1-[2-(2-hydroxyethoxy)ethoxy]-5-[2-(2-methoxyethoxy)ethoxy]naphthalene | 189026-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[2-(2-hydroxyethoxy)ethoxy]-5-[2-(2-methoxyethoxy)ethoxy]naphthalene
• 英文别名: [(2-hydroxyethoxy)ethoxy]-5-[2-(2-methoxyethoxy)ethoxy]naphthalene；1-(2-(2-methoxyethoxyethoxy))-5-(2-(2-hydroxyethoxyethoxy))naphthalene；2-[2-[5-[2-(2-Methoxyethoxy)ethoxy]naphthalen-1-yl]oxyethoxy]ethanol
• CAS: 189026-89-9
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: MCJGLHXUFUGXOA-UHFFFAOYSA-N

物化性质

• 沸点：
  508.7±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-(2-hydroxyethoxy)ethoxy]-5-[2-(2-methoxyethoxy)ethoxy]naphthalene 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、1200.0 MPa 条件下， 反应 76.0h， 生成
  参考文献：
  名称：

  Simple Mechanical Molecular and Supramolecular Machines: Photochemical and Electrochemical Control of Switching Processes

  摘要：

  AbstractPhotochemical control of a self‐assembled supramolecular 1:1 pseudorotaxane (formed between a tetracationic cyclophane, namely the tetrachloride salt of cyclobis(paraquat‐p‐phenylene), and 1,5‐bis[2‐(2‐(2‐hydroxy)ethoxy)ethoxy]naphthalene) has been achieved in aqueous solution. The photochemical one‐electron reduction of the cyclophane to the radical trication weakens the noncovalent bonding interactions between the cyclophane and the naphthalene guest—π‐π interactions between the π‐electron‐rich and π‐electron‐poor aromatic systems, and hydrogen‐bonding interactions between the acidic α‐bipyridinium hydrogen atoms of the cyclophane and the polyether oxygen atoms of the naphthalene derivative—sufficiently to allow the guest to dethread from the cavity; the process can be monitored by the appearance of naphthalene fluorescence. The radical tricationic cyclophane can be oxidized back to the tetracation in the dark by allowing oxygen gas into the system. This reversible process is marked by the disappearance of naphthalene fluorescence as the molecule is recomplexed by the tetracationic cyclophane. This supramolecular system can be chemically modified such that the π‐electron‐rich unit, either a naphthalene derivative or a hydroquinone ring, and the tetracationic cyclophane are covalently linked. We have demonstrated that the π‐electron‐rich residue in this system is totally “self‐complexed” by the cyclophane to which it is covalently attached. Additionally, the self‐complexation can be switched “off” and “on” by electrochemical two‐electron reductions and oxidations, respectively, of the tetracationic cyclophane component. Thus, we have achieved the construction of two switches at the nanoscale level, one driven by photons and the other by electrons.

  DOI：

  10.1002/chem.19970030123
• 作为产物：
  描述：

  1,5-二羟基萘 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 1-[2-(2-hydroxyethoxy)ethoxy]-5-[2-(2-methoxyethoxy)ethoxy]naphthalene
  参考文献：
  名称：

  Simple Mechanical Molecular and Supramolecular Machines: Photochemical and Electrochemical Control of Switching Processes

  摘要：

  AbstractPhotochemical control of a self‐assembled supramolecular 1:1 pseudorotaxane (formed between a tetracationic cyclophane, namely the tetrachloride salt of cyclobis(paraquat‐p‐phenylene), and 1,5‐bis[2‐(2‐(2‐hydroxy)ethoxy)ethoxy]naphthalene) has been achieved in aqueous solution. The photochemical one‐electron reduction of the cyclophane to the radical trication weakens the noncovalent bonding interactions between the cyclophane and the naphthalene guest—π‐π interactions between the π‐electron‐rich and π‐electron‐poor aromatic systems, and hydrogen‐bonding interactions between the acidic α‐bipyridinium hydrogen atoms of the cyclophane and the polyether oxygen atoms of the naphthalene derivative—sufficiently to allow the guest to dethread from the cavity; the process can be monitored by the appearance of naphthalene fluorescence. The radical tricationic cyclophane can be oxidized back to the tetracation in the dark by allowing oxygen gas into the system. This reversible process is marked by the disappearance of naphthalene fluorescence as the molecule is recomplexed by the tetracationic cyclophane. This supramolecular system can be chemically modified such that the π‐electron‐rich unit, either a naphthalene derivative or a hydroquinone ring, and the tetracationic cyclophane are covalently linked. We have demonstrated that the π‐electron‐rich residue in this system is totally “self‐complexed” by the cyclophane to which it is covalently attached. Additionally, the self‐complexation can be switched “off” and “on” by electrochemical two‐electron reductions and oxidations, respectively, of the tetracationic cyclophane component. Thus, we have achieved the construction of two switches at the nanoscale level, one driven by photons and the other by electrons.

