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Donor-Acceptor Iptycenes with Thermally Activated Delayed Fluorescence

dc.contributor.authorVoll, Constantin-Chri Alexander
dc.contributor.authorEngelhart, Jens
dc.contributor.authorEinzinger, Markus
dc.contributor.authorBaldo, Marc A
dc.contributor.authorSwager, Timothy M
dc.date.accessioned2018-03-21T15:05:47Z
dc.date.available2018-03-21T15:05:47Z
dc.date.issued2017-07
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.urihttp://hdl.handle.net/1721.1/114245
dc.description.abstractA 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-couplingen_US
dc.language.isoen_US
dc.publisherWiley Blackwellen_US
dc.relation.isversionofhttp://dx.doi.org/10.1002/ejoc.201700703en_US
dc.rightsCreative Commons Attribution-Noncommercial-Share Alikeen_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/en_US
dc.sourceProf. Swager via Erja Kajosaloen_US
dc.titleDonor-Acceptor Iptycenes with Thermally Activated Delayed Fluorescenceen_US
dc.typeArticleen_US
dc.identifier.citationVoll, 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, Weinheimen_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Electrical Engineering and Computer Scienceen_US
dc.contributor.approverSwager, Timothy Men_US
dc.contributor.mitauthorVoll, Constantin-Chri Alexander
dc.contributor.mitauthorEngelhart, Jens
dc.contributor.mitauthorEinzinger, Markus
dc.contributor.mitauthorBaldo, Marc A
dc.contributor.mitauthorSwager, Timothy M
dc.relation.journalEuropean Journal of Organic Chemistryen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsVoll, Constantin-Christian A.; Engelhart, Jens U.; Einzinger, Markus; Baldo, Marc A.; Swager, Timothy M.en_US
dspace.embargo.termsNen_US
dc.identifier.orcidhttps://orcid.org/0000-0003-2769-3321
dc.identifier.orcidhttps://orcid.org/0000-0001-9711-7368
dc.identifier.orcidhttps://orcid.org/0000-0002-4952-2905
dc.identifier.orcidhttps://orcid.org/0000-0003-2201-5257
mit.licenseOPEN_ACCESS_POLICYen_US


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