4'-(10-undecen-1-yloxy)-1,1'-biphenyl-4-carboxylic acid | 151419-76-0

• 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-undecen-1-yloxy)-1,1'-biphenyl-4-carboxylic acid
• 英文别名: 4'-undec-10-enyloxy-biphenyl-4-carboxylic acid；4'-(10-undecen-1-yloxy)-4-biphenylcarboxylic acid；4-(10-Undecen-1-yloxy)biphenyl-4'-carboxylic acid；4-(4-undec-10-enoxyphenyl)benzoic acid
• CAS: 151419-76-0
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: LKPLCWGQFFBLAV-UHFFFAOYSA-N

物化性质

• 熔点：
  163 °C(Solvent: Methanol)
• 沸点：
  515.2±43.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-(10-undecen-1-yloxy)-1,1'-biphenyl-4-carboxylic acid 在 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 4'-(11-acryloyloxy-undecyloxy)-biphenyl-4-carboxylic acid 4-(9-acryloyloxy-1(R)-methyl-nonyloxy)-phenyl ester
  参考文献：
  名称：

  一种用于二阶非线性光学的新型交联聚合物的制备

  摘要：

  制备了一种具有显着二阶非线性光学特性的新型交联热电聚合物。具有多个选择性转化的多步合成，包括使用高度对映选择性南极念珠菌脂肪酶 B 的动力学拆分（酯交换），产生单体 4''-{(R)-(-)-2-[(10-丙烯酰氧基)癸基]氧基}-3-硝基苯基4-{4'-[(11-丙烯酰氧基)十一烷氧基]苯基}苯甲酸酯A2c，显示出具有大自发极化(175 nC/cm2)的铁电手性近晶C相。单体被极化并随后通过原位光聚合在表面稳定的铁电液晶状态下交联。交联的热电聚合物表现出 15-35 pm/V 的电光系数 (r22 - r12)。

  DOI：

  10.1021/ja961309e
• 作为产物：
  描述：

  1-(4-甲氧基-联苯-4-基)-乙酮 在 氢氧化钾 、 氢溴酸 、 溴 、 溶剂黄146 、 potassium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 27.0h， 生成 4'-(10-undecen-1-yloxy)-1,1'-biphenyl-4-carboxylic acid
  参考文献：
  名称：

  Effects of nitro substituents on the properties of a ferroelectric liquid crystalline side chain polysiloxane

  摘要：

  本文描述了具有侧链硝基取代基和介晶核心的手性液晶侧链聚硅氧烷的合成。研究并比较了取代基及其位置对相行为和电光性质的影响。侧链前体及液晶聚合物的相行为受到侧向硝基的强烈影响。讨论了在层状A相和C*相中各取代基位置的性质。一种侧链前体表现出约700 nC cm–2的非常大自发极化。

  DOI：

  10.1039/a704918h

文献信息

• Gas Chromatographic Separation of Structural Isomers on Cholesteric Liquid Crystal Stationary Phase Materials
  作者：Yi-Wen Lee、Chih-Hung Lin

  DOI：10.14233/ajchem.2013.13927

  日期：——

  A new series of liquid crystalline polysiloxanes with a very wide range of mesomorphic temperatures had been prepared. They contained 4-cholesteryl-(10-undecen-1-yloxy)biphenyl- 4¢-carboxylate mesogenic and 4-biphenyl-4¢-allyloxybenzoate mesogenic side groups displaying an enantiotropic cholesteric phases. The mesomorphic polysiloxane specimen with the widest temperature range was used as the stationary phase in a gas chromatography capillary column and it showed high column efficiency and made great promise for the separation of different structure isomer compounds.

