Synthesis and liquid crystalline behavior of azulene-based liquid crystals with 6-hexadecyl substituents on each azulene ring

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• 作者：Kosuke Nakagawa ; Takahiro Yokoyama ; Kozo Toyota ; Noboru Morita ; Shunji Ito ; Shota Tahata ; Mao Ueda ; Jun Kawakami ; Miho Yokoyama ; Yoriko Kanai ; Kazuchika Ohta
• 关键词：Discotic liquid crystals ; Homeotropic alignment ; Azulenes ; Cyclotrimerization
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：16 October 2010
• 年：2010
• 卷：66
• 期：42
• 页码：8304-8312
• 全文大小：1024 K

文摘

Hexakis(6-hexadecyl-2-azulenyl)benzene (1b) has been synthesized by Co₂(CO)₈-catalyzed cyclotrimerization reaction of bis(6-hexadecyl-2-azulenyl)acetylene (2b). The mesomorphic behaviors of 1b, 2b, and 6-hexadecyl-2-phenylazulene (3b) were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD) techniques and their mesomorphic properties were compared with those of their 6-octyl derivatives 1a, 2a, and 3a. Increase of the number of carbon atoms in the peripheral side chains drops the isotropization temperatures of 1b, 2b, and 3b by 56.9 °C, 33 °C, and 23.6 °C, respectively. Additionally, the phase-transition behavior varied with increase of the number of the peripheral chains, as well as decrease of the crystalline–mesophase transition temperatures, except for compound 3b. As the results, spontaneous monodomain homeotropic molecular alignment was revealed by compound 1b in its Col_hd mesophase on non-treated glass substrate, which would be attracted to the application for the device fabrication of molecular materials.