1',4'-dimethyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9]-(C₆₀-I_h)[5,6]fullerene | 151467-69-5

• 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',4'-dimethyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9]-(C₆₀-I_h)[5,6]fullerene
• 英文别名: N,N'-dimethylethylenediamine-[60]-fullerene
• CAS: 151467-69-5
• 化学式: C₆₄H₁₀N₂
• 分子量: 806.797
• InChiKey: QUCPOMORZVVXBF-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  2.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  66
• 可旋转键数：
  0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1',4'-dimethyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9]-(C₆₀-I_h)[5,6]fullerene 、 copper(ll) bromide 以 四氢呋喃 为溶剂， 以79%的产率得到(N,N'-dimethylethylenediamine-[60]-fullerene)copper(II) bromide
  参考文献：
  名称：

  扩展巴克敏斯特富勒烯的配位化学：(N,N'-二甲基乙二胺-[60]-富勒烯)溴化铜(II)的合成与表征

  摘要：

  摘要 通过滴加 N,N'-二甲基乙二胺-[60]-富勒烯的四氢呋喃溶液合成螯合物（N,N'-二甲基乙二胺-[60]-富勒烯）溴化铜（II），产率 79%。 (THF) 到过量的溴化铜 (II) 在 THF 中的溶液。所得棕色沉淀物通过电子自旋共振 (ESR) 光谱和元素分析表征。

  DOI：

  10.1016/j.inoche.2004.05.013
• 作为产物：
  描述：

  足球烯 、 N,N'-二甲基乙二胺 在 4-二甲氨基吡啶 、 copper diacetate 作用下， 以 氯苯 为溶剂， 反应 4.0h， 以14%的产率得到1',4'-dimethyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9]-(C₆₀-I_h)[5,6]fullerene
  参考文献：
  名称：

  Cu(OAc)₂-promoted reaction of [60]fullerene with primary amines or diamines

  摘要：

  Cu(OAc)2介导的氧化脱氢加成反应可以将易得的一级胺加成到C60上，从而简洁地制备出环氧丙烷基富勒烯。此外，Cu(OAc)2促进的C60与二元胺的反应可以得到C60融合的环状1,2-二胺基富勒烯。

  DOI：

  10.1039/c5ob01048a

文献信息

• Sonochemical synthesis of 1',4'-dialkyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9](C60-Ih)[5,6]fullerenes
  作者：Zemfira S. Kinzyabaeva

  DOI：10.1007/s10593-021-02950-2

  日期：2021.5

  For the first time, a selective and efficient method for the synthesis of 1',4'-dialkyl-1',4',5',6'-tetrahydropyrazino[2',3':1,9](С60-Ih)[5,6]-fullerenes (alkyl = methyl, ethyl, isopropyl) was developed based on the reaction of C60 fullerene with N-substituted ethylenediamines in PhMe–DMF medium effected by ultrasound.

  首次采用选择性高效的方法合成1',4'-二烷基-1',4',5',6'-四氢吡嗪并[2',3':1,9](С 60 - I h )[5,6]-富勒烯（烷基 = 甲基、乙基、异丙基）是基于 C 60富勒烯与N-取代的乙二胺在 PhMe-DMF 介质中通过超声波的反应而开发的。
• Kampe, Klaus-Dieter; Egger, Norbert, Liebigs Annalen, 1995, # 1, p. 115 - 124
  作者：Kampe, Klaus-Dieter、Egger, Norbert

  DOI：——

  日期：——
• Photochemical addition reactions of [60]fullerene with 1,2-ethylenediamine and piperazine
  作者：Nai-Xing Wang

  DOI：10.1016/s0040-4020(02)00123-0

  日期：2002.3

  N,N'-Dimethylethylenediamine and piperazine reacted with [60]fullerene by photoinduced-electron transfer to form the adduct compounds in a short reaction time with a good yield. NMR spectroscopy showed unambiguously that derivatives were C-2nu symmetric structures with a 6,6 junction, and a single-electron transfer intermediate was suggested. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Photoinduced Intramolecular n−π* Electron Transfer in Aminofullerene Derivatives
  作者：Ya-Ping Sun、Bin Ma、Christopher E. Bunker

  DOI：10.1021/jp982591+

  日期：1998.9.1

  The photophysical properties of two amino-C-60 derivatives, which are adducts of C-60 With N,N'-dimethyl-1,2-ethylenediamine and C-60 With piperazine, were studied systematically. The results show that there is intramolecular n (amino groups) to pi* (photoexcited fullerene cage) electron transfer in the aminofullerene molecules. The photoinduced electron transfer can be observed only in a polar solvent environment for the first compound and also in polarizable solvents for the second compound. As a result, the fluorescence quantum yields and lifetimes and the nonlinear absorptive optical Limiting responses of the amino-C-60 derivatives are strongly solvent dependent. Charge-transfer excited states are formed following electron transfer in both compounds, but only that of the second compound is emissive. There is also evidence for delayed fluorescence in polar solvents, which is probably due to the vertical excited singlet state repopulated from the charge-transfer excited state, However, the fluorescence quenchings and effects on optical limiting in polar solvents can be eliminated through protonating amino groups in the molecules by adding a small amount of trifluoroacetic acid into the sample solutions. Although the intramolecular n-pi* electron transfer in aminofullerenes shares some characteristics with the classical twisted intramolecular charge transfer in molecules represented by p-N,N-dimethylaminobenzonitrile, the amino-C-60 derivatives are in fact better classified as redox dyads. Since electron donor (amino groups) and acceptor (fullerene cage) are linked directly through only sp(3) carbons, these are the simplest donor-spacer-fullerene dyads. In more quantitative treatments, electron-transfer rate constants for the amino-C-60 derivatives under different solvent conditions were correlated with the solvent microscopic polarities, which were estimated using the strongly solvatochromic molecular probe 6-propionyl-2-(N,N-dimethylamino)naphthalene.
• Photophysical and Nonlinear Optical Properties of [60]Fullerene Derivatives
  作者：Ya-Ping Sun、Glenn E. Lawson、Jason E. Riggs、Bin Ma、Naixing Wang、Dwella K. Moton

  DOI：10.1021/jp9801121

  日期：1998.7.1

  A systematic spectroscopic study of a series of C-60 derivatives with different cage functionalizations is reported. The absorption spectra and absorptivities of the derivatives in solution were measured and compared. By recording the fluorescence spectra using a near-infrared-sensitive emission spectrometer (extending to 1200 nm), fluorescence quantum yields of the derivatives were determined quantitatively, Fluorescence lifetimes of the derivatives were obtained using the time-correlated single photon counting technique. The results show that both fluorescence quantum yields and lifetimes are rather similar for the different classes of C60 derivatives. The nonlinear absorptive properties of the derivatives were evaluated by optical limiting measurements in solution and in polymer film using the second harmonic of a Q-switched Nd:Yag laser at 532 nm, Effects of different fullerene cage functionalizations on the photophysical properties and optical limiting responses of the C-60 derivatives are discussed.