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    188宝金博页面版: Synthesis and mesomorphic behavior of benzothiazole-based liquid crystals having terminal methoxyl group

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    内容提示： ＣＨ ＿ Ｎ Ｅ５ＥReceived 11 May 2009口ＨＥＭ ＿ ＣＡ Ｌprerequisite in designing new thermotropic liquid crystals [3]. An earlier report has shown that the introduction ofheterocycles as the central core greatly influenced the mesomorphic properties of the calamatic molecules owing totheir unsaturation and/or their more polarizable nature [4–7]. It has been reported that benzothiazole-based liquidcrystals possessed good hole-transporting properties with a low ionization potential, making them ofpotential interestas hole-transportin...

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    ＣＨ ＿ Ｎ Ｅ５ＥReceived 11 May 2009口ＨＥＭ ＿ ＣＡ Ｌprerequisite in designing new thermotropic liquid crystals [3]. An earlier report has shown that the introduction ofheterocycles as the central core greatly influenced the mesomorphic properties of the calamatic molecules owing totheir unsaturation and/or their more polarizable nature [4–7]. It has been reported that benzothiazole-based liquidcrystals possessed good hole-transporting properties with a low ionization potential, making them ofpotential interestas hole-transporting materials in organic light emitting devices (OLEDs) [8]. In our previous studies [9], abenzothiazole ring was incorporated as a mesogenic core in thermotropic liquid crystals which enabled themto exhibitgood mesomorphic properties.In order to further explore the benzothiazole as a mesogenic core in Schiffbase liquid crystals, here, we reported anew homologous series of 6-methoxy-2-(4-alkanoyloxybenzylidenamino)benzothiazoles and their synthetic route isillustrated in Scheme 1. 2-Amino-6-methoxybenzothiazole was condensed with 4-hydroxybenzaldehyde uponrefluxing in ethanol for 3 h following which the particular Schiff base intermediate was subjected to SteglichＬ Ｅ Ｔ Ｔ ＥＲ ５doi:10.1016/j.cclet.2009.06.023Synthesis and mesomorphic behavior of benzothiazole-based liquidcrystals having terminal methoxyl groupSie Tiong Haa,*, Teck Ming Kohb, Siew Teng Onga, Yasodha SivasothycaDepartment ofChemical Science, Faculty ofScience, Engineering & Technology, Universiti Tunku Abdul Rahman,Jln Universiti, Bandar Barat, 31900 Kampar, Perak, MalaysiabDepartment ofScience, Faculty ofEngineering & Science, Universiti Tunku Abdul Rahman, Jln Genting Klang,Setapak, 53300 Kuala Lumpur, MalaysiacChemistry Department, Faculty ofScience, Universiti Malaya, 50603 Kuala Lumpur, MalaysiaAbstractA homologous series ofbenzothiazole derivatives, 6-methoxy-2-(4-alkanoyloxybenzylidenamino)benzothiazoles, were synthe-sized and characterized using FT-IR,1H and13C NMR, mass spectrometry and elemental analysis. Enantiotropic nematic phase wasobserved throughout the entire series. Smectic C phase only emerged from the decanoyloxy derivative onwards. The terminalmethoxyl group and the ester linkage influenced the mesomorphic behavior of the present series.# 2009 Sie Tiong Ha. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.Keywords: Benzothiazole; Schiff bases; Nematic; Smectic C; Liquid crystalLiquid crystalline phase was first reported during the 19th century by the Austrian botanist Friedrich Reinitzerfromhis microscopic observation on the thermal behavior of molten cholesteryl benzoate [1]. This observation led to thediscovery of a new and fascinating class of soft materials which combines extraordinary optical, elastic and viscousproperties [2]. Selection of a mesogenic core, terminal groups and a suitable length of the flexible chains is thewww.elsevier.com/locate/ccletAvailable online at www.sciencedirect.comChinese Chemical Letters 20 (2009) 1449–1452* Corresponding author.E-mail addresses: hast_utar@yahoo.com, hast@utar.edu.my (S.T. Ha).1001-8417/$ –see front matter # 2009 Sie Tiong Ha. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.万方数据

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