Donor-Acceptor Iptycenes with Thermally Activated Delayed Fluorescence

Author(s)
Voll, Constantin-Chri Alexander; Engelhart, Jens; Einzinger, Markus; Baldo, Marc A; Swager, Timothy M
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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
Date issued
2017-07
URI
http://hdl.handle.net/1721.1/114245
Department
Massachusetts Institute of Technology. Department of Chemistry; Massachusetts Institute of Technology. Department of Electrical Engineering and Computer Science
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
ISSN
1434-193X
1099-0690
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