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Intramolecular borylation via sequential B-Mes bond cleavage for the divergent synthesis of B,N,B-doped benzo[4]helicenes
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dc.contributor.author | Knöller, Julius | |
dc.contributor.author | Meng, Guoyun | |
dc.contributor.author | Wang, Xiang | |
dc.contributor.author | Hall, David | |
dc.contributor.author | Pershin, Anton | |
dc.contributor.author | Beljonne, David | |
dc.contributor.author | Olivier, Yoann | |
dc.contributor.author | Laschat, Sabine | |
dc.contributor.author | Zysman-Colman, Eli | |
dc.contributor.author | Wang, Suning | |
dc.date.accessioned | 2021-01-16T00:35:48Z | |
dc.date.available | 2021-01-16T00:35:48Z | |
dc.date.issued | 2020-01-16 | |
dc.identifier | 262929747 | |
dc.identifier | 9c813484-9c25-4628-bc66-948061f48010 | |
dc.identifier | 85078605507 | |
dc.identifier | 000507414700001 | |
dc.identifier.citation | Knöller , J , Meng , G , Wang , X , Hall , D , Pershin , A , Beljonne , D , Olivier , Y , Laschat , S , Zysman-Colman , E & Wang , S 2020 , ' Intramolecular borylation via sequential B-Mes bond cleavage for the divergent synthesis of B,N,B-doped benzo[4]helicenes ' , Angewandte Chemie International Edition , vol. Early View . https://doi.org/10.1002/anie.201912340 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | ORCID: /0000-0001-7183-6022/work/67919681 | |
dc.identifier.uri | https://hdl.handle.net/10023/21276 | |
dc.description | Authors thank the Natural Sciences and Engineering Research Council of Canada and the Leverhulme Trust (RPG-2016-47) for financial support. J. A. Knöller thanks the Baden Württemberg Stiftung for a scholarship as well as Queen's and Stuttgart University for enabling this research through the Dual Degree Masters program. | en |
dc.description.abstract | New 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 BBr3. 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 ∆EST suggest the potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs). | |
dc.format.extent | 2517309 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Synthetic methods | en |
dc.subject | Boron | en |
dc.subject | Luminescence | en |
dc.subject | B,N,B- benzo[4]helicenes | en |
dc.subject | Divergent synthesis | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Intramolecular borylation via sequential B-Mes bond cleavage for the divergent synthesis of B,N,B-doped benzo[4]helicenes | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Organic Semiconductor Centre | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/anie.201912340 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2021-01-16 | |
dc.identifier.grantnumber | RPG-2016-047 | en |
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