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Flavylium Salts: A Blooming Core for Bioinspired Ionic Liquid Crystals
Authors:Robert Forschner  Jakob Knelles  Korinna Bader  Carsten Müller  Dr Wolfgang Frey  Prof Dr Andreas Köhn  Dr Yann Molard  Prof Dr Frank Giesselmann  Prof Dr Sabine Laschat
Institution:1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwalding 55, 70569 Stuttgart, Germany;2. Institut für Physikalische Chemie, Universität Stuttgart, Pfaffenwalding 55, 70569 Stuttgart, Germany;3. Institut für Theoretische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany;4. CNRS, ISCR-UMR6226, ScanMAT-UMS 2001, University Rennes, 35000 Rennes, France
Abstract:Thermotropic ionic liquid crystals based on the flavylium scaffold have been synthesized and studied for their structure-properties relationship for the first time. The mesogens were probed by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD). Low numbers of alkoxy side chains resulted in smectic (SmA) and lamello-columnar (LamCol) phases, whereas higher substituted flavylium salts showed Colro as well as ordered and disordered columnar (Colho, Colhd) mesophases. Mesophase width ranged from 13 K to 220 K, giving access to room temperature liquid crystals. The optical properties of the synthesized compounds were probed towards absorption and emission properties. Strong absorption with maxima between 444 and 507 nm was observed, and some chromophores were highly emissive with quantum yields up to 99 %. Ultimately, mesogenic and dye properties were examined by temperature-dependent emissive experiments in the solid state.
Keywords:fluorescence  ionic liquid crystals  self-assembly  UV/Vis spectroscopy  X-ray diffraction
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