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2-Chloroalkoxy-Substituted Pentafluorinated Bistolanes as Novel Light-Emitting Liquid Crystals

Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
Department of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Naka-narusawa, Hitachi, Ibaraki 316-8511, Japan
Author to whom correspondence should be addressed.
Crystals 2019, 9(4), 195;
Received: 19 March 2019 / Revised: 2 April 2019 / Accepted: 3 April 2019 / Published: 6 April 2019
(This article belongs to the Special Issue Synthesis and Properties of Light-emitting Liquid Crystals)
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In this study, we designed and synthesized novel pentafluorinated bistolane derivatives with 2-chloropentyl or 2-chlorohexyl flexible units as novel light-emitting liquid crystals (LELCs). By measuring the phase-transition behaviors, all derivatives were found to display liquid-crystalline (LC) phases during both heating and cooling processes. Among the novel bistolanes, the S- and R-configured derivatives exhibited a chiral nematic (N*) phase with a typical Grandjean optical texture. Interestingly, the chiral derivatives also exhibited a blue phase with a typical platelet texture in a narrow temperature range (2–4 °C). Photophysical measurements revealed that the 2-chloroalkoxy-substituted pentafluorinated bistolanes exhibited intense photoluminescence (PL) both in solution and in crystalline phases. The PL characteristics, especially the maximum PL wavelength, were found to switch sensitively during the heating and cooling cycles depending on the molecular aggregates through the crystal (Cr) ⇄ N* phase transition. The 2-chloroalkoxy flexible units induced dynamic changes in the LC and PL properties, providing valuable insight into the potential of various LELCs as PL sensing materials. View Full-Text
Keywords: liquid crystal; photoluminescence; fluorine; bistolane structure; chirality liquid crystal; photoluminescence; fluorine; bistolane structure; chirality

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Yamada, S.; Miyano, K.; Agou, T.; Kubota, T.; Konno, T. 2-Chloroalkoxy-Substituted Pentafluorinated Bistolanes as Novel Light-Emitting Liquid Crystals. Crystals 2019, 9, 195.

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