Synthesis, Characterization, and Properties of BN-Fluoranthenes

Synthesis, Characterization, and Properties of BN-Fluoranthenes

Boron/nitrogen-doped fluoranthenes, a new class of BN-doped cyclopenta-fused polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type nitrogen directed C–H borylation. Regioselective bromination of BN-fluoranthene (3a) gave mono- and dibrominated BN-fluoranthenes. The halogenated BN-fluo...

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Veröffentlicht in:Organic letters 2022-08, Vol.24 (30), p.5503-5508
Hauptverfasser: Li, Erlong, Jin, Mengjia, Jiang, Ruijun, Zhang, Lei, Zhang, Yanli, Liu, Meiyan, Wu, Xiaoming, Liu, Xuguang
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container_end_page 5508
container_issue 30
container_start_page 5503
container_title Organic letters
container_volume 24
creator Li, Erlong
Jin, Mengjia
Jiang, Ruijun
Zhang, Lei
Zhang, Yanli
Liu, Meiyan
Wu, Xiaoming
Liu, Xuguang
description Boron/nitrogen-doped fluoranthenes, a new class of BN-doped cyclopenta-fused polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type nitrogen directed C–H borylation. Regioselective bromination of BN-fluoranthene (3a) gave mono- and dibrominated BN-fluoranthenes. The halogenated BN-fluoranthene (3b) can undergo various of further cross-coupling reactions to deliver a series of BN-fluoranthenes. Moreover, incorporating BN unit in to fluoranthene resulted in a wider HOMO–LUMO energy gaps. The aromaticities of the BN-fluoranthene (3a) were quantified by experimental and computational studies.
doi_str_mv 10.1021/acs.orglett.2c01342
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