11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)-undecanol | 391881-60-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)-undecanol
• 英文别名: 11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)undecanol；11-(1,1,3,3,5,5,5-heptamethyltrisiloxanyl)undecanol；11-(1,1,1,3,3,5,5-hetamethyltrisiloxanyl)undecanol；(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)undecanol；Me3SiO(Me)2SiO(Me)2Si(CH2)11OH；11-[[Dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]undecan-1-ol
• CAS: 391881-60-0
• 化学式: C₁₈H₄₄O₃Si₃
• 分子量: 392.802
• InChiKey: ODKBWDNYFUWQLA-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±34.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)-undecanol 在 偶氮二甲酸二异丙酯 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(4-octyloxyphenyl)-5-[11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)undecyloxy]pyrimidine
  参考文献：
  名称：

  Siloxane-terminated phenylpyrimidine liquid crystal hosts

  摘要：

  我们报告了以三硅氧烷为端基、以 2-苯基嘧啶为核心、形成部分双层 SmA 和 SmC 相的液晶的合成和表征。通过粉末 X 射线衍射法对 Smectic 层间距的变温测量、光学倾斜角的测量以及偏光光学显微镜对双折射变化的观察发现，与非硅氧烷类似物相比，三硅氧烷端基使这些化合物的 SmA-SmC 转变更加 "类似德弗里斯"。其中一种化合物是 2-(4-(11-(1,1,1,3,3,5,5-庚甲基三硅氧烷基)十一烷氧基)苯基)-5-(1-氯辛氧基)嘧啶 (3)，其最大层收缩率仅为 1.6%，可视为真正的 de Vries 材料。

  DOI：

  10.1039/b700972k
• 作为产物：
  描述：

  10-十一烯-1-醇 、 1,1,1,3,3,5,5-七甲基三硅氧烷 在 platinum-containing catalyst 作用下， 生成 11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)-undecanol
  参考文献：
  名称：

  Fast switching organosiloxane ferroelectric liquid crystals

  摘要：

  我们报道了具有手性 (R,R)-2,3-二氟辛氧基侧链的有机硅氧烷 2-苯基嘧啶介晶的合成和表征。这些化合物形成手性 SmA* 和 SmC* 相，并作为表面稳定的铁电液晶表现出卓越的电光和取向特性，包括最快的光学上升时间之一（T − TAC = -10 K 和 6 V 时为 11 µs） µm−1) 为有机硅氧烷介晶。

  DOI：

  10.1039/b810209k

文献信息

• Thioindigo-containing organosiloxane liquid crystals with electroclinic properties
  作者：Jason Z. Vlahakis、Kenneth E. Maly、Robert P. Lemieux

  DOI：10.1039/b103755m

  日期：——

  Two mesogenic thioindigo derivatives containing oligomeric di- and trisiloxane end-groups were synthesized in optically pure form. These materials form enantiotropic SmA* liquid crystal phases over temperature ranges of 120–143 °C and 110–146 °C, respectively, and exhibit electroclinic switching. The electroclinic coefficient for the trisiloxane derivative at T − TC = 8 K is 0.4° V−1 µm−1. The formation of a SmA* phase by these thioindigo derivatives is due primarily to the tendency of siloxane and paraffinic moieties to micro-segregate into distinct sublayers within a lamellar structure. To the best of our knowledge, these are the first two examples of thioindigo-containing liquid crystals to be reported in the literature.

  我们合成了两种含有低聚二硅氧烷和三硅氧烷末端基团的中生硫代靛蓝衍生物的光学纯品。这些材料分别在 120-143 ℃ 和 110-146 ℃ 的温度范围内形成对映的 SmA* 液晶相，并表现出电致冷转换。在 T - TC = 8 K 时，三硅氧烷衍生物的电clinic系数为 0.4° V-1 µm-1。这些硫代靛蓝衍生物之所以能形成 SmA* 相，主要是因为硅氧烷和石蜡分子倾向于在层状结构中微观分离成不同的亚层。据我们所知，这是文献中首次报道的含硫代靛蓝液晶的两个实例。
• Tuning the frustration between SmA- and SmC-promoting elements in liquid crystals with ‘de Vries-like’ properties
  作者：Qingxiang Song、Dorothee Nonnenmacher、Frank Giesselmann、Robert P. Lemieux

  DOI：10.1039/c1cc10344j

  日期：——

  Smectic liquid crystals with ‘de Vries-like’ properties are characterized by a maximum layer contraction of ≤1% upon transition from the non-tilted SmA phase to the tilted SmC phase. We show herein that one can systematically increase the ‘de Vries-like’ character of a smectic liquid crystal by tuning the frustration between SmA- and SmC-promoting elements according to established structure–property relationships.

  具有 "类德弗里斯 "特性的Smectic液晶在从非倾斜SmA相过渡到倾斜SmC相时，最大层收缩率为±1%。我们在此表明，根据已建立的结构-性能关系，通过调整SmA促进元素和SmC促进元素之间的沮度，可以有计划地提高Smectic液晶的 "类德弗里斯 "特性。
• Design of Liquid Crystals with “de Vries-like” Properties: Frustration between SmA- and SmC-Promoting Elements
  作者：Jeffrey C. Roberts、Nadia Kapernaum、Qingxiang Song、Dorothee Nonnenmacher、Khurshid Ayub、Frank Giesselmann、Robert P. Lemieux

  DOI：10.1021/ja9087727

  日期：2010.1.13

  According to a new design strategy for "de Vries-like" liquid crystal materials, which are characterized by a maximum layer contraction of <= 1% upon transition from the SmA phase to the SmC phase, we report the synthesis and characterization of two homologous series of organosiloxane mesogens. The design of these new materials is based on a frustration between one structural element that promotes the formation of a SmC phase (a trisiloxane-terminated side-chain) and one that promotes the formation of a SmA phase (either a chloro-terminated side-chain or a 5-phenylpyrimidine core). Measurements of smectic layer spacing d as a function of temperature by small-angle X-ray scattering (SAXS) combined with optical tilt angle measurements revealed that the mesogens 5-(4-(11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)-undecyloxy)phenyl)-2-(1-alkyloxy)pyrimidine (3(n)) undergo SmA-SmC phase transitions with maximum layer contractions ranging from 0.5% to 1.4%. A comparison of reduction factors R and f suggests that this behavior is due in part to a pronounced negative thermal expansion in the SmC phase that counterbalances the layer contraction caused by increasing tilt. SAXS measurements also revealed that compounds 3(n) are characterized by low orientational and high translational order, which is consistent with theoretical predictions that such materials should exhibit de Vries-like properties. The R values for series 3(n) are comparable to, and even lower than, those reported for established de Vries-like materials such as the perfluorinated 2-phenylpyrimidine material 3M 8422.