2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanoltosylate | 189118-56-7

• 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: 2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanoltosylate
• 英文别名: 2-[2-[2-[4-[2-[2-[2-(4-Tritylphenoxy)ethoxy]ethoxy]ethoxy]phenoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 189118-56-7
• 化学式: C₅₀H₅₄O₁₀S
• 分子量: 847.039
• InChiKey: UVZJRBNVMLHGJB-UHFFFAOYSA-N

物化性质

• 沸点：
  901.2±65.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  61
• 可旋转键数：
  27
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanoltosylate 、 5-Bromo-2-fluorotoluene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以15%的产率得到trans-4,4'-bis-<2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethoxy>azobenzene
  参考文献：
  名称：

  Photoactive Azobenzene-Containing Supramolecular Complexes and Related Interlocked Molecular Compounds

  摘要：

  Two acyclic and three macrocyclic polyethers, three [2]catenanes, and one [2]rotaxane, each containing one 4,4'-azobiphenoxy unit, have been synthesized. In solution, the azobenzene-based acyclic polyethers are bound by cyclobis(paraquat-p-phenylene)-a tetracationic cyclophane-in their trans forms only. On irradiation (lambda = 360 nm) of an equimolar solution of the tetracationic cyclophane host and one of the guests containing a trans-4,4'-azobiphenoxy unit, the trans double bond isomerizes to its cis form and the supramolecular complex dissociates into its molecular components. The trans isomer of the guest and, as a result, the complex are reformed, either by irradiation (lambda = 440 nm) or by warming the solution in the dark. Variable temperature H-1 NMR spectroscopic investigations of the [2]catenanes and the [2]rotaxane revealed that, in all cases, the 4,4'-azobiphenoxy unit resides preferentially alongside the cavities of their tetracationic cyclophane components, which are occupied either by a 1,4-dioxybenzene or by a 1,5-dioxynaphthalene unit. In the acyclic and macrocyclic polyethers containing 1,4-dioxybenzene or 1,5-dioxynaphthalene chromophoric groups and a 4,4'-azobiphenoxy moiety, the fluorescence of the former units is quenched by the latter. Fluorescence quenching is accompanied by photosensitization of the isomerization. The rate of the energy-transfer process is different for trans and cis isomers. In the [2]rotaxane and the [2]catenanes, the photoisomerization is quenched to an extent that depends on the specific structure of the compound. Only in one of the three [2]catenanes and in the [2]rotaxane was an efficient photoisomerization (lambda=360 nm) from the trans to the cis isomer of the 4,4'-azobiphenoxy unit observed. Single crystal X-ray structural analysis of one of the [2]catenanes showed that, in the solid state, the 4,4'-azobiphenoxy unit in the macrocyclic polyether component also resides exclusively alongside. The cavity of the tetracationic cyclophane component of the [2]catenane is filled by a 1,5-dioxynaphthalene unit, and infinite donor-acceptor stacks between adjacent [2]catenanes are formed in the crystal. These supramolecular complexes and their mechanically interlocked molecular counterparts can be regarded as potential photoactive nanoscale devices.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<860::aid-chem860>3.0.co;2-k
• 作为产物：
  描述：

  4-苄氧基苯酚 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 261.0h， 生成 2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanoltosylate
  参考文献：
  名称：

  两站和三站[2]轮烷的平移异构现象。

  摘要：

  描述了三种[2]轮烷的模板指导的合成。它们都具有哑铃成分，氢醌和间苯二酚环均插入四芳基甲烷塞终止的聚醚链中，在关键的自组装过程中被四阳离子环烷，环双（百草枯-对苯撑）及其两个pi-环包围。电子不足的联吡啶单元。通过低温（1）H NMR光谱已经证明，π电子缺陷的四阳离子环烷具有非常高的优先级，以位于这些分子穿梭中的氢醌环周围。

