0000000000464837
AUTHOR
Dorothee Borchmann
Tristriazolotriazines with π-Conjugated Segments: Star-Shaped Fluorophors and Discotic Liquid Crystals
C3-symmetrical tristriazolotriazines substituted with phenylene rings carrying lateral flexible alkoxy side chains were prepared via condensation/ring transformation of cyanuric chloride and tetrazoles. These star-shaped, planar compounds can form broad thermotropic mesophases. Due to the extensive π-conjugation, these compounds are highly emissive and the octupolar donor-acceptor electronic structure results in non-linear optical properties like solvatochromism. Brønstedt acids provoke halochromism of the absorption and of the fluorescence.
Arylethynyl-Substituted Tristriazolotriazines: Synthesis, Optical Properties, and Thermotropic Behavior
The synthesis of C3-symmetrical tristriazolotriazines with conjugated arms and lateral alkoxy side chains was performed by a threefold condensation of cyanuric chloride with tetrazoles. Conjugated π segments include phenyl, tolane, and its phenylethynyl-elongated homologue. Disclike and a dendritic molecule have been obtained, and two compounds with a 3,4,5-tris(octyloxy) substitution form broad thermotropic mesophases. The linear optical properties, solvatochromism of the fluorescence, acidochromism, and the two-photon absorption efficiency of selected compounds are reported.
3,5-Dialkoxy Substituted Triphenyl-tristriazolotriazines: Fluorescent Discotic Liquid Crystals
Tristriazolotriazines with a threefold 3,5-dialkoxyphenyl substitution were prepared from the corresponding phenyltetrazoles and cyanuric chloride. These star-shaped compounds are discotic liquid crystals that form broad and stable thermotropic mesophases. The thermal behaviour was studied by DSC and polarizing optical microscopy. An increasing length of the side chains reduces the phase transition temperatures, this effect is more pronounced for the crystalline to mesophase transition than for the clearing temperature. XRD on an oriented sample revealed a hexagonal columnar structure for the mesophase. All TTTs emit a strong fluorescence in the UV-violet region.