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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.

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


Authors

N.A. Kukhta

H.F. Higginbotham

T. Matulaitis

A.N. Bismillah

N. Haase

M.K. Etherington

J.V. Gražulevičius



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 Mar 29, 2024
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

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