1-hydroxy-9-(2-chlorobenzoyl)oxy-1,9-dihydro(C60-Ih)[5,6]fullerene | 1381936-35-1

• 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: 1-hydroxy-9-(2-chlorobenzoyl)oxy-1,9-dihydro(C60-Ih)[5,6]fullerene
• CAS: 1381936-35-1
• 化学式: C₆₇H₅ClO₃
• 分子量: 893.228
• InChiKey: UXDXQYAEBGPDCT-SIKJLATJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.71
• 重原子数：
  71.0
• 可旋转键数：
  2.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  邻氯苯甲酰氯 、 足球烯 在 iron perchlorate hexahydrate 作用下， 以 邻二氯苯 为溶剂， 反应 0.66h， 以24%的产率得到1-hydroxy-9-(2-chlorobenzoyl)oxy-1,9-dihydro(C60-Ih)[5,6]fullerene
  参考文献：
  名称：

  Ferric Perchlorate-Mediated Synthesis of 1,2-Fullerenols C₆₀(OCOR)(OH)

  摘要：

  1,2-Fullerenols C-60(OCOR)(OH) have been facilely synthesized via the one-step reaction of [60]fullerene with acid chlorides promoted by ferric perchlorate. A possible reaction mechanism for the product formation is proposed.

  DOI：

  10.1021/jo301202g

文献信息

• FeCl₃-Mediated Synthesis of Fullerenyl Esters as Low-LUMO Acceptors for Organic Photovoltaic Devices
  作者：Masahiko Hashiguchi、Naoki Obata、Masashi Maruyama、Kee Sheng Yeo、Takao Ueno、Tomohiko Ikebe、Isao Takahashi、Yutaka Matsuo

  DOI：10.1021/ol301186u

  日期：2012.7.6

  C-60 reacted with aromatic and aliphatic carboxylic acids in the presence of inexpensive FeCl3 at room temperature to produce hydroxyfullerenyl esters C-60(OCOR)(OH) in up to 68% isolated yield. The hydroxyl group was utilized in functional group transformations to obtain a diester derivative C-60(OCOAr)(OCOPh) (Ar = 2,6-xylyl) and a siloxyl derivative C-60(OCOAr)(OSiMe3). The diester and siloxyl derivatives were found to possess low-lying LUMO levels were utilized in organic photovoltaic devices showing 1.3% power conversion efficiency.