of which are key to improving current n-type organic semiconductor performance. Here we report the synthesis, characterization, and crystal structures of perfluoroalkylated benzo[a,c]phenazine derivatives. We find that asymmetric perfluoroalkylation of the benzophenazine ring assists to increase the intermolecular interaction energy and leads to better solid state structure due to reduced steric interactions through antiparallel lamellar stacking and electronic effects induced by asymmetric perfluoroalkylation increasing intermolecular cohesion.

Perfluoroalkylated benzophenazines: Synthesis, characterization, and potential applications as n-type organic semiconductor materials

248th National Meeting (2014)

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