4,4''-bis[12-(toluene-4-sulfonyloxy)-1,4,7,10-tetraoxadodecyl]biphenyl | 412931-60-3

• 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: 4,4''-bis[12-(toluene-4-sulfonyloxy)-1,4,7,10-tetraoxadodecyl]biphenyl
• 英文别名: 4,4'-bis[11-(p-tolylsulfonyloxy)-3,6,9-trioxaundecyloxy]biphenyl；4,4'-Bis[12-(toluenesulfonyloxy)-4,7,10-trioxadodecyloxy]biphenyl；2-[2-[2-[2-[4-[4-[2-[2-[2-[2-(4-Methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]ethoxy]phenyl]phenoxy]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 412931-60-3
• 化学式: C₄₂H₅₄O₁₄S₂
• 分子量: 847.014
• InChiKey: OUPKVLSMYULUHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  58
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4,4'-二羟基联苯 、 4,4''-bis[12-(toluene-4-sulfonyloxy)-1,4,7,10-tetraoxadodecyl]biphenyl 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以27%的产率得到1,4,7,10,13,26,29,32,35,38-Decaoxa<13.0.13.0>paracyclophan
  参考文献：
  名称：

  Barium Cation Complexation by Flexible Mono- and Ditopic Receptors, Studied by UV Absorption and Fluorescence Spectroscopy

  摘要：

  The metal cation (Ba++) binding ability of a family of designed nonconjugated bichromophoric [bis(para-phenylene)or bis(para-diphenylene)]polyoxamacrocyclic coronands has been studied in acetonitrile in the ground state and in the singlet excited state. The association constants (K) at ambient temperature have been determined from UV absorption and fluorescence data, by use of the LETAGROP-SPEFO programme. The ground state complexes exhibit 1:1 or 1:1 and 2:1 (cation/ligand) stoichiometries and a large variety of association constants, as well as diverse cooperative effects. Remarkably, TTO5O5 {1,4,7,10,13,21,24,27,30,33-decaoxa-[13.15]-(1,4)benzenophane} shows a strong binding ability (log beta = 10.3) with a positive cooperativity. The apparent association constants measured from stationary fluorescence data were found to be lower in some cases than those observed in the ground state; these results strongly suggest that a transitory photodecomplexation between the metal cation and the phenolic oxygen atoms occurs in the S-1 state. An Xray structure analysis was performed on the barium complex of a related podand and the Ba++ coordination number was found to be 10.

  DOI：

  10.1002/1099-0690(20021)2002:2<331::aid-ejoc331>3.0.co;2-e
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 4,4'-二羟基联苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以9%的产率得到4,4''-bis[12-(toluene-4-sulfonyloxy)-1,4,7,10-tetraoxadodecyl]biphenyl
  参考文献：
  名称：

  Barium Cation Complexation by Flexible Mono- and Ditopic Receptors, Studied by UV Absorption and Fluorescence Spectroscopy

  摘要：

  The metal cation (Ba++) binding ability of a family of designed nonconjugated bichromophoric [bis(para-phenylene)or bis(para-diphenylene)]polyoxamacrocyclic coronands has been studied in acetonitrile in the ground state and in the singlet excited state. The association constants (K) at ambient temperature have been determined from UV absorption and fluorescence data, by use of the LETAGROP-SPEFO programme. The ground state complexes exhibit 1:1 or 1:1 and 2:1 (cation/ligand) stoichiometries and a large variety of association constants, as well as diverse cooperative effects. Remarkably, TTO5O5 {1,4,7,10,13,21,24,27,30,33-decaoxa-[13.15]-(1,4)benzenophane} shows a strong binding ability (log beta = 10.3) with a positive cooperativity. The apparent association constants measured from stationary fluorescence data were found to be lower in some cases than those observed in the ground state; these results strongly suggest that a transitory photodecomplexation between the metal cation and the phenolic oxygen atoms occurs in the S-1 state. An Xray structure analysis was performed on the barium complex of a related podand and the Ba++ coordination number was found to be 10.

  DOI：

  10.1002/1099-0690(20021)2002:2<331::aid-ejoc331>3.0.co;2-e

文献信息

• Liquid crystalline paracyclophanes and ansa compounds—series of polyether macrocycles incorporating diacetylene, phenyl, biphenyl, p-terphenyl and 2,5-diphenyl-1,3,4-thiadiazole rigid cores
  作者：Torsten Hegmann、Bernhard Neumann、Raik Wolf、Carsten Tschierske

