Donor-Acceptor Iptycenes with Thermally Activated Delayed Fluorescence
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ejoc.201700703_R1(1).pdf
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Author(s)
Voll, Constantin-Chri Alexander
Engelhart, Jens
Einzinger, Markus
Baldo, Marc A
Swager, Timothy M
Date Issued
July 2017
Journal
European Journal of Organic Chemistry
Publisher
Wiley Blackwell
Citation
Voll, Constantin-Christian A. et al. “Donor-Acceptor Iptycenes with Thermally Activated Delayed Fluorescence.” European Journal of Organic Chemistry 2017, 32 (August 2017): 4846–4851 © 2017 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Version
Author's final manuscript
Abstract
A new donor–acceptor iptycene containing carbazole donors and a thiadiazoloquinoxaline acceptor was synthesized and its photo‐ and electrochemical properties evaluated. The key intermediate 1 allows a lateral modification through cross‐coupling, and the (triisopropylsilyl)acetylene product 2 exhibits bright yellow fluorescence with emission lifetimes of 2.42 µs in deoxygenated hexane. The long lifetime and high quantum efficiency (73 %) is quenched by O₂ and therefore attributed to thermally activated delayed fluorescence (TADF). This approach allows functionalization through cross‐coupling reactions and depicts a promising scaffold for the synthesis of TADF‐active molecules.Keywords: Functional organic materials; Fluorescence; Donor–acceptor systems; Iptycenes; Cross-coupling
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Department of Electrical Engineering and Computer Science
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1002/ejoc.201700703
