Synthesis and Characterization of Liquid-Crystalline Tetraoxapentacene Derivatives Exhibiting Aggregation-Induced Emission
Autor: | Kenneth E. Maly, Brooke M. Raycraft, Monika Wałęsa-Chorab, S. Holger Eichhorn, William G. Skene, Louise N. Dawe, Coralie Cambe, Alexandre Malinge, Hi Taing, Lana K. Hiscock |
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Rok vydání: | 2018 |
Předmět: |
Chemistry
Organic Chemistry 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Catalysis 0104 chemical sciences law.invention chemistry.chemical_compound Crystallography Differential scanning calorimetry Optical microscope law Terphenyl Excited state Side chain Molecule Thin film 0210 nano-technology Luminescence |
Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 25(4) |
ISSN: | 1521-3765 |
Popis: | A series of new tetrakis(dialkoxyphenyl) dicyanotetraoxapentacene derivatives (1 a-c) were prepared by reaction of the appropriate terphenyl diols with tetrafluoroterephthalonitrile in good yields. Compounds 1 b and 1 c, which bear hexyloxy and decyloxy side chains, exhibited columnar hexagonal mesophases, as shown by polarized optical microscopy, variable-temperature powder X-ray diffraction, and differential scanning calorimetry. Single-crystal X-ray diffraction of methoxy-substituted 1 a revealed that the dicyanotetraoxapentacene core is highly planar, consistent with the notion that these molecules are able to stack in columnar mesophases. A detailed photophysical characterization showed that these compounds exhibit aggregation-induced emission in solution, emission in nonpolar solvents, weak emission in polar solvents, and strong emission in the solid state both as powder and in thin films. These observations are consistent with a weakly emissive charge-transfer state in polar solvents and a more highly emissive locally excited state in nonpolar solvents. |
Databáze: | OpenAIRE |
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