  DOI：10.1039/b416091f

  日期：——

  Series of different macrocyclic liquid crystals consisting of two rod-like aromatic cores connected at both terminal ends by polyether chains have been synthesised by various macrocyclisation reactions (template assisted etherification, Yamaguchi macrolactonisation, Glaser-coupling reaction). The nature and length of the rigid core have a dominant impact on the liquid crystalline phases formed. A stepwise increase of the length of one of the rigid cores leads to significant mesophase stabilisation, to the induction of lamellar phases and, in general, to wider mesophase ranges. The same types of mesophases but at much reduced transition temperatures are observed when flexible methylene linkages are incorporated into the macrocycles. Parallel pre-organisation of the calamitic cores and micro-segregation of chemically distinct molecular parts are discussed as the main driving forces for the mesophase behaviour of these macrocyclic compounds. Additionally, chiral macrocyclic liquid crystals exhibiting SmC* phases, cholesteric phases and blue phases have been synthesised. In contrast to the cyclophanes, ansa-compounds incorporating only one aromatic core within the macrocycle show either a monotropic nematic phase only or no liquid crystalline behaviour at all. An architecture combining the cyclophane structure with an ansa-unit and a molecule with a non-parallel pre-organisation of rod-like mesogenic cores as well does not show LC phases. The lack of LC behaviour for these compounds might be due to the molecular architecture resulting in a steric disturbance of packing that, in this way, does not allow for segregation of rigid and flexible units into distinct sub-domains.

  由两个棒状芳香核通过聚醚链在两端连接而成的一系列不同的宏环液晶已通过各种宏环化反应合成（模板辅助醚化、山口巨环化反应、格拉泽偶联反应）。刚性核心的性质和长度对形成的液晶相具有显著影响。逐步增加其中一个刚性核心的长度会显著稳定中间相，诱导出层状相，并且总体上扩大了中间相的范围。当将柔性亚甲基链接体引入宏环时，观察到相同类型的中间相，但其相变温度明显降低。讨论了直链核心的平行预先组织和化学不同分子部分的微相分离作为这些宏环化合物中间相行为的主要驱动力。此外，还合成了表现出SmC*相、胆甾相和蓝相的手性宏环液晶。不同于环芳烃，仅在宏环内部包含一个芳香核心的安萨化合物仅显示出单调的向列相或根本没有液晶行为。结合环芳烃结构与安萨单位的架构以及不平行预先组织的棒状介导核心的分子也未显示出液晶相。这些化合物缺乏液晶行为可能是由于分子架构导致的堆积立体障碍，从而不允许刚性和柔性单位分离成不同的子域。
• Binuclear cyclopalladated cyclophanes: towards a new family of metallomesogens
  作者：Bernhard Neumann、Torsten Hegmann、Carsten Tschierske、Bernhard Neumann、Raik Wolf

  DOI：10.1039/a706485c

  日期：——

  Macrocyclic liquid crystals consisting of a biphenyl rigid core and a 2-phenylpyrimidine unit are fused by cyclopalladation giving a novel type of metallomesogens with nematic and smectic mesophases.

  由联苯刚性核心和 2-苯基嘧啶单元组成的大环液晶通过环钯化作用融合，产生了一种具有向列型和遮蔽型中间相的新型金属异构体。
• Synthesis and self-assembly of novel calix[4]arenocrowns: formation of calix[4]areno[2]catenanes
  作者：Lin-Gang Lu、Guang-Ke Li、Xiao-Xia Peng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/j.tetlet.2006.06.108

  日期：2006.8

  A series of novel calix[4]arenocrowns la-c were efficiently synthesized by a one-pot reaction of calix[4]monohydroquinone diacetate 5 with ditosylate 6 and its analogues in the presence of sodium hydroxide. It was found that the calix[4]arenocrowns could form stable pseudorotaxane-type complexes 2a-c with paraquat, and further self-assemble into calix[4]areno[2]catenanes 3a-C with dicationic salt 8 and p-bis(bromomethyl)benzene. (c) 2006 Elsevier Ltd. All rights reserved.
• Barium Cation Complexation by Flexible Mono- and Ditopic Receptors, Studied by UV Absorption and Fluorescence Spectroscopy
  作者：Ezequiel Perez-Inestrosa、Jean-Pierre Desvergne、Henri Bouas-Laurent、Jean-Claude Rayez、Marie-Thérèse Rayez、Michel Cotrait、Pierre Marsau

  DOI：10.1002/1099-0690(20021)2002:2<331::aid-ejoc331>3.0.co;2-e

  日期：2002.1

  The metal cation (Ba++) binding ability of a family of designed nonconjugated bichromophoric [bis(para-phenylene)or bis(para-diphenylene)]polyoxamacrocyclic coronands has been studied in acetonitrile in the ground state and in the singlet excited state. The association constants (K) at ambient temperature have been determined from UV absorption and fluorescence data, by use of the LETAGROP-SPEFO programme. The ground state complexes exhibit 1:1 or 1:1 and 2:1 (cation/ligand) stoichiometries and a large variety of association constants, as well as diverse cooperative effects. Remarkably, TTO5O5 1,4,7,10,13,21,24,27,30,33-decaoxa-[13.15]-(1,4)benzenophane} shows a strong binding ability (log beta = 10.3) with a positive cooperativity. The apparent association constants measured from stationary fluorescence data were found to be lower in some cases than those observed in the ground state; these results strongly suggest that a transitory photodecomplexation between the metal cation and the phenolic oxygen atoms occurs in the S-1 state. An Xray structure analysis was performed on the barium complex of a related podand and the Ba++ coordination number was found to be 10.