1,4-bis[2-(2-hydroxyethoxy)ethoxy]benzene bis(4-methylbenzenesulfonate) | 135974-61-7

• 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: 1,4-bis[2-(2-hydroxyethoxy)ethoxy]benzene bis(4-methylbenzenesulfonate)
• 英文别名: 1,4-bis[2-(2-hydroxyethoxy)ethoxy]benzene bis (4-methylbenzenesulfonate)；Benzene, 1,4-bis[2-[2-[(4-methylphenyl)sulfonyloxy]ethoxy]ethoxy]-；2-[2-[4-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]phenoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 135974-61-7
• 化学式: C₂₈H₃₄O₁₀S₂
• 分子量: 594.704
• InChiKey: IBNNYBXUYYBKHX-UHFFFAOYSA-N

物化性质

• 沸点：
  729.7±60.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4-bis[2-(2-hydroxyethoxy)ethoxy]benzene bis(4-methylbenzenesulfonate) 在 邻四氯苯醌 、 potassium carbonate 、 三氯乙酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 35.5h， 生成 2,8,12,18-tetraethyl-3,7,13,17-tetramethyl-5,15-<1,4-phenylenebis<<<<(oxyethylene)oxy>ethylene>oxy>phenyl>>porphyrin
  参考文献：
  名称：

  Self-Assembling Porphyrin [2]-Catenanes

  摘要：

  Using the concepts of self-assembly developed for the construction of topologically complex molecules such as [2]-catenanes and rotaxanes, the syntheses of several prophyrin-catenanes are described. The successful insertion of the porphyrin subunit into [2]-catenanes has resulted from the adaptation of previously devised template-directed syntheses based primarily on pi-pi interactions and C-H...O and C-H...pi and hydrogen bonding. Several hydroquinol containing ether chains were successfully synthesized and subsequently strapped across a porphyrin ring; the X-ray crystal structures of two such molecules which vary in the length of the ether chain are reported. These strapped porphyrins were found to complex paraquat with a parallel orientation of the hydroquinol, paraquat, and porphyrin rings. The complexation of paraquat (K-a 1955 and 1640 M(-1), Delta G degrees = -4.5 and -4.4 kcal mol(-1) for 9 and 11, respectively) by these strapped porphyrins led to their subsequent inclusion, using template-directed self-assembly, into structures which represent the first examples of porphyrin-containing [2]-catenanes. The catenanes were subsequently characterized by FAB-MS and thoroughly examined using dynamic H-1 NMR. In the case of the hydroquinol-containing catenanes, a dynamic process was observed in solution in which the bipyridinium subunits of the tetracation were exchanged between ''inside'' and ''outside'' environments (rotation around the hydroquinol ring axis). The diethylene glycol containing catenanes 14 and 15 were observed to maintain an orientation of the tetracation in which the bipyridinium subunits are parallel to the porphyrin ring. The length of the ether strap in these catenanes influenced the rotation rates of the tetracation macrocycles (50 and 80 times per second for 14 and 15 and 2500 and 1500 times per second for 16 and 17, respectively) at ambient temperature. However, in air the catenanes, the overall orientation of the tetracation,with bipyridinium and porphyrin rings coparallel, is retained in solution. As an extension of the original concepts, an analogous strapped porphyrin containing a naphthoquinol moiety was synthesized and found to complex paraquat with K-a = 21 000 M(-1) and Delta G degrees = -5.9 kcal mol(-1). The general applicability of the template-directed synthetic procedure developed for porphyrin catenane synthesis was illustrated by the successful isolation of the naphthalene containing porphyrin [2]-catenane 23 in 45% yield. Tetracation exchange processes similar to those for the hydroquinol catenanes were observed, along with an additional process which was found to be the decomplexation/complexation of the naphthalene ring in what is termed an ''out, turn around, and in again'' process similar to that occurring in nonporphyrinic naphthalene [2]-catenanes.

