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

Julius A. Knöller; Guoyun Meng; Xiang Wang; David Hall; Anton Pershin; David Beljonne; Yoann Olivier; Sabine Laschat; Eli Zysman-Colman; Suning Wang

doi:10.1002/anie.201912340

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

Julius A. Knöller, Guoyun Meng, Xiang Wang, David Hall, Anton Pershin, David Beljonne, Yoann Olivier, Sabine Laschat, Eli Zysman-Colman, Suning Wang

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

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Résumé

New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3–6 a/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 2 a/2 b via intramolecular borylation and sequential B−Mes bond cleavage in the presence of BBr₃. Subsequent reaction of 2 a/2 b 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 ΔE_ST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).

langue originale	Anglais
Pages (de - à)	3156-3160
Nombre de pages	5
journal	Angewandte Chemie - International Edition
Volume	59
Numéro de publication	8
Les DOIs	https://doi.org/10.1002/anie.201912340
Etat de la publication	Publié - 17 févr. 2020

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10.1002/anie.201912340

2020_OlivierY_articleAccepted author manuscript, 520 KB

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CCDC 1946490: Experimental Crystal Structure Determination
Knöller, J. A. (Créateur), Meng, G. (Créateur), Wang, X. (Créateur), Hall, D. (Créateur), Pershin, A. (Créateur), Beljonne, D. (Créateur), Olivier, Y. (Contributeur), Laschat, S. (Créateur), Zysman‐Colman, E. (Créateur) & Wang, S. (Créateur), University of Namur, 17 févr. 2020
DOI: 10.5517/ccdc.csd.cc23bh0z, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23bh0z&sid=DataCite
Ensemble de données
CCDC 1946485: Experimental Crystal Structure Determination
Knöller, J. A. (Créateur), Meng, G. (Créateur), Wang, X. (Créateur), Hall, D. (Créateur), Pershin, A. (Créateur), Beljonne, D. (Créateur), Olivier, Y. (Contributeur), Laschat, S. (Créateur), Zysman‐Colman, E. (Créateur) & Wang, S. (Créateur), University of Namur, 17 févr. 2020
DOI: 10.5517/ccdc.csd.cc23bgvs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23bgvs&sid=DataCite
Ensemble de données
CCDC 1946488: Experimental Crystal Structure Determination
Knöller, J. A. (Créateur), Meng, G. (Créateur), Wang, X. (Créateur), Hall, D. (Créateur), Pershin, A. (Créateur), Beljonne, D. (Créateur), Olivier, Y. (Contributeur), Laschat, S. (Créateur), Zysman‐Colman, E. (Créateur) & Wang, S. (Créateur), University of Namur, 17 févr. 2020
DOI: 10.5517/ccdc.csd.cc23bgyw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23bgyw&sid=DataCite
Ensemble de données

Contient cette citation

@article{ee13ecbb6a5e4d369f2a31ce54be7877,

title = "Intramolecular Borylation via Sequential B−Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes",

abstract = "New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3–6 a/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 2 a/2 b via intramolecular borylation and sequential B−Mes bond cleavage in the presence of BBr3. Subsequent reaction of 2 a/2 b 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 ΔEST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).",

keywords = "B,N,B-benzo[4]helicenes, boron, divergent synthesis, luminescence, synthetic methods",

author = "Kn{\"o}ller, {Julius A.} and Guoyun Meng and Xiang Wang and David Hall and Anton Pershin and David Beljonne and Yoann Olivier and Sabine Laschat and Eli Zysman-Colman and Suning Wang",

note = "Funding Information: We thank the Natural Sciences and Engineering Research Council of Canada and the Leverhulme Trust (RPG-2016-47) for financial support. J. A. Kn{\"o}ller thanks the Baden W{\"u}rttemberg Stiftung for a scholarship as well as Queen′s and Stuttgart University for enabling this research through the Dual Degree Masters program. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = feb,

day = "17",

doi = "10.1002/anie.201912340",

language = "English",

volume = "59",

pages = "3156--3160",

journal = "Angewandte Chemie - International Edition",

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Intramolecular Borylation via Sequential B−Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes. / Knöller, Julius A.; Meng, Guoyun; Wang, Xiang et al.
Dans: Angewandte Chemie - International Edition, Vol 59, Numéro 8, 17.02.2020, p. 3156-3160.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - Intramolecular Borylation via Sequential B−Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes

AU - Knöller, Julius A.

AU - Meng, Guoyun

AU - Wang, Xiang

AU - Hall, David

AU - Pershin, Anton

AU - Beljonne, David

AU - Olivier, Yoann

AU - Laschat, Sabine

AU - Zysman-Colman, Eli

AU - Wang, Suning

N1 - Funding Information: We 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. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/2/17

Y1 - 2020/2/17

N2 - New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3–6 a/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 2 a/2 b via intramolecular borylation and sequential B−Mes bond cleavage in the presence of BBr3. Subsequent reaction of 2 a/2 b 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 ΔEST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).

AB - New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3–6 a/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 2 a/2 b via intramolecular borylation and sequential B−Mes bond cleavage in the presence of BBr3. Subsequent reaction of 2 a/2 b 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 ΔEST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).

KW - B,N,B-benzo[4]helicenes

KW - boron

KW - divergent synthesis

KW - luminescence

KW - synthetic methods

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U2 - 10.1002/anie.201912340

DO - 10.1002/anie.201912340

M3 - Article

C2 - 31670891

AN - SCOPUS:85078605507

SN - 1433-7851

VL - 59

SP - 3156

EP - 3160

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 8

ER -

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

Résumé

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Autres fichiers et liens

Empreinte digitale

Équipement

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Ensembles de données

CCDC 1946490: Experimental Crystal Structure Determination

CCDC 1946485: Experimental Crystal Structure Determination

CCDC 1946488: Experimental Crystal Structure Determination

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