Tetrakis(oxadiazolylphenyl)pyrazines: New St. Andrew′s Cross-Shaped Liquid Crystals
Dr. Nico Röder
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorDr. Tomasz Marszalek
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
Search for more papers by this authorDaniel Limbach
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorCorresponding Author
Prof. Wojciech Pisula
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
Search for more papers by this authorCorresponding Author
Prof. Heiner Detert
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorDr. Nico Röder
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorDr. Tomasz Marszalek
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
Search for more papers by this authorDaniel Limbach
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorCorresponding Author
Prof. Wojciech Pisula
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
Search for more papers by this authorCorresponding Author
Prof. Heiner Detert
Institute for Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10–14, 55118 Mainz, Germany
Search for more papers by this authorDedicated to Prof. Gerhard Wenz on the occasion of his retirement
Graphical Abstract
Tetraphenylpyrazine is the core of a new series of electron-deficient fluorophores. Fourfold Huisgen reaction with tetrazoles generates the diaryl-1,3,4-oxadiazole arms with alkoxy chains in the periphery. The saddle-shaped molecules assemble to columns. When alkoxy chains of 4 - 16 carbons are attached, the molecules form broad mesophases up to 246°C and typically self-assemble in hexagonal columnar superstructures.
Abstract
π-Conjugated molecules with the shape of St. Andrew′s cross have been synthesized via fourfold Huisgen reaction. Four 2,5-diaryl-1,3,4-oxadiazol arms are attached to a central pyrazine nucleus. These fluorescent stars, when decorated with a rim of eight alkoxy side chains are discotic liquid crystals. Depending on the substitution pattern, the width of the liquid phase varies within a broad range of 25 °C to 250 °C. In their liquid crystalline phase, the molecules assemble in a typical hexagonal columnar supramolecular arrangement.
Conflict of interest
The authors declare no conflict of interest.
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