Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 1, Pages 108-117Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02283
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- British Columbia Knowledge Development Fund (BCKDF)
- NSERC
- Canada Research Chairs program
- University of British Columbia (UBC)
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An N-phenylbenzimidazole constrained in a coplanar fashion with a methylene tether (IMAC) was designed and used to prepare a series of emitters exhibiting thermally activated delayed fluorescence (TADF). Four novel TADF emitters using 9,9-dimethylacridine, phenoxazine, phenothiazine, and bis(di-ptolylamino)carbazole as the donor group were designed and synthesized using IMAC as the acceptor. Additionally, two deepblue fluorescent emitters were prepared with carbazole and tercarbazole as the donor moieties. The twisted conformation between donor and acceptor in these molecules resulted in effective spatial separation of the HOMO and LUMO and small singlet-triplet energy gaps. Crystallographic properties, electronic structures, thermal stabilities, photophysical properties, and energy levels were studied systematically. Ultimately, these findings provide a promising opportunity for the design and synthesis of highly efficient TADF materials based on IMAC derivatives.
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