  制备了一系列具有非常宽泛液晶温度的液态晶体聚硅氧烷。这些聚硅氧烷包含了4-胆固醇基-(10-十一碳烯-1-氧基)联苯-4¢-羧酸酯液晶侧链和4-联苯-4¢-烯丙氧基苯甲酸酯液晶侧链，呈现出对映异构胆甾相。具有最宽温度范围的液晶聚硅氧烷样品被用作气相色谱毛细管柱的固定相，显示出高柱效能，并有望用于不同结构异构化合物的分离。
• Ester type banana-shaped liquid crystalline monomers: synthesis and physical properties
  作者：Katalin Fodor-Csorba、Anikó Vajda、Antal Jákli、Christian Slugovc、Gregor Trimmel、Dietrich Demus、Eszter Gács-Baitz、Sándor Holly、Giancarlo Galli

  DOI：10.1039/b400246f

  日期：——

  New ester-type banana (bent-shaped) monomers, 1,3-phenylene bis[4′-(alken-1-yloxy)-biphenyl-4-carboxylate]s Ia–Vb, with different substituent(s) on the central phenyl ring (H, CH3, Cl or NO2) and alkenyl tails in the side arms (decenyl or undecenyl) were prepared. The analogues IIIa–IVb with 4-chloro- or 4,6-dichloro-substituents exhibited a nematic phase, while Va,Vb with 2-nitro-substituent showed a B7 phase at relatively low temperature. All the compounds were stable, no degradation or polymerization was observed under applied electric fields or heat treatments. Electro-hydrodynamic instabilities were observed in the nematic phase of each sample. In the B7 phase of Vb there was an electro-optical switching in the range 112–114.5 °C with a switching time of about 150 µs at 20 V µm−1 field. At lower temperatures no electro-optical switching occurred, but a ferroelectric-type spontaneous polarization of 22 nC cm−2 could be detected. The bend angle was calculated by the semiempirical CAChe/MOPAC/PM5 method.

  新型的酯类香蕉型（弯曲形状）单体，1,3-亚苯基双[4'-(烯-1-氧基)-联苯-4-羧酸酯] Ia–Vb，具有不同取代基在中心苯环上（H、CH3、Cl 或 NO2）和侧臂上的烯基尾（癸烯基或十一烯基），已被制备。具有4-氯或4,6-二氯取代基的类似物 IIIa–IVb 显示出向列相，而具有2-硝基取代基的 Va,Vb 在相对较低的温度下显示出B7相。所有化合物都稳定，未观察到在应用的电场或热处理下发生降解或聚合。在每个样品的向列相中观察到电-流体动力学不稳定性。在Vb的B7相中，在112–114.5 °C范围内存在电光开关，在20 V µm−1场的开关时间约为150 µs。在较低温度下没有电光开关发生，但可以检测到铁电型自发极化22 nC cm−2。通过半经验的CAChe/MOPAC/PM5方法计算弯曲角度。
• Synthesis and mesomorphic properties of new organosiloxane chiral calamitic liquid crystals
  作者：Hale Ocak、Burcu Karaağaç、Huriye Akdaş-Kılıç、Olivier Jeannin、Franck Camerel、Belkız Bilgin Eran

  DOI：10.1016/j.molliq.2021.118077

  日期：2022.2

  chiral moiety and siloxane segments within the same structure on liquid crystalline properties. The chiral calamitic compound and derivatives with a siloxane end-group or a siloxane spacer have been characterized using classical spectroscopic methods (1H-NMR, 13C-NMR, 29Si-NMR and MS) and elemental analysis (EA). The liquid crystalline properties of all new compounds were investigated by differential scanning

  合成了一种新的手性棒状化合物，由苯基核通过酯连接体连接到一侧带有手性 ( S )-2-甲基丁氧基的苯甲酸酯和另一侧带有十一碳烯氧基链的羧酸联苯酯。此外，通过氢化硅烷化反应获得了硅氧烷取代的衍生物和具有由二硅氧烷间隔基连接的这两个相同手性棒状体的二聚体，以研究将手性部分和硅氧烷链段结合在同一结构内对液晶性能的影响。具有硅氧烷端基或硅氧烷间隔基的手性棒状化合物和衍生物已使用经典光谱方法 ( 1 H-NMR, 13 C-NMR, 29Si-NMR 和 MS) 和元素分析 (EA)。通过差示扫描量热法、光学偏光显微镜、X 射线散射和电光方法研究了所有新化合物的液晶性质。随着硅氧烷端基的引入，具有对映手性向列相（N*）和手性倾斜近晶相（SmC*）的端乙烯基棒状化合物，强烈促进了稳定近晶相的出现。以类似的方式，除了存在 N* 中间相之外，具有通过二硅氧烷间隔基连接的两个相同棒状介晶的二聚体还表现出更宽
• A new series of liquid crystalline dimers with exceptionally high apparent tilt
  作者：Nils Olsson、Martin Schröder、Siegmar Diele、Gunnar Andersson、Ingolf Dahl、Bertil Helgee、Lachezar Komitov

