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

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

Abstract

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 efficient 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 first 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 affinity of the PDI core, affecting electrochemical and spectroelectochemcial behavior of the dyad without significantly affecting the solid-state packing of the molecules.

Citation

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. https://doi.org/10.1021/acsomega.8b02457

• 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
• DOI: https://doi.org/10.1021/acsomega.8b02457
• Public URL: https://nottingham-repository.worktribe.com/output/1436090
• Publisher URL: https://pubs.acs.org/doi/10.1021/acsomega.8b02457
• Contract Date: Dec 21, 2018