  DOI：

  10.1021/ja00090a029
• 作为产物：
  描述：

  对苯二酚 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 1,4-bis[2-(2-hydroxyethoxy)ethoxy]benzene bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  Molecular meccano. 1. [2]Rotaxanes and a [2]catenane made to order

  摘要：

  A new synthetic strategy for the elaboration of supramolecular species and molecular compounds containing noncovalently interacting components is described, with the long-term objective of constructing highly ordered, wholly synthetic assemblies from readily available starting materials. These could serve as a basis for the future development of mechanoelectrical and photoelectrical communication systems and devices capable of storing and processing information. The approach was conceived against a background of a quarter of a century's experience in supramolecular, alias host-guest, chemistry. It is based on the use of irreversibly interlocked molecular systems that take the form of catenanes and rotaxanes. Such compounds are seen to be the ideal vehicles through which to transfer from supramolecular and host-guest chemistry the knowledge and experience gained from studying complexes between small chemical entities to very much larger molecular assemblies. Once we know how to interlock molecular components irreversibly and efficiently, we shall have a very much clearer idea on how to intertwine related polymer chains reversibly. A number of template-directed syntheses of [2]rotaxanes and a [2]catenane is discussed. They illustrate that there are inherently simple ways of making apparently complex unnatural products from appropriate substrates without the need for reagent control or catalysis. The noncovalent bonding interactions that are used to self-assemble the 1:1 complexes, which serve as precursors to the rotaxanes and the catenane, as well as to the [2]rotaxanes and the [2]catenane themselves, ''live on'' in their structures and superstructures after the self-assembly process is complete. A variety of methods, including X-ray crystallography, fast atom bombardment mass spectrometry, ultra violet-visible, luminescence, nuclear magnetic resonance, and electron spin resonance spectroscopies, and electrochemistry, demonstrate the high structural order that is incorporated into these new molecular assemblies in both the solid and solution states.

  DOI：

  10.1021/ja00027a027

文献信息

• Fluorescent Chemosensors Based on Energy Migration in Conjugated Polymers: The Molecular Wire Approach to Increased Sensitivity
  作者：Qin Zhou、Timothy M. Swager

  DOI：10.1021/ja00155a023

  日期：1995.12

  display a 65-fold enhancement in sensitivity to paraquat as compared to a model monoreceptor fluorescent chemosensor. However, we have determined that delocalization alone is not sufficient to produce facile energy migration, and the more delocalized polythiophenes appear to be less effective at energy migration than the para poly(phenyleneethyny1ene) material. Paraquat-induced fluorescent quenching studies

  我们在此展示了共轭聚合物（分子线）如何用于互连（串联线）受体以产生荧光化学感应系统，其灵敏度比单一受体类似物增强。聚受体材料中的增强机制基于能量迁移方案，其中激发沿聚合物主链扩散。分析物结合产生激发的捕获位点，这导致发射强度大大减弱。研究了结合百草枯的三种不同的环芳基受体系统。这些系统被百草枯结合淬灭，并且相对于单体模型化合物的淬灭增强用于确定能量迁移的效率。研究了两种具有相关聚（苯乙炔）结构的聚合物，并且发现全对位系统比包含元链接的更电子定位的类似物表现出更容易的能量迁移。与模型单受体荧光化学传感器相比，对位多受体系统对百草枯的敏感性提高了 65 倍。然而，我们已经确定单独的离域化不足以产生容易的能量迁移，并且离域化程度更高的聚噻吩在能量迁移方面似乎不如对位聚（苯乙炔）材料有效。还对缺乏环芳烃受体的同源聚合物进行了百草枯诱导的荧光猝灭研究。这些结果表明，能量迁移增强了百草枯的扩散猝灭作用。
• 一种对苯二酚醚链桥连双脲基嘧啶酮化合物及其合成方法
  申请人：常州大学

