4'-(10-undecenyl-1-oxy)-4-biphenol | 123640-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-(10-undecenyl-1-oxy)-4-biphenol
• 英文别名: 4-hydroxy-(4'-undec-10-enyloxy)biphenyl；4'-(undec-10-enyloxy)biphenyl-4-ol；4-(10-undecenyloxy)biphenyl-4'-ol；4'-hydroxybiphenyl undecene-1-yl ether；4'-Undec-10-enyloxy-biphenyl-4-ol；4-(4-undec-10-enoxyphenyl)phenol
• CAS: 123640-26-6
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: YRSQHMLDGTWCLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(10-undecenyl-1-oxy)-4-biphenol 在 4-二甲氨基吡啶 、 四甲基二乙烯基二硅氧烷 、 N,N'-二环己基碳二亚胺 、 铂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 4'-((11-(1,1,3,3,3-pentamethyldisiloxaneyl)undecyl)oxy)-[1,1'-biphenyl]-4-yl (2S,3S)-2-chloro-3-methylpentanoate
  参考文献：
  名称：

  Synthesis and Characterization of Ferroelectric Liquid Crystalline Siloxanes Containing 4-Hydroxyphenyl(2S,3S)-2-Chloro-3-Methylvalerate

  摘要：

  New series of organosiloxane ferroelectric liquid crystalline materials have been synthesized, and their mesomorphic and physical properties have been characterized. These new series contain bis-siloxane or tris-siloxane unit attached to the flexible alkyl chain end of (2S,3S)-2-chloro-3-methylvalerate. The siloxane molecule induction is helpful to the chiral smectic C (S-C*) formation and chiral S-C* stabilization, and it simultaneously causes the liquid crystal temperature range of chiral S-C* to be broader. The siloxane member is helpful in reducing the smectic C (S-C) transation shift temperature, and the molecule containing tris-siloxane units shows better effect than the bis-siloxane one. The synthesis and characterization of the new FLCs materials which exhibit S-C* phase at room temperature and higher spontaneous polarization are presented.

  DOI：

  10.1080/15421406.2011.599204
• 作为产物：
  描述：

  1,11-二溴十一烷 在 potassium iodide 、 potassium hydroxide 、 三(二甲胺基)膦 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4'-(10-undecenyl-1-oxy)-4-biphenol
  参考文献：
  名称：

  Synthesis and Characterization of Ferroelectric Liquid Crystalline Siloxanes Containing 4-Hydroxyphenyl(2S,3S)-2-Chloro-3-Methylvalerate

  摘要：

  New series of organosiloxane ferroelectric liquid crystalline materials have been synthesized, and their mesomorphic and physical properties have been characterized. These new series contain bis-siloxane or tris-siloxane unit attached to the flexible alkyl chain end of (2S,3S)-2-chloro-3-methylvalerate. The siloxane molecule induction is helpful to the chiral smectic C (S-C*) formation and chiral S-C* stabilization, and it simultaneously causes the liquid crystal temperature range of chiral S-C* to be broader. The siloxane member is helpful in reducing the smectic C (S-C) transation shift temperature, and the molecule containing tris-siloxane units shows better effect than the bis-siloxane one. The synthesis and characterization of the new FLCs materials which exhibit S-C* phase at room temperature and higher spontaneous polarization are presented.

  DOI：

  10.1080/15421406.2011.599204

文献信息

• Organic–inorganic hybrid liquid crystals derived from octameric silsesquioxanes. Effect of the peripheral groups in mesogens on the formation of liquid crystals
  作者：Xiaobai Wang、Ching Mui Cho、Wan Yong Say、Angeline Yan Xuan Tan、Chaobin He、Hardy Sze On Chan、Jianwei Xu

  DOI：10.1039/c0jm03406a

  日期：——

  A series of octameric silsesquioxane-based organic–inorganic hybrid compounds 7a–h was synthesised by reacting octakis(dimethylsiloxy)silsesquioxane with 4′-(undec-10-enyloxy)biphenyl-4-yl mono-, di-, or trialkoxybenzoateviaplatinum-catalysed hydrosilylation reaction. The chemical structures of 7a–h were characterised by 1H, 13C, and 29Si nuclear magnetic resonance spectroscopy, mass spectroscopy and elemental analysis. Liquid crystallinity of 7a–h was investigated by differential scanning calorimetry (DSC) and polarised optical microscopy (POM). Temperature-dependent X-ray diffraction was used to verify liquid crystal phases, revealing that 7a–d assembled to smectic C and smectic A phases. The effects of the number and length of peripheral flexible alkoxy groups in 7a–h on the formation of liquid crystals were studied using DSC and POM, which revealed that 7a–d bore one alkoxy terminal group in each mesogen exhibited a mesophase, 7e–f and 7g–h bore two and three flexible alkoxy terminal groups in each mesogen, respectively, and did not show mesomorphic behaviour. The concept of “flexible group density” (FGD), which was defined as the number of the CH2 groups per unit volume in the periphery of the POSS molecule, was introduced to interpret the formation of liquid crystals. The results revealed that the POSS molecules with di- and tri-substituted mesogens exhibited much larger FGD than those with mono-substituted mesogens, hence the absence of mesophases for 7e–f and 7g–h. This study provides a useful archetype to predict the formation of liquid crystals when designing and synthesising liquid crystalline materials, particularly star-like or dendrimer-like molecular materials.

