Thionated Perylene Diimide?Phenothiazine Dyad: Synthesis,Structure, and Electrochemical Studies

摘要

Perylene diimides (PDIs) are promising candidates for n-type semiconductor materials and, thus, for use inorganic electronics. Thionation of the imide moiety provides an efficient strategy to control the donor?acceptor gap of thesetypes of compounds, although the degree and selectivity of thionation can be hard to achieve. Through the design of a stericallyencumbered PDI?phenothiazine dyad, a previously unattained geminal thionation pattern has been realized, providing the firstexample of a perylene-monoimide-monothioimide. The electrochemical and solid-state structural properties of this uniquelythionated dyad are reported and compared to those of the nonthionated parent molecule. It is found that thionation enhancesthe electron affinity of the PDI core, affecting electrochemical and spectroelectochemcial behavior of the dyad withoutsignificantly affecting the solid-state packing of the molecules.