  公开号：CN109928934A

  公开（公告）日：2019-06-25

  一种对苯二酚醚链桥连脲基嘧啶酮化合物及其合成方法，涉及一种化合物及其合成方法。所述对苯二酚醚链桥连脲基嘧啶酮化合物为基于对苯二酚缩合后的醚链桥连的双脲基嘧啶酮化合物。包括以下步骤：制备一缩乙二醇对甲苯磺酰酯、制备对苯二酚醚链二醇、制备对苯二酚醚链二对甲苯磺酰酯、制备对苯二酚醚链桥连二胺基化合物、制备活化的甲基取代嘧啶酮化合物，最后合成基于对苯二酚醚链桥连双脲基嘧啶酮化合物。该方法原料易得，产率高，所述超分子单体为研究π‑π相互作用控制的多重氢键超分子聚合提供很好的模型，所形成的超分子聚合物以可逆的四重氢键作为连接位点，具有易降解，动态可逆性等优点，具有良好的应用前景。
• Cyclophanes with self-recognising components
  作者：Pier-Lucio Anelli、Masumi Asakawa、Peter R. Ashton、George R. Brown、Wayne Hayes、Oldrich Kocian、Santiago Rodr�guez Pastor、J. Fraser Stoddart、Malcolm S. Tolley、Andrew J. P. White、David J. Williams

  DOI：10.1039/c39950002541

  日期：——

  High dilution techniques have been employed to construct a series of charged flexible cyclophanes comprised of π-electron-rich hydroquinone and π-electron-deficient bipyridinium residues linked by polyether spacer units of varying length: significant conformational changes, leading to intramolecular and intermolecular interactions between the π-donors and π-acceptors, have been observed—as evidenced by X-ray crystallographic and variable temperature 1H NMR and 2D ROESY spectroscopic investigations—within the series of the cyclophanes both in the solid and solution states as a result of increasing the lengths of the polyether spacer units.

  我们采用高稀释技术构建了一系列带电柔性环烷，这些环烷由富含 π 电子的对苯二酚和缺乏 π 电子的联吡啶残基组成，并由不同长度的聚醚间隔单元连接：X 射线晶体学、变温 1H NMR 和 2D ROESY 光谱研究证明，随着聚醚间隔单元长度的增加，在固态和溶液态的环烷系列中，π 供体和π 受体之间的构象发生了重大变化，从而导致分子内和分子间的相互作用。
• Lacunar derivatives of dibenzotetraaza[14]annulene: synthesis and crystal structure of new receptors produced via bis-alkylation of the macrocyclic precursor
  作者：Jarosław Grolik、Krzysztof Zwoliński、Lesław Sieroń、Julita Eilmes

  DOI：10.1016/j.tet.2011.02.010

  日期：2011.4

  The bis(2-hydroxybenzoyl) derivative of dibenzotetraaza[14]annulene was employed as a substrate for producing new lacunar-type receptors. Alkylation of both phenolic OH groups using aliphatic dibromides and ditosylates efficiently leads to the expected bridged products without recourse to a high dilution procedure. Four new dibenzotetraaza[14]annulene-based lacunar receptors, and one unbridged open-chain

  二苯并四氮杂[14]环戊烯的双（2-羟基苯甲酰基）衍生物被用作生产新的腔隙型受体的底物。使用脂族二溴化物和二甲苯磺酸盐对两个酚羟基进行烷基化可有效地产生预期的桥连产物，而无需使用高稀释程序。合成了四个新的基于二苯并四氮杂[14]环的腔隙受体，和一个未桥接的开链双辛氧基类似物。报告了合成程序，分析和光谱表征。基于它们的晶体结构，讨论了产物中大环的构型以及非共价相互作用。
• A Poly(<i>p</i>-phenyleneethynylene) with a Highly Emissive Aggregated Phase
  作者：Robert Deans、Jinsang Kim、Michelle R. Machacek、Timothy M. Swager

  DOI：10.1021/ja0007298

  日期：2000.9.1

  of the emissive properties of conjugatedorganic polymers in the solid-state. It has often been the rule thataggregation of polymer chains results in the undesirable side effectof self-quenching, to the detriment of fluorescence efficiencies.Therefore, a measure of control must be exerted over the structuresadopted by these polymers in the solid-state, if one desires toexploit their emissive properties

  已成为半导体应用的首选材料。链间相互作用是固态共轭有机聚合物发光特性的重要决定因素。聚合物链的聚集通常会导致不希望的自猝灭副作用，从而损害荧光效率。因此，必须对这些聚合物在固态下采用的结构进行控制措施，如果想要利用它们的发光特性。我们之前已经使用共轭聚合物的能量传输特性证明了基于荧光的多受体化学传感器的放大。