N-methyl-2'[2(9,10-bis(dicyanomethylene)anthracenyl)]pyrrolidino[3',4':1,2]-[60]fullerene

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-methyl-2'[2(9,10-bis(dicyanomethylene)anthracenyl)]pyrrolidino[3',4':1,2]-[60]fullerene
• 化学式: C₈₃H₁₃N₅
• 分子量: 1080.05
• InChiKey: ATJYUHSEUIPDHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  88
• 可旋转键数：
  1
• 环数：
  36.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟甲基蒽醌 在 吡啶 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 N-methyl-2'[2(9,10-bis(dicyanomethylene)anthracenyl)]pyrrolidino[3',4':1,2]-[60]fullerene
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753

文献信息

• [60]Fullerene-based electron acceptors with tetracyano-p-quinodimethane (TCNQ) and dicyano-p-quinonediimine (DCNQI) derivatives
  作者：Beatriz Illescas、Nazario Martín、Carlos Seoane

  DOI：10.1016/s0040-4039(97)00220-7

  日期：1997.3

  The first TCNQ and DCNQl derivatives of [60]fullerene are reported. Cyclic voltammetry indicates that the attachment of the first electron in the reduction process takes place in the organic addend. (C) 1997 Elsevier Science Ltd.
• [60]Fullerene Adducts with Improved Electron Acceptor Properties
  作者：Beatriz M. Illescas、Nazario Martín

  DOI：10.1021/jo0003753

  日期：2000.9.1

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.