Journal Article

PUBDB-2026-01245

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Fraternal twins: B$_2$O$_2$- or B$_2$N$_2$-doped polycyclic π systems and their formation mechanism via regiodivergent Au- versus amine-catalyzed cyclizations

Mittag, S.Extern* ; Klopf, J. ; Virovets, A.Extern* ; Peresypkina, E.Extern* ; Lerner, H.-W. ; Helten, H. (Corresponding author) ; Wagner, M. (Corresponding author)Extern*

2026
Soc. London

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Please use a persistent id in citations: doi:10.1039/D6DT00412A  doi:10.3204/PUBDB-2026-01245

Abstract: BE-doped polycyclic aromatic hydrocarbons (PAHs; E = NR, O) often exhibit superior optoelectronic properties compared to their carbonaceous congeners. Herein, we report an efficient and convenient synthetic route to this compound class, based on the intramolecular addition of aryl(Mes)BE–H bonds to ortho-positioned butadiyne substituents. The reactions can proceed either under Au(I) or NEt3 catalysis, with the same substrate giving rise to distinct addition patterns. Treatment of o-MesB(OH)-diphenylbutadiyne or o,o’-bis[MesB(OH)]-diphenylbutadiyne with [Au(PPh3)(NTf2)] furnishes an ethynyl-substituted BO-naphthalene or a (BO)2-binaphthyl (B2O2; via 2,3-OC-addition), respectively. In contrast, NEt3-catalyzed double cyclization of o,o’-bis[MesB(OH)]-diphenylbutadiyne affords the corresponding (BO)2 naphthylbenzofulvene (iso-B2O2; via 1,3-OC-addition). Replacement of NEt3 with ethylenediamine generates the analogous (BN)2-doped PAH (iso-B2N2). Notably, both B2O2 and iso-B2N2 show high photoluminescence quantum yields of ΦPL = 80% and 93%, respectively. Using the formation of iso-B2O2 as a model reaction, a plausible mechanistic scenario was elucidated through quantum-chemical calculations and systematic probe experiments, providing further novel BE-doped PAHs.

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Contributing Institute(s):

1. FS DOOR-User (FS DOOR-User)

Research Program(s):

1. 6G3 - PETRA III (DESY) (POF4-6G3) (POF4-6G3)
2. FS-Proposal: I-20231039 (I-20231039) (I-20231039)
3. FS-Proposal: R-20240674 (R-20240674) (R-20240674)
4. FS-Proposal: R-20250872 (R-20250872) (R-20250872)

Experiment(s):

1. PETRA Beamline P24 (PETRA III)

Appears in the scientific report 2026

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Database coverage:
; ; ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; Ebsco Academic Search ; Essential Science Indicators ; IF < 5 ; JCR ; National-Konsortium ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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