2,4,5,7,9,10-Hexaethynylpyrenes: Synthesis, Properties, and Self-Assembly.

A series of 2,4,5,7,9,10-hexaethynylpyrenes was synthesized using 2,7,9,10-tetrabromopyrene-4,5-dione as the key intermediate. The effects of the position and number of the ethynyl groups on the physicochemical properties of the corresponding pyrenes were clarified by comparison with 4,5,9,10-tetraethynylpyrene and 2,7-diethynylpyrene derivatives. The prepared hexaethynylpyrenes that bear benzene moieties self-assemble via π-π stacking in solution and/or the condensed phase.

Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: synthesis, photophysical and electrochemical properties, and self-assembly behavior.

We report the synthesis, photophysical properties, redox characteristics, and self-assembly behavior of disk-shaped trithiazolyl-1,3,5-triazines that bear decyloxybenzene moieties. These compounds were synthesized by a Migita-Kosugi-Stille coupling reaction of 1,3,5-trichlorotriazine with three different tributyltin(thiazoles) as the key step. The structure-property relationships, namely the effects of the incorporation of thiazole units into the triazine unit, the conjugation connectivity between the thiazole and triazine units, and the insertion of ethynylene spacers between the thiazole and decyloxybenzene moieties on the properties of the trithiazolyl-1,3,5-triazines were comprehensively investigated.