高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (7): 1203-1209.doi: 10.7503/cjcu20160877

• 有机化学 • 上一篇    下一篇

巴比妥酸楔形棒状液晶分子的合成、性质及与三嗪衍生物的氢键识别组装体

夏萌, 彭雄伟, 高红飞, 严超, 陈慧茹, 程晓红()   

  1. 云南大学教育部自然资源重点实验室, 化学科学与工程学院, 昆明 650091
  • 收稿日期:2016-12-05 出版日期:2017-07-10 发布日期:2017-04-13
  • 作者简介:联系人简介: 程晓红, 女, 博士, 教授, 博士生导师, 主要从事超分子化学研究. E-mail: xhcheng@ynu.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 21274119, 21364017, 21664015, 21602195)、 云南省应用基础研究计划青年项目(批准号: 2016FD008)、 云南大学研究生科研创新基金(批准号: YNUY201682)和云南省教育厅科学研究基金重大专项项目(批准号: ZD2015001)资助

Synthesis and Properties of Barbituric Acid Based Taper Shaped Rodlike Liquid Crystal Compound and Hydrogen Bonded Complex with Triazine Derivative

XIA Meng, PENG Xiongwei, GAO Hongfei, YAN Chao, CHEN Huiru, CHENG Xiaohong*()   

  1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
  • Received:2016-12-05 Online:2017-07-10 Published:2017-04-13
  • Contact: CHENG Xiaohong E-mail:xhcheng@ynu.edu.cn
  • Supported by:
    † Supported by the National Natural Science Foundation of China(Nos.21274119, 21364017, 21664015, 21602195), the Yunnan Natural Science Foundation Youth Projec, China(No.2016FD008), the Yunnan University Graduate Students Project, China(No YNUY201682) and the Yunnan Education Department Foundation Key Poject, China(No ZD2015001)

摘要:

合成了一端含巴比妥酸, 另一端含带三条烷基链苯甲酸酯楔形单元, 中间为苯乙烯共轭单元的棒状分子5-{4-[3,4,5-三(十二烷氧基)苯甲酸酯]苯乙烯}-(1H,3H)-2,4,6嘧啶三酮(BA3/12); 采用偏光显微镜(POM)、 示差扫描量热法(DSC)、 X射线衍射(XRD)、 扫描电子显微镜(SEM)、 红外光谱(IR)、 核磁共振波谱(NMR)和荧光光谱等对其进行了表征. 结果表明, BA3/12能自组装形成晶格结构为c2mm的长方柱相液晶; 红外光谱及核磁共振氢谱表征数据初步证实了BA3/12与三嗪化合物6-(5-{4-[3,4-双(十二烷氧基)]苄氧基}苯基)噻吩-2,4-二氨基-1,3,5三嗪(1T2/12)形成的等摩尔氢键复合物BA/T的结构; BA/T不仅具有液晶性质且能形成具有三维网络状结构的超分子凝胶.

关键词: 巴比妥酸, 氢键, 液晶, 有机凝胶, 荧光猝灭

Abstract:

A new kind of barbituric acid based taper shaped rodlike compound 4-{[2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene]methyl}phenyl-3,4,5-tris(dodecyloxy)benzoate(BA3/12), consisting of a styrene conjugate rodlike core with the barbituric acid at one end, and benzoate wedge unit with triple alkyl chain at the other end was synthesized. The properties were investigated with polarising optical microscopy(POM), differential scanning calorimetry(DSC), X-ray diffraction(XRD), scanning electron microscope(SEM), infrared spectrum(IR), nuclear magnetic resonance(NMR) spectroscopy and fluorescence emission spectrum. Compound BA3/12 can self-assemble into columnar liquid crystalline(LC) phase with c2mm lattice. The structure of complex BA/T between BA3/12 and triazine 6-[5-(4-{[3,4-bis(dodecyloxy)benzyl]oxy}phenyl)thiophen-2-yl]-1,3,5-triazine-2,4-diamine(1T2/12) was initially identified via IR and 1H NMR. This complex BA/T showed both liquid crystalline property in its pure state and supramolecular organogels with three-dimensional networks in organic solvents.

Key words: Barbituric acid, H-Bonding, Liquid crystal, Organogel, Fluorescence quenching

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