N-methyl-2-[2,4,6-tris(octyloxy)phenyl]fulleropyrrolidine

• 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-[2,4,6-tris(octyloxy)phenyl]fulleropyrrolidine
• 英文别名: N-methyl-2-[2,4,6-tri(octyloxy)phenyl]fulleropyrridine；N-methyl-2-[2,4,6-tri(octyloxy)phenyl]fulleropyrrolidine
• 化学式: C₉₃H₅₉NO₃
• 分子量: 1238.5
• InChiKey: FUHPOWAGLUOVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.3
• 重原子数：
  97
• 可旋转键数：
  25
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间苯三酚甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 N-methyl-2-[2,4,6-tris(octyloxy)phenyl]fulleropyrrolidine
  参考文献：
  名称：

  Room Temperature Liquid Fullerenes:  An Uncommon Morphology of C₆₀ Derivatives

  摘要：

  Room temperature liquid C60 derivatives bearing a 2,4,6-trialkyloxyphenyl branch show a dramatic decrease in viscosity with an increase in the length of the alkyl chains. This feature, when combined with electrochemical activities similar to those of pristine C60 and relatively high charge carrier mobility, makes them an extremely attractive novel carbon material for future applications in materials science.

  DOI：

  10.1021/ja063866z

文献信息

• Liquid Fullerene Derivative, Method for Producing the Same, and Device Using the Same
  申请人：Nakanishi Takashi

  公开号：US20100019205A1

  公开（公告）日：2010-01-28

  The liquid fullerene derivative according to the present invention contains a fullerene moiety, a benzene ring bonded to the fullerene moiety, and first to third alkyl substituents R 1 , R 2 and R 3 bonded to 2-, 4- and 6-positions of the benzene ring, respectively, and the first to third alkyl substituents R 1 , R 2 and R 3 each contain at least 12 carbon atoms. The liquid fullerene derivative which is liquid at room temperature without requiring a solvent and easily exhibits the function of the fullerene itself, a method for producing the same, and a device using the same are provided.

  根据本发明，液态富勒烯衍生物包含一个富勒烯基团，一个与富勒烯基团结合的苯环，以及第一至第三烷基取代基R1、R2和R3分别结合在苯环的2-、4-和6-位置上，且第一至第三烷基取代基R1、R2和R3各自含有至少12个碳原子。该液态富勒烯衍生物在室温下为液态，无需溶剂，并且很容易展现出富勒烯本身的功能，提供了一种生产该液态富勒烯衍生物的方法以及使用该液态富勒烯衍生物的装置。
• Structural Requirements for Producing Solvent-Free Room Temperature Liquid Fullerenes
  作者：Tsuyoshi Michinobu、Kensuke Okoshi、Yoshihiko Murakami、Kiyotaka Shigehara、Katsuhiko Ariga、Takashi Nakanishi

  DOI：10.1021/la400969f

  日期：2013.4.30

  A new class of solvent-free room temperature liquid fullerenes was synthesized by attaching a single substituent of 1,3,5-tris(alkyloxy)benzene unit to C-60 or C-70 under the Prato conditions. Although the C-60 monoadducts were single components after chromatographic purification, the C-70 monoadducts were isomeric mixtures due to the prolate spheroidal pi-chromophore. The alkyl chain length of the substituents significantly affected both melting points and rheological behavior of the fullerene derivatives. When the alkyl chains were short, the intermolecular pi-pi interactions of adjacent fullerene cores led to a melting point higher than room temperature. In contrast, in the case of exceedingly long alkyl chains, such as eicosyl (-C20H41) and docosanyl (-C22H45) groups, the van der Waals interactions among neighboring alkyl chains became dominant. Accordingly, only medium alkyl chain lengths could provide solvent-free fluidic fullerenes with low melting points. The rheological measurements of the liquid fullerenes at 25 degrees C revealed their unique liquid characteristics; molecular-level friction (or viscosity) and nanometer-scale clustering were noticed. It is generally thought that alkyl chains serve as a stabilizer of the fullerene core units. Thus, a longer chain or higher plasticity of the stabilizers would promote the disturbance of the core core interactions. It was indeed shown that longer alkyl chains resulted in a lower fluid viscosity. It was also found that metastable solid phases were produced by the noticeable van der Waals interaction between the long alkyl chains especially when a symmetric C-60 core was adopted. This interesting finding enabled the comparison of electrochemical activities of the C-60 unit between the solvent free liquid and metastable solid form, which revealed a superior electrochemical activity in the liquid state.