4-dodecyloxy-4’-stilbazole | 300677-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-dodecyloxy-4’-stilbazole
• 英文别名: 4-dodecyloxy-4'-stilbazole；4-(4-dodecyloxystyryl)pyridine；4-[2-(4-Dodecoxyphenyl)ethenyl]pyridine
• CAS: 300677-65-0
• 化学式: C₂₅H₃₅NO
• 分子量: 365.559
• InChiKey: FRCDYVZDDBTMAN-UHFFFAOYSA-N

物化性质

• 沸点：
  501.3±19.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-dodecyloxy-4’-stilbazole 在 碘 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 2.0h， 以87%的产率得到
  参考文献：
  名称：

  Halogen-bonded liquid crystals of 4-alkoxystilbazoles with molecular iodine: a very short halogen bond and unusual mesophase stability

  摘要：

  含烷氧取代基的螺二扎嗪与分子碘形成的复合物是一种液晶，具有特别高的介相稳定性，其原因在于分子间存在的I⋯I接触。而尝试类似地制备含溴复合物时，却意外地形成了一个亲电取代产物。

  DOI：

  10.1039/c3cc41227j

文献信息

• Hydrogen-Bonded Complexes between 4-Alkoxystilbazoles and Fluorophenols: Solid-State Structures and Liquid Crystallinity
  作者：Joanna P.-W. Wong、Adrian C. Whitwood、Duncan W. Bruce

  DOI：10.1002/chem.201201906

  日期：2012.12.7

  of the new complexes showed liquid‐crystal properties and it was found that although complexes of butyloxystilbazole were all nematic, almost all of those with dodecyloxystilbazole showed a smectic A (SmA) phase. Complexes of octyloxystilbazole showed a mixture of both. Structure/property correlations showed that clearing points were independent of the pKa of the phenol. The most stable mesophases were

  通过将16种通式为C 6 F n H 5− n OH的氟酚与三种不同的烷氧基噻唑（丁氧基，辛氧基和十二烷氧基）混合，制备了48种新的氢键配合物。从辛基氧基噻唑的16种配合物中的10种获得了单晶X射线结构，发现根据该配合物和固态所显示的基序，大多数结构可以被收集为两组之一包装。因为只有一个结晶在P中在空间群中，可以进行有意义的比较，并且观察到六个结构在本质上极为接近，因此发现了明显的分子重叠。在此基础上，人们对在固态中发现的一些较弱的分子间接触的重要性表示怀疑。40种新的配合物表现出液晶性质，并且发现尽管丁氧基噻唑的复合物都是向列型的，但几乎所有十二烷基氧基噻唑的复合物都具有近晶A（SmA）相。辛氧基噻唑的复合物显示出两者的混合物。结构/性质的相关性表明清除点与p K a无关苯酚。当氟酚在2位上含有氟时，发现了最稳定的中间相，这可以通过分子内H⋅⋅⋅F氢键的形成形成一个六元环，将这两个组分连接成一个稳定分子来解释。
• Trimeric liquid crystals assembled using both hydrogen and halogen bonding
  作者：Carsten Präsang、H. Loc Nguyen、Peter N. Horton、Adrian C. Whitwood、Duncan W. Bruce

  DOI：10.1039/b811716k

  日期：——

  New liquid crystals are reported that are formed from non-mesomorphic components assembled using both halogen and hydrogen bonding.

  报道了一种由非介晶组分组成的新型液晶，这些组分通过卤素键和氢键结合而成。
• trans-Dichloro(stilbazole)(methyl n-alkyl sulfoxide)platinum(ii) complexes: the first examples of metallomesogens containing chiral centres directly bonded to the metal
  作者：Francesco Paolo Fanizzi、Vincenzo Alicino、Cosimo Cardellicchio、Paolo Tortorella、Jonathan P. Rourke

  DOI：10.1039/b000594k

  日期：——

  The first examples of enantiomerically pure metallomesogens containing the chiral centre directly bonded to the metal are reported; the chiral complexes show different phase behaviour to the racemic modifications.

  报道了第一批包含直接与金属键合的手性中心的对映纯金属原子的例子；这些手性复合物与外消旋的金属原子相比，表现出不同的相行为。
• Synthesis and photoisomerization of mesogenic 4-alkoxystyrylpyridines
  作者：O. A. Turanova、L. G. Gafiyatullin、O. I. Gnezdilov、A. N. Turanov

  DOI：10.1134/s1070363211050173

  日期：2011.5

  Introduction of long-chain alkoxy substituents into molecules of styrylpyridines as potential ligands for photosensitive metal complexes endows them with liquid crystalline properties over a wide temperature range. trans-cis Photoisomerization of 4-alkoxystyrylpyridines in solution was revealed by NMR and electronic absorption spectroscopy, and the kinetics of transformations of their molecular forms after irradiation were estimated. Photoinduced trans -> cis isomerization of 4-alkoxystyrylpyridines is characterized by a higher rate, and intramolecular cyclization of their cis isomers after irradiation is slower, as compared to unsubstituted analog.
• Synthesis and properties of (±)-trans-(η²-alkene)(4-alkyloxy-4′-stilbazole)dichloroplatinum: a remarkable family of low-melting metallomesogens
  作者：Jon P. Rourke、Francesco P. Fanizzi、Duncan W. Bruce、David A. Dunmur、Peter M. Maitlis

  DOI：10.1039/dt9920003009

  日期：——

  A novel series of low-melting metallomesogens (metal-containing liquid crystals) has been prepared and characterised. Reaction of Zeise's salt K[PtCl3 (eta2-CH2=CH2)] with the 4-n-alkyloxy-4'-stilbazole ligands (L = CnH2n+1OC6H4CH=CHC5H4N; n = 3-12) yielded trans- [PtCl2(eta2-CH2=CH2)L] 1, which react with alk-1-enes (CH2=CHCmH2m+1; m = 1-8, 10 or 12) to give trans-[PtCl2(CH2=CHCmH2m+1)L] 2. The complexes where (m + n) greater-than-or-equal-to ca. 8 are generally liquid crystalline (smectic A mesophases); those with shorter tails [(m + n) = 8 to ca. 13] show monotropic mesophases, while those with longer tails [(m + n) > ca. 1 3] show enantiotropic behaviour. The melting temperatures are lower than would be anticipated for metallomesogens of this size, reflecting the non-centrosymmetric molecular structures which make the crystal packing less easy. A 70:30 mixture of the complexes 2 (n = 12, m = 3; K --> S(A) at 61-degrees-C) and (n = 12, m = 6; K --> S(A) at 70-degrees-C) shows the transition into the mesophase, K --> S(A), at 45-degrees-C, an unusually low temperature. The mesophase to isotropic (S(A) --> 1) transition temperatures remain rather constant at 92 +/- 4-degrees-C for all compositions.