  DOI：10.1039/b615541c

  日期：——

  A new series of dimeric chiral antiferroelectric materials using a trisiloxane as the central connecting linker and having fluorinated tails has been synthesized together with their corresponding monomers. Spacer lengths of 3–6 and 11 methylene groups were used. As a comparison to see the effect of the siloxane length on the phase behaviour, one dimer with a tetrasiloxane core was also synthesized. Monomers with 3–6 carbons in the spacer showed just orthogonal smectic phases and only the long 11 carbon spacer 7F4PPB11 showed tilted phases in a very similar way to what was found in the unfluorinated monomers previously studied. All trisiloxanes showed a high temperature antiferroelectric phase and those with a spacer length of 4 or more carbons also showed one or two columnar antiferroelectric phases when decreasing the temperature. The spontaneous polarisation Ps was high, especially in the columnar phases where it ranged from 800–1200 nC cm–2 and upward. The apparent tilt angles were exceptionally high, above 45 degrees for all materials studied. In accordance with the trend described previously, the tetrasiloxane containing dimer showed a ferroelectric phase at high temperature. But in this case the columnar phase was found to be antiferroelectric. Hence, the general idea that trisiloxane cores promote antiferroelectricity and tetrasiloxanes promote the ferroelectric phase is still correct also for these materials in the SmC* phase, but not for the columnar phase. It can also be noted that the phase separation between siloxane, fluorinated tail and mesogenic parts of the molecules was so high that the material became columnar on lowering the temperature.

  我们合成了一系列新的二聚手性反铁电材料，这些材料使用三硅氧烷作为中心连接物，并具有氟化尾部及其相应的单体。使用的间隔长度为 3-6 和 11 个亚甲基。为了比较硅氧烷长度对相行为的影响，还合成了一种以四硅氧烷为核心的二聚体。间隔碳数为 3-6 个的单体只显示出正交的平滑相，只有 11 个碳的长间隔碳 7F4PPB11 显示出倾斜相，与之前研究的无氟单体非常相似。所有三硅氧烷都显示出高温反铁电相，而那些具有 4 个或更多碳间隔长度的三硅氧烷在降低温度时也显示出一个或两个柱状反铁电相。自发极化 Ps 很高，尤其是在柱状相中，其范围在 800-1200 nC cm-2 及以上。所有研究材料的视倾角都非常高，超过 45 度。与之前描述的趋势一致，含有四硅氧烷的二聚体在高温下呈现铁电相。但在这种情况下，柱状相被发现是反铁电相。因此，三硅氧烷核心促进反铁电性，而四硅氧烷促进铁电相的一般观点对于这些处于 SmC* 相的材料来说仍然是正确的，但对于柱状相来说并不正确。我们还注意到，分子中硅氧烷、氟化尾部和介电部分之间的相分离程度非常高，以至于在降低温度时材料会变成柱状。
• First liquid single crystal elastomer containing lactic acid derivative as chiral co-monomer: Synthesis and properties
  作者：Alexej Bubnov、Valentina Domenici、Věra Hamplová、Miroslav Kašpar、Bostjan Zalar

  DOI：10.1016/j.polymer.2011.07.046

  日期：2011.9

  For the first time new type of liquid single crystal elastomers forming the chiral smectic A* (SmA*) phase has been prepared using chiral lactic acid derivative as a co-monomer. The synthesis and the basic characterization of the ferroelectric liquid crystalline co-monomer based on differential scanning calorimetry and small/wide-angle X-ray scattering are reported and discussed. The monomer possesses

  首次使用手性乳酸衍生物作为共聚单体制备了形成手性近晶A *（SmA *）相的新型液晶单晶弹性体。报道和讨论了基于差示扫描量热法和小/广角X射线散射的铁电液晶共聚单体的合成和基本表征。单体在较宽的温度范围内具有顺电SmA *和铁电SmC *相。还报道了新的近晶液晶弹性体的制备以及它们的介晶和结构性质的表征。新型弹性体具有正交顺电SmA * 50 K的宽温度范围内的相位。