  DOI：

  10.1021/jo9612584

文献信息

• Translational Isomerism in Some Two- and Three-Station [2]Rotaxanes
  作者：David B. Amabilino、Peter R. Ashton、Sue E. Boyd、Marcos Gómez-López、Wayne Hayes、J. Fraser Stoddart

  DOI：10.1021/jo9612584

  日期：1997.5.1

  The template-directed syntheses of three [2]rotaxanes are described. They all have dumbbell components, with both hydroquinone and resorcinol rings inserted into polyether chains terminated by tetraarylmethane stoppers, that become encircled during the key self-assembly processes by the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), with its two pi-electron deficient bipyridinium units.

  描述了三种[2]轮烷的模板指导的合成。它们都具有哑铃成分，氢醌和间苯二酚环均插入四芳基甲烷塞终止的聚醚链中，在关键的自组装过程中被四阳离子环烷，环双（百草枯-对苯撑）及其两个pi-环包围。电子不足的联吡啶单元。通过低温（1）H NMR光谱已经证明，π电子缺陷的四阳离子环烷具有非常高的优先级，以位于这些分子穿梭中的氢醌环周围。
• Photoactive Azobenzene-Containing Supramolecular Complexes and Related Interlocked Molecular Compounds
  作者：Masumi Asakawa、Peter R. Ashton、Vincenzo Balzani、Christopher L. Brown、Alberto Credi、Owen A. Matthews、Simon P. Newton、Françisco M. Raymo、Andrew N. Shipway、Neil Spencer、Andrew Quick、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/(sici)1521-3765(19990301)5:3<860::aid-chem860>3.0.co;2-k

  日期：1999.3.1

  Two acyclic and three macrocyclic polyethers, three [2]catenanes, and one [2]rotaxane, each containing one 4,4'-azobiphenoxy unit, have been synthesized. In solution, the azobenzene-based acyclic polyethers are bound by cyclobis(paraquat-p-phenylene)-a tetracationic cyclophane-in their trans forms only. On irradiation (lambda = 360 nm) of an equimolar solution of the tetracationic cyclophane host and one of the guests containing a trans-4,4'-azobiphenoxy unit, the trans double bond isomerizes to its cis form and the supramolecular complex dissociates into its molecular components. The trans isomer of the guest and, as a result, the complex are reformed, either by irradiation (lambda = 440 nm) or by warming the solution in the dark. Variable temperature H-1 NMR spectroscopic investigations of the [2]catenanes and the [2]rotaxane revealed that, in all cases, the 4,4'-azobiphenoxy unit resides preferentially alongside the cavities of their tetracationic cyclophane components, which are occupied either by a 1,4-dioxybenzene or by a 1,5-dioxynaphthalene unit. In the acyclic and macrocyclic polyethers containing 1,4-dioxybenzene or 1,5-dioxynaphthalene chromophoric groups and a 4,4'-azobiphenoxy moiety, the fluorescence of the former units is quenched by the latter. Fluorescence quenching is accompanied by photosensitization of the isomerization. The rate of the energy-transfer process is different for trans and cis isomers. In the [2]rotaxane and the [2]catenanes, the photoisomerization is quenched to an extent that depends on the specific structure of the compound. Only in one of the three [2]catenanes and in the [2]rotaxane was an efficient photoisomerization (lambda=360 nm) from the trans to the cis isomer of the 4,4'-azobiphenoxy unit observed. Single crystal X-ray structural analysis of one of the [2]catenanes showed that, in the solid state, the 4,4'-azobiphenoxy unit in the macrocyclic polyether component also resides exclusively alongside. The cavity of the tetracationic cyclophane component of the [2]catenane is filled by a 1,5-dioxynaphthalene unit, and infinite donor-acceptor stacks between adjacent [2]catenanes are formed in the crystal. These supramolecular complexes and their mechanically interlocked molecular counterparts can be regarded as potential photoactive nanoscale devices.