Revealing Resonance Effects and Intramolecular Dipole Interactions in the Positional Isomers of Benzonitrile-Core Thermally Activated Delayed Fluorescence Materials

Kukhta, N.A.; Higginbotham, H.F.; Matulaitis, T.; Danos, A.; Bismillah, A.N.; Haase, N.; Etherington, M.K.; Yufit, D.S.; McGonigal, P.R.; Gražulevičius, J.V.; Monkman, A.P.

Abstract

We report on the properties of the three positional isomers of (2,7-di-tert-butyl-9,9-dimethylacridin-10(9H)-yl)benzonitrile, which are found to have comparable donor steric environments and donor–acceptor dihedral angles. An unexpected intramolecular dipole interaction imparts a unique molecular geometry to the ortho-linked isomer, while comparison of the meta- and para-isomers uncovers how positional differences in acceptor strengths (a consequence of differences in aromatic π-system electron density) lead to very different triplet harvesting and emission properties. These positional-isomer effects on TADF follow the well-known aromatic directing rules from organic synthesis, in keeping with their common origin arising from contributions of multiple electronic resonance structures. Understanding these positional effects and methods of dihedral control is critical to the future design of efficient TADF emitters.

Citation

Kukhta, N., Higginbotham, H., Matulaitis, T., Danos, A., Bismillah, A., Haase, N., …Monkman, A. (2019). Revealing Resonance Effects and Intramolecular Dipole Interactions in the Positional Isomers of Benzonitrile-Core Thermally Activated Delayed Fluorescence Materials. Journal of Materials Chemistry C Materials for optical and electronic devices, 7(30), 9184-9194. https://doi.org/10.1039/c9tc02742d

• Journal Article Type: Article
• Acceptance Date: Jun 28, 2019
• Online Publication Date: Jul 12, 2019
• Publication Date: Aug 14, 2019
• Deposit Date: Jun 28, 2019
• Publicly Available Date: Aug 2, 2019
• Journal: Journal of Materials Chemistry C Materials for optical and electronic devices
• Print ISSN: 2050-7526
• Electronic ISSN: 2050-7534
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 7
• Issue: 30
• Pages: 9184-9194
• DOI: https://doi.org/10.1039/c9tc02742d
• Public URL: https://durham-repository.worktribe.com/output/1298058