Unique redox switching of orthoquinone-containing pentacyclic aromatic compounds with molecular hydrogen and oxygen in the presence of a palladium nanoparticle catalyst (SAPd) is disclosed. These molecules were predicted by in silico screening before synthesis. Efficient protocols for the synthesis of orthoquinone-containing aromatic compounds by palladium-mediated homocoupling and the benzoin condensation reaction were developed. Clear switching between orthoquinone and aromatic hydroquinone compounds was observed on the basis of their photoluminescence properties. Furthermore, the twist strain of the orthoquinone moiety could induce dramatic changes in color and emission.
The prologue and progress of π-electronic ion-pairing assemblies, including synthesis of π-electronic ions, preparation of ion pairs, fabrication of assemblies as crystals, gels and liquid crystals and their characteristic properties, are summarized.
Intramolecular aromatic C−N bond formation reactions using electron-rich aromatic tethered boron-masking N-hydroxyamide as substrate were realized. These new C−N bond formation reactions involve the in situ generation of a diaryliodonium salt by treatment with hypervalent iodine, deborylation by base treatment, spontaneous N → O acyl migration, cyclization, reductive elimination, elimination of benzoic acid, and tautomerization to indole formation. Hereby, we obtained highly functionalized electron-rich indoles and quinoline in practical yields.
[38]Octaphyrin(1.1.1.1.1.1.1.1) bearing four methyl moieties at the inner nitrogen sites has been synthesized and exhibited chiroptical properties and dynamic conversions.
α-Ketocarbenium ions derived from synthesized orthoquinone-containing polycyclic aromatic compounds were generated in the presence of Brønsted acids such as sulfuric acid, trifluoromethanesulfonic acid, and fluorosulfonic acid. The prepared α-ketocarbenium ions were stabilized by conjugation of the aromatic moiety. In addition, unique absorption properties of the α-ketocarbenium ions were observed and identified on the basis of the calculated absorption spectra. It was suggested that the zigzag-shaped architecture stabilizes the newly discovered α-ketocarbenium ions derived from orthoquinone-containing polycyclic aromatic compounds.
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