Intramolecular Borylation via Sequential B‐Mes Bond Cleavage for the Divergent Synthesis of B,N,B‐doped Benzo[4]helicenes

dc.contributor.authorKnoeller, Juliusen
dc.contributor.authorMeng, Guoyunen
dc.contributor.authorWang, Xiangen
dc.contributor.authorHall, Daviden
dc.contributor.authorPershin, Antonen
dc.contributor.authorBeljonne, Daviden
dc.contributor.authorOlivier, Yoannen
dc.contributor.authorLaschat, Sabineen
dc.contributor.authorZysman-Colman, Elien
dc.contributor.authorWang, Suningen
dc.date.accessioned2020-01-03T19:46:04Z
dc.date.available2020-01-03T19:46:04Z
dc.date.issued2019
dc.description.abstractNew symmetric and unsymmetric B,N,B‐doped benzo[4]helicenes 3 ‐ 6a/b have been achieved in good yields, using a three‐step process, starting from N(tolyl) 3 in a highly divergent manner (7 examples). A borinic acid functionalized 1,4‐B,N‐anthracene 1 was found to display unprecedented reactivity, acting as a convenient and highly effective precursor for selective formation of bromo substituted B,N,B‐benzo[4]helicenes 2a / 2b via intramolecular borylation and sequential B‐Mes bond cleavage in presence of BBr 3 . Subsequent reaction of 2a / 2b with Ar‐Li provided a highly effective toolbox for the preparation of symmetrically/unsymmetrically functionalized B,N,B‐helicenes. Their high photoluminescence quantum yields along with the small Δ E ST suggest the potential as thermally activated delayed fluorescence (TADF) emitters for organic light‐emitting diodes (OLEDs).en
dc.identifier.doihttps://doi.org/10.1002/anie.201912340
dc.identifier.urihttp://hdl.handle.net/1974/27527
dc.language.isoenen
dc.rightsThis is the peer reviewed version of the following article: Intramolecular Borylation via Sequential B‐Mes Bond Cleavage for the Divergent Synthesis of B,N,B‐doped Benzo[4]helicenes, Angewandte chemie international edition, which has been published in final form at https://doi.org/10.1002/anie.201912340. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.en
dc.subjectSynthetic Methodsen
dc.subjectBoronen
dc.subjectLuminescenceen
dc.subjectHeterocyclesen
dc.subjectBorylationen
dc.titleIntramolecular Borylation via Sequential B‐Mes Bond Cleavage for the Divergent Synthesis of B,N,B‐doped Benzo[4]helicenesen
dc.typejournal articleen
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