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- W2736458539 abstract "Abstract Reaction of an N‐heterocyclic carbene (NHC)–borenium ion with 9,10‐distyrylanthracene forms four B−C bonds through two selective, tandem hydroboration–electrophilic C−H borylations to yield an isolable, crystallographically characterizable polycyclic diborenium ion as its [NTf 2 ] − salt ( 1 ). Dehydrogenation of 1 with TEMPO radical followed by acidic workup yields a 3,9‐diboraperylene as its corresponding borinic acid ( 2 ). This sequence can be performed in one pot to allow the facile, metal‐free conversion of an alkene into a small molecule containing a boron‐doped graphene substructure. Doubly boron‐doped perylene 2 exhibits visible range absorbance and fluorescence in chloroform solution ( Φ =0.63) and undergoes two reversible one‐electron reductions at moderate potentials of −1.30 and −1.64 eV vs. ferrocenium/ferrocene in DMSO. Despite sterically accessible boron centers and facile electrochemical reductions, compound 2 is air‐, moisture‐, and silica gel‐stable." @default.
- W2736458539 created "2017-07-31" @default.
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- W2736458539 date "2017-08-18" @default.
- W2736458539 modified "2023-10-17" @default.
- W2736458539 title "Synthesis of a Doubly Boron‐Doped Perylene through NHC‐Borenium Hydroboration/C−H Borylation/Dehydrogenation" @default.
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- W2736458539 doi "https://doi.org/10.1002/ange.201706346" @default.
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