  DOI：

  10.1002/chem.19970030123

文献信息

• A triple carboxylic acid-functionalized RAFT agent platform for the elaboration of well-defined telechelic 3-arm star PDMAc
  作者：K. Belal、S. Poitras-Jolicoeur、J. Lyskawa、G. Pembouong、G. Cooke、P. Woisel、F. Stoffelbach

  DOI：10.1039/c5cc09684g

  日期：——

  This communication describes the synthesis of a triple acid-functionalized RAFT agent and its use to prepare well-defined 3-arm star polymers ofN,N-dimethylacrylamide (DMAc).

  这份通讯描述了三羧酸官能化RAFT试剂的合成及其用于制备明确定义的三臂星形聚合物N,N-二甲基丙烯酰胺（DMAc）的过程。
• Model systems for flavoenzyme activity: intramolecular self-assembly of a flavin derivative via hydrogen bonding and aromatic interactions
  作者：Stuart T. Caldwell、Graeme Cooke、Shanika G. Hewage、Suhil Mabruk、Gouher Rabani、Vincent Rotello、Brian O. Smith、Chandramouleeswaran Subramani、Patrice Woisel

  DOI：10.1039/b809762c

  日期：——

  We have synthesised a flavin derivative incorporating functionalities that promote intramolecular self-assembly via hydrogen bonding and aromatic interactions.

  我们已经合成了一种结合了功能的黄素衍生物，该功能通过氢键和芳族相互作用促进分子内自组装。
• The tuneable complexation of gold nanoparticles
  作者：Graeme Cooke、James F. Garety、Shanika Gunatilaka Hewage、Gouher Rabani、Vincent M. Rotello、Patrice Woisel

  DOI：10.1039/b608543a

  日期：——

  Mixed monolayer protected gold nanoparticles have been fabricated incorporating 1,5-dialkyloxynaphthalene moieties that are capable of forming complexes with the tetracationic cyclophane cyclobis(paraquat-p-phenylene); electrochemical reduction of the cyclophane or the addition of tetrathiafulvalene results in disassembly of the complexes.

  混合单层保护金纳米粒子中含有 1,5-二烷氧基萘分子，能够与四呲阳离子环烷环双（百草枯-对苯烯）形成络合物；环烷的电化学还原或加入四硫代富勒烯会导致络合物解体。
• LCST: a powerful tool to control complexation between a dialkoxynaphthalene-functionalised poly(N-isopropylacrylamide) and CBPQT4+ in water
  作者：Julien Bigot、Marc Bria、Stuart T. Caldwell、Frédéric Cazaux、Alan Cooper、Bernadette Charleux、Graeme Cooke、Brian Fitzpatrick、David Fournier、Joel Lyskawa、Margaret Nutley、François Stoffelbach、Patrice Woisel

  DOI：10.1039/b910856d

  日期：——

  We describe the application of the LCST of a naphthalene-functionalised polyNIPAM derivative as a convenient, tuneable and reversible method to disrupt complex formation with CBPQT4+ in water.

  我们描述了萘功能化聚 NIPAM 衍生物 LCST 的应用，它是一种方便、可调且可逆的方法，用于破坏 CBPQT4+ 在水中形成的复合物。
• Programmable Polymer‐Based Supramolecular Temperature Sensor with a Memory Function
  作者：Léna Sambe、Victor R. de La Rosa、Khaled Belal、François Stoffelbach、Joel Lyskawa、François Delattre、Marc Bria、Graeme Cooke、Richard Hoogenboom、Patrice Woisel

  DOI：10.1002/anie.201402108

  日期：2014.5.12

  A new class of polymeric thermometers with a memory function is reported that is based on the supramolecular host–guest interactions of poly(N‐isopropylacrylamide) (PNIPAM) with side‐chain naphthalene guest moieties and the tetracationic macrocycle cyclobis(paraquat‐p‐phenylene) (CBPQT4+) as the host. This supramolecular thermometer exhibits a memory function for the thermal history of the solution

  据报道，一类具有记忆功能的新型聚合物温度计是基于聚（N-异丙基丙烯酰胺）（PNIPAM）与侧链萘客体部分和四阳离子大环环双（百草枯-对-亚苯基）的超分子主客体相互作用）（CBPQT 4+）作为主机。该超分子温度计对溶液的热历史表现出记忆功能，这是由于热响应性LCST相变的大滞后（LCST =较低的临界溶液温度）引起的。该磁滞是基于由PNIPAM–CBPQT 4+组成的亚稳态可溶状态形成的。主客复合体。当加热到转变温度以上时，聚合物崩溃，主体与客体之间的相互作用被破坏，使聚合物更具疏水性，而在水中的溶解性降低。除了提供对超分子组件的动力学控制的基本见解之外，开发的具有记忆功能的温度计可能会在涉及物理和生物科学的应用中找到用处。