Nitrogen-centered buckybowls with sulfur decoration at the rim were synthesized and characterized. The buckybowls demonstrate tunable properties depending on the state of the sulfur atom.

Triphenylamine functionalized acridone leads to a donor–acceptor system with intramolecular charge transfer process and tuneable aggregation induced enhanced emission.

Length‐defined 2,7‐acridone oligomers were synthesized via a sequence of bromination, borylation and Suzuki–Miyaura cross‐coupling reaction. Both the single crystal structure analysis and the theoretical calculations demonstrate that the anti conformation is favored in the oligomer. The relationship of the properties and the number of acridone units in the oligomer was investigated. The UV/Vis absorption and fluorescence spectroscopy reveal that the absorption and emission of oligomers are red‐shifted and energy gaps narrow with the increase of acridone moieties, as well as a decline in the radiative decay rate. Cyclic voltammetry measurements and theoretical calculations elucidate that the quantity of acridone in the oligomer plays a greater effect on the HOMO energy levels than on the LUMO ones.

Intramolecular electrophilic cyclization of a bisanthranilate afforded an angular cis-quinacridone compound, which condensed with hydrazine to give a phthalazine derivative. A [2+2+2] cyclization reaction occurred at the C–N double bond position of phthalazine when reacted with dimethyl acetylenedicarboxylate. The structures of these novel compounds were confirmed by crystallographic analysis. The phthalazine derivative decomposes back to quinacridone at ambient condition in the dark and as a solid with a half lifetime of about 22 months.

Methyl benzoate functionalized phenylenediamine derivatives with the methoxycarbonyl groups at the ortho-, meta-and para-positions of amino group were synthesized via palladiumcatalyzed Buchwald-Hartwig reaction and copper-catalyzed Ullmann amination. Crystallographic analysis unraveled the presences of intra-and intermolecular hydrogen bonds in compounds bearing NH groups. Spectroscopic investigation revealed that compounds with amine protected by phenyl showed varied emissions with relatively stronger intensity in solution and in solid state than those of the unprotected ones. All the compounds demonstrated aggregation induced enhanced emissions in THF/water, some of which exhibited tunable emissions according to the water contents. Theoretical calculations unveiled that compound with intramolecular hydrogen bond possessed twisted structure and could undergo one proton transfer process in the excited state, which were essential to its low fluorescence intensity in solution and enhanced emission in the solid state.