Synthesis of a Blue-Emissive Azaborathia[9]helicene by Silicon-Boron Exchange from Unusual Atropisomeric Teraryls.
Atropisomerism
Azaboroles
Borylation
Chirality
Helicenes
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
24 Jul 2023
24 Jul 2023
Historique:
received:
24
03
2023
medline:
14
5
2023
pubmed:
14
5
2023
entrez:
13
5
2023
Statut:
ppublish
Résumé
We report the concise synthesis and chir(optical) properties of an azaborathia[9]helicene consisting of two thienoazaborole motifs. The key intermediate, a highly congested teraryl with nearly parallel isoquinoline moieties, was generated as a mixture of atropisomers upon fusion of the central thiophene ring of the dithienothiophene moiety. These diastereomers were characterized by single crystal X-ray analysis revealing intriguing interactions in the solid state. Subsequent insertion of boron into the aromatic scaffold via silicon-boron exchange involving triisopropylsilyl groups fixed the helical geometry, thereby establishing a novel method for the preparation of azaboroles. The ligand exchange at boron in the final step afforded the blue emitter displaying a fluorescence quantum yield of 0.17 in CH
Identifiants
pubmed: 37178395
doi: 10.1002/anie.202304291
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202304291Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : NO 1459/1-1
Organisme : Deutsche Forschungsgemeinschaft
ID : 444286426
Organisme : Hector Fellow Academy
ID : 200003521
Organisme : Hector Fellow Academy
ID : 250000121
Organisme : Hector Fellow Academy
ID : 700000121
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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Deposition Numbers 2247122 (for BA-TMS), 2247233 (for BA-TIPS), 2247235 (for OA-TMS2), 2247236 (for OA-TIPS2), 2247242 (for rac-TA-TIPS2), 2247243 (for (Ra,Sa)-TA-TIPS2), 2247247 (for TA), and 2247249 (for rac-H1-Me4) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
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