2,6,10,14-Tetraoxatetracyclo[13.6.6.016,21.022,27]heptacosa-1(21),15,17,19,22,24,26-heptaene-7,9-dione | 433718-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6,10,14-Tetraoxatetracyclo[13.6.6.016,21.022,27]heptacosa-1(21),15,17,19,22,24,26-heptaene-7,9-dione
• 英文别名: 2,6,10,14-tetraoxatetracyclo[13.6.6.016,21.022,27]heptacosa-1(21),15,17,19,22,24,26-heptaene-7,9-dione
• CAS: 433718-09-3
• 化学式: C₂₃H₂₂O₆
• 分子量: 394.424
• InChiKey: UNAZWHDKRQBHAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  足球烯 、 2,6,10,14-Tetraoxatetracyclo[13.6.6.016,21.022,27]heptacosa-1(21),15,17,19,22,24,26-heptaene-7,9-dione 在 四溴化碳 、 diazabicycloundecane 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以32%的产率得到
  参考文献：
  名称：

  Th-Symmetrical Hexakisadducts of C60 with a Densely Packed π-Donor Shell Can Act as Energy- or Electron-Transducing Systems

  摘要：

  For the first time several T-h-symmetrical hexakisadducts of C-60 bearing up to six electro and photoactive o-phenylene diamine or 9,10-dialkoxyanthracene moieties were synthesized and subjected to photoinduced electron/energy-transfer studies. Both donors form a densely packed pi-donor shell surrounding the fullerene core. In these novel core -shell ensembles (7 and 19), either an efficient energy transfer from the dialkoxyanthracene periphery, or an electron transfer from the o-phenylene diamine periphery transduces the flow of excited-state energy or electrons, respectively, to the fullerene moiety, which resides in the central core. Due to the relatively high reduction potential of the fullerene core, which is anodically shifted by approximate to 0.7 V, compared with that of pristine C-60, the outcome of these intra- molecular reactions depends mainly on the donor ability of the peripheral system. Interestingly, the charge-separated state in the o-phenylene diamine heptad (7; tau = 2380 ns in benzonitrile) is stabilized by a factor of 20 relative to the corresponding o-phenylene diamine dy-ad (6; tau = 120 ns in benzonitrile), an effect that points unequivocally to the optimized storage of charges in this highly functionalized fullerene ensemble.

  DOI：

  10.1002/1521-3765(20020215)8:4<979::aid-chem979>3.0.co;2-6
• 作为产物：
  描述：

  氫蒽醌 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 2,6,10,14-Tetraoxatetracyclo[13.6.6.016,21.022,27]heptacosa-1(21),15,17,19,22,24,26-heptaene-7,9-dione
  参考文献：
  名称：

  Th-Symmetrical Hexakisadducts of C60 with a Densely Packed π-Donor Shell Can Act as Energy- or Electron-Transducing Systems

  摘要：

  For the first time several T-h-symmetrical hexakisadducts of C-60 bearing up to six electro and photoactive o-phenylene diamine or 9,10-dialkoxyanthracene moieties were synthesized and subjected to photoinduced electron/energy-transfer studies. Both donors form a densely packed pi-donor shell surrounding the fullerene core. In these novel core -shell ensembles (7 and 19), either an efficient energy transfer from the dialkoxyanthracene periphery, or an electron transfer from the o-phenylene diamine periphery transduces the flow of excited-state energy or electrons, respectively, to the fullerene moiety, which resides in the central core. Due to the relatively high reduction potential of the fullerene core, which is anodically shifted by approximate to 0.7 V, compared with that of pristine C-60, the outcome of these intra- molecular reactions depends mainly on the donor ability of the peripheral system. Interestingly, the charge-separated state in the o-phenylene diamine heptad (7; tau = 2380 ns in benzonitrile) is stabilized by a factor of 20 relative to the corresponding o-phenylene diamine dy-ad (6; tau = 120 ns in benzonitrile), an effect that points unequivocally to the optimized storage of charges in this highly functionalized fullerene ensemble.

  DOI：

  10.1002/1521-3765(20020215)8:4<979::aid-chem979>3.0.co;2-6

文献信息

• Macrocyclic Cyclo[n]malonates – Synthetic Aspects and Observation of Columnar Arrangements by X-ray Crystallography
  作者：Nikos Chronakis、Torsten Brandmüller、Christian Kovacs、Uwe Reuther、Wolfgang Donaubauer、Frank Hampel、Felix Fischer、François Diederich、Andreas Hirsch

  DOI：10.1002/ejoc.200500921

  日期：2006.5

  interest are the macrocyclic bismalonates, as they show pronounced crystallisability and arrange into columnar motifs in the solid state. They feature distinctive dihedral angles: all ester moieties adopt anti conformations whereas the planes of the carboxy moieties of each malonate residue arrange in an approximately orthogonal fashion. The latter geometry is enforced by the macrocyclic structures, as

  通过丙二酰二氯与α,ω-二醇缩合，一步法合成了多种非手性和手性大环低聚丙二酸酯。我们通过改变二醇中间隔物的长度和类型研究了这种方法的适用性。产品分布分析表明，单体、二聚或三聚大环丙二酸酯的优先形成可以通过选择具有连接羟基的特定间隔基的二醇来控制。特别令人感兴趣的是大环双丙二酸酯，因为它们显示出明显的结晶性并在固态下排列成柱状图案。它们具有独特的二面角：所有酯部分都采用反构象，而每个丙二酸酯残基的羧基部分的平面以近似正交的方式排列。正如剑桥结构数据库中的构象搜索所揭示的那样，后一种几何结构由大环结构强制执行。X 射线衍射数据表明，C=O...H-C 和 C-O...H-C 氢键稳定了二聚环的柱状排列并形成管状组件。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Th-Symmetrical Hexakisadducts of C60 with a Densely Packed π-Donor Shell Can Act as Energy- or Electron-Transducing Systems
  作者：Michael Diekers、Chuping Luo、Dirk M. Guldi、Andreas Hirsch

  DOI：10.1002/1521-3765(20020215)8:4<979::aid-chem979>3.0.co;2-6

  日期：2002.2.15

  For the first time several T-h-symmetrical hexakisadducts of C-60 bearing up to six electro and photoactive o-phenylene diamine or 9,10-dialkoxyanthracene moieties were synthesized and subjected to photoinduced electron/energy-transfer studies. Both donors form a densely packed pi-donor shell surrounding the fullerene core. In these novel core -shell ensembles (7 and 19), either an efficient energy transfer from the dialkoxyanthracene periphery, or an electron transfer from the o-phenylene diamine periphery transduces the flow of excited-state energy or electrons, respectively, to the fullerene moiety, which resides in the central core. Due to the relatively high reduction potential of the fullerene core, which is anodically shifted by approximate to 0.7 V, compared with that of pristine C-60, the outcome of these intra- molecular reactions depends mainly on the donor ability of the peripheral system. Interestingly, the charge-separated state in the o-phenylene diamine heptad (7; tau = 2380 ns in benzonitrile) is stabilized by a factor of 20 relative to the corresponding o-phenylene diamine dy-ad (6; tau = 120 ns in benzonitrile), an effect that points unequivocally to the optimized storage of charges in this highly functionalized fullerene ensemble.