2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanol | 145839-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanol
• 英文别名: 2-[2-[2-[4-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]phenoxy]ethoxy]ethoxy]ethanol
• CAS: 145839-41-4
• 化学式: C₄₃H₄₈O₈
• 分子量: 692.849
• InChiKey: BYXVLUGCLKSXBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  51.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

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>ethanol 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 生成 2-methyl-5-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]-3-[2-[2-[2-[2-[4-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]phenoxy]ethoxy]ethoxy]ethoxy]ethyl]-1H-indole
  参考文献：
  名称：

  Toward Controllable Molecular Shuttles

  摘要：

  AbstractA number of nanometer‐scale molecular assemblies, based on rotaxane‐type structures, have been synthesized by means of a template‐directed strategy from simple building blocks that, on account of the molecular recognition arising from the noncovalent interactions between them, are able to self‐assemble into potential molecular abacuses. In all the cases investigated, the π‐electron‐deficient tetracationic cyclophane cyclobis(paraquat‐p‐phenylene) is constrained mechanically around a dumbbell‐shaped component consisting of a linear polyether chain intercepted by at least two, if not three, π‐electron‐rich units and terminated at each end by blocking groups or stoppers. The development of an approach toward constructing these molecular abacuses, in which the tetracationic cyclophane is able to shuttle back and forth with respect to the dumbbell‐shaped component, begins with the self‐assembly of a [2]rotaxane consisting of two hydroquinone rings symmetrically positioned within a polyether chain terminated by triisopropylsilyl ether blocking groups. In this first so‐called molecular shuttle, the tetracationic cyclophane oscillates in a degenerate fashion between the two π‐electron‐rich hydroquinone rings. Replacement of one of the hydroquinone rings—or the insertion of another π‐electron‐rich ring system between the two hydroquinine rings—introduces the possibility of translational isomerism, a phenomenon that arises because of the different relative positions and populations of the tetracationic cyclophane with respect to the π‐donor sites on the dumbbell‐shaped component. In two subsequent [2]rotaxanes, one of the hydroquinone rings in the dumbbell‐shaped component is replaced, first by a p‐xylyl and then by an indole unit. Finally, a tetrathiafulvalene (TTF) unit is positioned between two hydroquinone rings in the dumbbell‐shaped component. Spectroscopic and electrochemical investigations carried out on these first‐generation molecular shuttles show that they could be developed as molecular switches.

  DOI：

  10.1002/chem.19970030719
• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 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 259.0h， 生成 2-<2-<2-<4-<2-<2-<2-(4-triphenylmethylphenoxy)ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethanol
  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

• 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.