  通过八甲基环四硅氧烷与4′-（十一碳-10-烯氧基）联苯-4-基单、二或三烷氧基苯甲酸酯在铂催化硅氢加成反应中合成了系列八聚体硅倍半氧烷基有机-无机杂化化合物7a～7h。通过核磁共振光谱、质谱和元素分析对7a～7h的化学结构进行了表征。利用差示扫描量热法（DSC）和偏光显微镜（POM）研究了7a～7h的液晶性。采用温度依赖的广角X射线衍射法确认液晶相，结果表明7a～7d形成近晶C相和近晶A相。通过DSC和POM研究了7a～7h分子周围末端柔性烷氧基的数量和长度对液晶形成的影响，结果表明7a～7d每个介晶基元中有一个末端烷氧基，具有液晶相。7e～7f有二个、7g～7h有三个柔性烷氧基团。在每个介晶基元中没有呈现液晶行为。提出了“柔性基团密度”（FGD）这一概念，定义为POSS分子周围每单位体积中的CH2基数量，来解释液晶的形成。结果表明，双、三取代的介晶基元的FGD远大于单取代介晶基元的FGD，因此，7e～7f和7g～7h未形成液晶相。该研究表明，FGD可作为设计和合成的液晶材料，特别是星形或树枝状分子材料形成液晶性的预测参数。
• Ferroelectric-like behaviour of the SmCP phase in liquid crystalline compounds with asymmetrical bent-core molecules
  作者：V. Novotná、M. Kašpar、V. Hamplová、M. Glogarová、L. Lejček、J. Kroupa、D. Pociecha

  DOI：10.1039/b601084a

  日期：——

  A new series of asymmetrical bent-shaped mesogens has been synthesised and their mesomorphic properties studied. All compounds exhibit the B2 (SmCP) phase. For some compounds we found a very low coercive field for switching to the saturated ferroelectric state and only one peak in the switching current. Due to the lack of SHG signal in the zero field state and the behaviour of the relaxation mode we cannot unambiguously assign ferroelectric or antiferroelectric character to the B2 phase observed. The observation of planar samples revealed a striped texture. Large optically active domains appear on very slow cooling, which are attributed to a non-homogeneous (twisted) in-plane structure imposed by surfaces. The twisted domains are suppressed under a critical electric field. A simple model of such a structure and its behavior in the electric field is proposed. The low temperature phase detected on further cooling is attributed to a crystalline-like smectic phase.

  我们合成了一系列新的不对称弯曲状介质，并研究了它们的介质性质。所有化合物都呈现出 B2（SmCP）相。对于某些化合物，我们发现切换到饱和铁电态的矫顽力场非常低，而且切换电流只有一个峰值。由于在零磁场状态下缺乏 SHG 信号以及弛豫模式的行为，我们无法明确地为观察到的 B2 相赋予铁电或反铁电特性。对平面样品的观察显示出一种条状纹理。在非常缓慢的冷却过程中会出现大的光学活性畴，这归因于表面施加的非均质（扭曲）面内结构。在临界电场下，扭曲畴被抑制。本文提出了这种结构及其在电场中行为的简单模型。在进一步冷却时检测到的低温相归因于类似晶体的胶凝相。
• Potochromic liquid crystals
  申请人：Frigoli Michel

  公开号：US20050258396A1

  公开（公告）日：2005-11-24

  The invention relates to novel photochromic liquid crystal materials which may be used in various electro-optic devices including liquid crystal devices. The materials can be converted into another form on irradiation by light which may make it feasible for them to be addressed by light in electro-optic devices. The materials are based on 5-membered heterocycles.

  本发明涉及一种新型光致变色液晶材料，可用于各种电光器件，包括液晶器件。这些材料可以在受到光照射后转化为另一种形式，这使得它们可以被光地址化在电光器件中使用。这些材料基于5元杂环。
• Photochromic liquid crystals
  申请人：Chi Mei Optoelectronics Corporation

  公开号：US07416682B2

  公开（公告）日：2008-08-26

  The invention relates to novel photochromic liquid crystal materials which may be used in various electro-optic devices including liquid crystal devices. The materials can be converted into another form on irradiation by light which may make it feasible for them to be addressed by light in electro-optic devices. The materials are based on 5-membered heterocycles.

  本发明涉及一种新型的光致变色液晶材料，可用于各种电光设备，包括液晶设备。这些材料可以在光照下转化为另一种形式，这可能使它们能够被光在电光设备中寻址。这些材料基于5元杂环。
• Design of Siloxane Liquid Crystals Forming a De Vries SmA* Phase
  作者：G. Galli、M. Reihmann、A. Crudeli、E. Chiellini、Yu. Panarin、J. Vij、C. Blanc、V. Lorman、N. Olsson

  DOI：10.1080/15421400590958089

  日期：2005.6

  We designed and synthesized new SmA* liquid crystals with different molecular architectures based on the chiral mesogen MR11, which was unsubstituted, or attached at one end and at both ends of a trisiloxane segment in the monosubstituted MSi3-MR11 and disubstituted DSi3-MR11 siloxanes, respectively. We studied the critical divergence of the magnetic susceptibility by measurements of the induced tilt angle theta(ind) at the SmA*-SmC* transition. While all three SmA* liquid crystals presented a de Vries character, this was quite distinctive for DSi3-MR11 for which the critical exponent gamma = 1.87 was maximal. X-ray diffraction experiments confirmed that the SmA*-SmC* transition occurred with essentially no layer shrinkage.