bis-[(2,2'-bipyridine-5,5'-diyl)dimethyl]-bis-p-tert-calix[4]aren | 158750-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: bis-[(2,2'-bipyridine-5,5'-diyl)dimethyl]-bis-p-tert-calix[4]aren
• 英文别名: 18,24,30,49,55,61,66,79-Octatert-butyl-3,14,34,45-tetraoxa-7,10,38,41-tetrazapentadecacyclo[45.15.7.716,32.25,8.29,12.236,39.240,43.122,26.153,57.164,68.02,59.015,20.028,33.046,51.177,81]octaoctaconta-1,5,7,9,11,15,17,19,22,24,26(83),28,30,32,36,38,40,42,46,48,50,53(71),54,56,59,61,64,66,68(70),72,74,77(88),78,80,84,86-hexatriacontaene-70,71,83,88-tetrol；18,24,30,49,55,61,66,79-octatert-butyl-3,14,34,45-tetraoxa-7,10,38,41-tetrazapentadecacyclo[45.15.7.716,32.25,8.29,12.236,39.240,43.122,26.153,57.164,68.02,59.015,20.028,33.046,51.177,81]octaoctaconta-1,5,7,9,11,15,17,19,22,24,26(83),28,30,32,36,38,40,42,46,48,50,53(71),54,56,59,61,64,66,68(70),72,74,77(88),78,80,84,86-hexatriacontaene-70,71,83,88-tetrol
• CAS: 158750-25-5
• 化学式: C₁₁₂H₁₂₈N₄O₈
• 分子量: 1658.27
• InChiKey: UYZYDJUXEIPXIZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.117±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  28.5
• 重原子数：
  124
• 可旋转键数：
  8
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,5'-二溴甲基-2,2'-联吡啶 、 bis-[(2,2'-bipyridine-5,5'-diyl)dimethyl]-bis-p-tert-calix[4]aren 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以4%的产率得到
  参考文献：
  名称：

  Calix[4]Arene Podands and Barrelands Incorporating 2,2″-Bipyridine Moieties and Their Lanthanide Complexes: Luminescence Properties

  摘要：

  AbstractA new family of cone‐shaped podands and barrel‐shaped cryptands based on calix[4]arenes incorporating 5,5′‐substituted 2,2′‐bipyridine subunits were prepared and characterized. The Eu3+ and Tb3+ complexes of the podands bearing two, three, or four bipyridine chromophores could be isolated. High molar absorption coefficients (εmax = 39 600M−1 cm−1 for Eu4 and 26 700M−1 cm−1 for Eu3) and high metal luminescence quantum yields (16% for Eu4 and 15% for Eu3) were obtained. Molecular dynamics simulations on Eu4 showed that the bipyridine arms wrap around the lanthanide cation, efficiently shielding the cation from solvent molecules. In the presence of chloride counter‐ions the fourth bipyridine arms does not coordinate the lanthanide ion. Ligands bearing two bipyridine units and two additional functional groups—ethyl butyrate or N‐propylpyrrole—did not give stable lanthanide complexes. The barre‐land containing two calix[4]arene moieties and four bipyridine groups did not form complexes with lanthanide ions, most probably because of the rigidity of the ligand.

  DOI：

  10.1002/chem.19970031114
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 5,5'-二溴甲基-2,2'-联吡啶 在 NaCO₃ 作用下， 以23%的产率得到bis-[(2,2'-bipyridine-5,5'-diyl)dimethyl]-bis-p-tert-calix[4]aren
  参考文献：
  名称：

  基于5,5'-取代的2,2'-联吡啶亚基的杯杯芳烃[4]-足和桶形杯杯芳烃[4] -cryptands

  摘要：

  新颖的合成和初步镧系元素络合研究顺-1,3-双- [（5-甲基-2,2'-联吡啶-5'-基）甲基] -对-叔-calix [4]芳烃大号3和四[[（5-甲基-2,2'-联吡啶-5'-基）甲基]-对-叔-杯[4]芳烃L 4链烷和新的双[[（2,2'-联吡啶-5， 5'-二基）二甲基]-双-对-叔杯[4]芳烃L 5和四-[（2,2'-联吡啶-5,5'-二基）二甲基]-双-对叔-杯描述了具有桶形结构的[4]芳烃L 6穴状配体。

