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s-Triazine-Based Functional Discotic Liquid Crystals: Synthesis, Mesomorphism and Photoluminescence

机译:基于s-三嗪的功能性盘状液晶:合成,同构和光致发光

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摘要

A new series of C-3-symmetric, pi-conjugated molecules was designed, synthesized and characterized. The materials were derived from electron-accepting s-triazine, appended covalently to electron-donating styrylbenzene arms, and were readily prepared in excellent yield with high purity by means of threefold condensation of triphosphonate with n-alkoxybenzaldehydes under Horner-Wadsworth-Emmons reaction conditions. Examination of the phase transitional properties by several complementary techniques evidenced self-assembly into a hexagonal columnar phase, occurring over wide and reasonable thermal ranges. The photophysical properties were studied both in solution and in the fluid/frozen columnar states by UV/Vis absorption and photoluminescence spectroscopy. The emission spectra obtained as a function of the temperature rule out the breaking-up of larger columns and a non-radiative, thermally activated process. A study carried out on thin films of the glassy columnar state, which accounts for conserved fluorescence, defect-free orientation, and freezing ionic species, with the help of atomic force microscopy (AFM) images, suggested a homogeneous granular morphology comprising fibrillar structures. Dissimilarities in the surface morphology and birefringence of thin films of the solid and frozen columnar states were clearly shown by Raman spectroscopy. An electrochemical investigation revealed a LUMO energy of -4.0 eV. Thus, the discotic motifs presented herein meet certain criteria of organic materials, which are essential for developing electronic devices.
机译:设计,合成和表征了一系列新的C-3-对称,π共轭分子。该材料衍生自电子接受性的三嗪,共价附于给电子的苯乙烯基苯臂上,并易于在霍纳-沃兹沃思-埃蒙斯反应条件下通过三膦酸酯与正烷氧基苯甲醛的三倍缩合以高收率和高纯度轻松制备。 。通过几种互补技术对相变性质的研究证明了自组装成六方柱状相的情况,发生在较宽和合理的温度范围内。通过UV / Vis吸收和光致发光光谱学研究了溶液和流体/冻结柱状状态下的光物理性质。根据温度获得的发射光谱排除了较大色谱柱的破裂和无辐射的热活化过程。在原子力显微镜(AFM)图像的帮助下,对玻璃态柱状薄膜进行了研究,该薄膜解释了保守的荧光,无缺陷的取向和冻结的离子种类,并提出了包含纤维状结构的均匀颗粒形态。拉曼光谱法清楚地表明了固态和冷冻柱状薄膜的表面形态和双折射的差异。电化学研究显示LUMO能量为-4.0 eV。因此,本文呈现的盘状图案满足有机材料的某些标准,这对于开发电子设备是必不可少的。

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