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...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-05, Vol.2014 (15), p.3116-3126
Main Authors: Glang, Stefan, Rieth, Thorsten, Borchmann, Dorothee, Fortunati, Ilaria, Signorini, Raffaella, Detert, Heiner
Format: Article
Language:English
Subjects:
Chromophores
Conjugated oligomers
Fluorescence
Heterocycles
Liquid crystals
Nonlinear optics
Optical properties
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Summary: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. Star‐shaped and dendritic molecules with a triphenyl‐tristriazolotriazine core and flexible side chains are prepared from tetrazoles and cyanuric chloride. The optical, nonlinear optical, and thermotropic properties of these compounds as well as their phenylethynyl homologues are reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201400088