  DOI：

  10.1016/s0040-4039(00)73416-2

文献信息

• Calixarene[4]-podands and barrel-shaped calixarene[4]-cryptands based on 5,5′-substituted-2,2′-bipyridine subunits
  作者：Gilles Ulrich、Raymond Ziessel

  DOI：10.1016/s0040-4039(00)73416-2

  日期：1994.8

  preliminary lanthanides complexation studies of novel syn-1,3-bis-[(5-methyl-2,2′-bipyridine-5′-yl)methyl]-p-tert-calix[4]arene L3 and tetra-[(5-methyl-2,2′-bipyridine-5′-yl)methyl]-p-tert-calix[4]arene L4 podands and new bis-[(2,2′-bipyridine-5,5′-diyl)dimethyl]-bis-p-tert-calix[4]arene L5 and tetra-[(2,2′-bipyridine-5,5′-diyl)dimethyl]-bis-p-tert-calix[4]arene L6 cryptands with a barrel-shaped structure

  新颖的合成和初步镧系元素络合研究顺-1,3-双- [（5-甲基-2,2'-联吡啶-5'-基）甲基] -对-叔-calix [4]芳烃大号3和四[[（5-甲基-2,2'-联吡啶-5'-基）甲基]-对-叔-杯[4]芳烃L 4链烷和新的双[[（2,2'-联吡啶-5， 5'-二基）二甲基]-双-对-叔杯[4]芳烃L 5和四-[（2,2'-联吡啶-5,5'-二基）二甲基]-双-对叔-杯描述了具有桶形结构的[4]芳烃L 6穴状配体。
• Nitroxo spin-labelled calix[4]arene podands and cryptands: Allosteric regulation of spin-spin exchange interaction
  作者：Gilles Ulrich、Philippe Turek、Raymond Ziessel

  DOI：10.1016/s0040-4039(96)02042-4

  日期：1996.11

  Hybrid calix[4]arene podands and ctyptands, each bearing two or four stable nitronyl-nitroxide radicals and two bipyridine subunits, exhibit through-space exchange interaction, the magnitude of which can be modulated by coordination of ZM(2+) cations at the bipyridine sites. Copyright (C) 1996 Elsevier Science Ltd
• Doubly bridged biscalix[4]arene for homotropic and heterotropic allosteric effects on ion recognition
  作者：Tatsuya Nabeshima、Toshiyuki Saiki、Keiko Sumitomo、Shigehisa Akine

  DOI：10.1016/j.tetlet.2004.04.088

  日期：2004.6

  A novel host, which shows homotropic and heterotropic allostery for Na+ and Ag+ recognition, is constructed by utilizing a biscalix[4]arene skeleton bearing bipyridine and ester moieties. The host binds two Na+ ions, but the second binding to Na+ is considerably suppressed by the first Na+ ion bound in the other binding site. (C) 2004 Elsevier Ltd. All rights reserved.
• Calix[4]Arene Podands and Barrelands Incorporating 2,2″-Bipyridine Moieties and Their Lanthanide Complexes: Luminescence Properties
  作者：Gilles Ulrich、Raymond Ziessel、Ilse Manet、Massimo Guardigli、Nanda Sabbatini、Franca Fraternali、Georges Wipff

  DOI：10.1002/chem.19970031114

  日期：1997.11

  AbstractA new family of cone‐shaped podands and barrel‐shaped cryptands based on calix[4]arenes incorporating 5,5′‐substituted 2,2′‐bipyridine subunits were prepared and characterized. The Eu3+ and Tb3+ complexes of the podands bearing two, three, or four bipyridine chromophores could be isolated. High molar absorption coefficients (εmax = 39 600M−1 cm−1 for Eu4 and 26 700M−1 cm−1 for Eu3) and high metal luminescence quantum yields (16% for Eu4 and 15% for Eu3) were obtained. Molecular dynamics simulations on Eu4 showed that the bipyridine arms wrap around the lanthanide cation, efficiently shielding the cation from solvent molecules. In the presence of chloride counter‐ions the fourth bipyridine arms does not coordinate the lanthanide ion. Ligands bearing two bipyridine units and two additional functional groups—ethyl butyrate or N‐propylpyrrole—did not give stable lanthanide complexes. The barre‐land containing two calix[4]arene moieties and four bipyridine groups did not form complexes with lanthanide ions, most probably because of the rigidity of the ligand.