2,8,14,20-tetrakis-(3-iodopropyl)-4,6,10,12,16,18,22,24-octakis(ethoxycarbonylmethoxy)calix[4]arene | 212915-83-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,8,14,20-tetrakis-(3-iodopropyl)-4,6,10,12,16,18,22,24-octakis(ethoxycarbonylmethoxy)calix[4]arene
• 英文别名: Ethyl 2-[[6,10,12,16,18,22,24-heptakis(2-ethoxy-2-oxoethoxy)-2,8,14,20-tetrakis(3-iodopropyl)-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]oxy]acetate
• CAS: 212915-83-8
• 化学式: C₇₂H₉₂I₄O₂₄
• 分子量: 1849.13
• InChiKey: YXSBKCGASKSMNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  100
• 可旋转键数：
  52
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  284
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  p-hydroxy-p'-octyl-azobenzene 、 2,8,14,20-tetrakis-(3-iodopropyl)-4,6,10,12,16,18,22,24-octakis(ethoxycarbonylmethoxy)calix[4]arene 生成
  参考文献：
  名称：

  Self-Assembled Monolayers Derived from Calix[4]resorcinarenes Exhibiting Excellent Desorption-Resistance and Their Applicability to Surface Energy Photocontrol

  摘要：

  自我组装的单层显示出优良的吸收阻力,是通过通过多点吸收在氨基硅基基基基上吸收O-carboxymethylated(4)resorcinarenes的冠式合成剂。

  DOI：

  10.1246/cl.1999.349
• 作为产物：
  描述：

  在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 12.0h， 以90%的产率得到2,8,14,20-tetrakis-(3-iodopropyl)-4,6,10,12,16,18,22,24-octakis(ethoxycarbonylmethoxy)calix[4]arene
  参考文献：
  名称：

  Monolayers of Calix[4]resorcinarenes with Azobenzene Residues Exhibiting Efficient Photoisomerizability

  摘要：

  从 O-octacarboxymethoxylated calix[4]resorcinarenes 的冠构象下缘拴系的偶氮苯分别在水面上的致密单层、LB 薄膜和表面吸附单层中显示出高效的 E-to-Z 光异构性。

  DOI：

  10.1246/cl.1998.165

文献信息

• Enhancement of desorption resistance of adsorbed monolayers of calix[4]resorcinarenes bearing cinnamoyl residues by photodimerization
  作者：Yuko Hayashi、Shintaro Suzuki、Kunihiro Ichimura

  DOI：10.1039/b100034i

  日期：——

  The crown conformer of a calix[4]resorcinarene (CRA) possessing eight carboxymethylated units at the lower rim and four cinnamoyl residues at the upper rim was prepared to fabricate photofunctional monomolecular layers. The CRA derivative was adsorbed on a fused silica plate from a THF solution to form a monomolecular layer through hydrogen bonds. The monolayer exhibited photocycloaddition, together with photoisomerization, upon UV irradiation. Whereas the desorption of the macrocyclic compound from the plate occurred partially in polar solvents including ethanol, UV irradiation exhibited a suppressive effect on the desorption, suggesting that the number of hydrogen bonds between the molecules and a silica surface per molecule are much enhanced by intermolecular photodimerization of the cinnamoyl residues leading to an increment of the molecular weight of the adsorbate. The monolayer of the CRA on a silica plate exhibited the ability to transform the alignment of a nematic liquid crystal upon UV irradiation from homeotropic (perpendicular) to planar (parallel) orientation. The photoalignment of the liquid crystal was stabilized toward heat treatment possibly owing to the photodimerization of cinnamoyl units.

  为了制造光功能单分子层，我们制备了钙[4]间苯二酚（CRA）的冠构象，其下缘具有八个羧甲基单元，上缘具有四个肉桂酰残基。CRA 衍生物从四氢呋喃溶液中吸附到熔融石英板上，通过氢键形成单分子层。该单分子层在紫外线照射下表现出光环加成和光异构化。在极性溶剂（包括乙醇）中，大环化合物会从平板上部分解吸，而紫外线照射对解吸有抑制作用，这表明由于肉桂酰残基的分子间光二聚化导致吸附剂分子量增加，分子与二氧化硅表面之间的氢键数量大大增加。二氧化硅板上的单层 CRA 在紫外线照射下能够将向列液晶的排列从各向同性（垂直）方向转变为平面（平行）方向。可能是由于肉桂酰单位的光二聚化作用，液晶的光排列在热处理后趋于稳定。