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Thionated perylene diimide–phenothiazine dyad: synthesis, structure, and electrochemical studies

Pearce, Nicholas; Davies, E. Stephen; Lewis, William; Champness, Neil R.


Nicholas Pearce

William Lewis

Neil R. Champness


Perylene diimides (PDIs) are promising candidates for n-type semiconductor materials and, thus, for use in organic electronics. Thionation of the imide moiety provides an e?cient strategy to control the donor?acceptor gap of these types of compounds, although the degree and selectivity of thionation can be hard to achieve. Through the design of a sterically encumbered PDI?phenothiazine dyad, a previously unattained geminal thionation pattern has been realized, providing the ?rst example of a perylene-monoimide-monothioimide. The electrochemical and solid-state structural properties of this uniquely thionated dyad are reported and compared to those of the nonthionated parent molecule. It is found that thionation enhances the electron a?nity of the PDI core, a?ecting electrochemical and spectroelectochemcial behavior of the dyad without signi?cantly a?ecting the solid-state packing of the molecules.


Pearce, N., Davies, E. S., Lewis, W., & Champness, N. R. (2018). Thionated perylene diimide–phenothiazine dyad: synthesis, structure, and electrochemical studies. ACS Omega, 3(10), 14236-14244.

Journal Article Type Article
Acceptance Date Oct 16, 2018
Online Publication Date Oct 26, 2018
Publication Date Oct 31, 2018
Deposit Date Dec 21, 2018
Publicly Available Date Dec 21, 2018
Journal ACS Omega
Electronic ISSN 2470-1343
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 3
Issue 10
Pages 14236-14244
Public URL
Publisher URL


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