Fluorescent organic single crystals with elastic bending flexibility: 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene derivatives
| Autor: | Natsumi Kamiya, Toshio Koizumi, Yoshinobu Yokomori, Takuto Maeda, Shotaro Hayashi, Atsushi Asano |
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| Rok vydání: | 2017 |
| Předmět: |
Multidisciplinary
Materials science 010405 organic chemistry lcsh:R lcsh:Medicine Crystal structure Bending 010402 general chemistry 01 natural sciences Fluorescence Article 0104 chemical sciences law.invention Crystal Stress (mechanics) Crystallography Molecular wire Lamella (surface anatomy) law lcsh:Q Crystallization lcsh:Science |
| Zdroj: | Scientific Reports Scientific Reports, Vol 7, Iss 1, Pp 1-10 (2017) |
| ISSN: | 2045-2322 |
| Popis: | Organic single crystals with elastic bending flexibility are rare because they are generally brittle. We report here fluorescent organic single crystals based on thiophene-tetrafluorobenzene-thiophene derivatives, mainly 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene. Three derivatives were synthesized by Pd-catalyzed cross-coupling reactions (Stille or direct arylation pathways). The crystallization of the derivatives gave large (mm- or cm-scale) crystals. Two crystals of 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene, 1, and 1,4-bis(4-methylthien-2-yl)-2,3,5,6-tetrafluorobenzene, 3, bent under applied stress and quickly recovered its original shape upon relaxation. The other crystal of 1,4-bis(5-methylthien-2-yl)-2,3,5,6-tetrafluorobenzene, 2, showed brittle breakage under applied stress (normal behavior). Fibril lamella crystal structure based on criss-cross packed slip-stacked molecular wires and its structural integrity are important factors for the design and production of next generation crystal materials with elastic bending flexibility. Furthermore, mechanical bending–relaxation resulted in reversible change of the morphology and fluorescence (mechanofluorochromism). Such bendable crystals would lead to the next generation solid-state fluorescent and/or semiconducting materials. |
| Databáze: | OpenAIRE |
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