Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stability
Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stability
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DOI：
10.1039/b615545f
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发表时间：
2007-01-01
影响因子：
--
通讯作者：
Kaszynski, Piotr
中科院分区：
文献类型：
--
作者：
Sienkowska, Monika J.;Farrar, John M.;Kaszynski, Piotr
利用热分析、光学分析、光谱分析和粉末XRD分析研究了一系列密切相关的苯并[c]噌啉（1）、四氮杂芘（2）、菲（3）和芘（4）的四取代衍生物的介晶性质。只有三个3，4-二辛氧基苯基衍生物表现出介晶性质。N取代CH（3 -> 1和4 -> 2对）以及核心元件尺寸的增加（1 -> 2和3 -> 4对）显著增加了中间相稳定性。的结果和观察到的趋势进行了合理化的构象特性，其中包括计算的平面化能，脂肪链密度和填充分数的建模分析。分子轨道计算表明，四氮杂衍生物2c是显着的缺电子和电子导电材料的适用。
A series of closely related tetrasubstituted derivatives of benzo[c] cinnoline (1), tetraazapyrene (2), phenanthrene (3), and pyrene (4) were investigated for their mesogenic properties using thermal, optical, spectroscopic, and powder XRD analyses. Only three 3,4-dioctyloxyphenyl derivatives exhibited mesogenic properties. Substitution of N for CH (3 -> 1 and 4 -> 2 pairs) and also increase of the core element size (1 -> 2 and 3 -> 4 pairs) significantly increases the mesophase stability. The findings and observed trends were rationalized by analysis of conformational properties which included calculation of the planarization energy, and modeling of aliphatic chain density and fill fractions. MO calculations showed that the tetraaza derivative 2c is significantly electron deficient and suitable for electron conductive materials.