1-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine | 174278-67-2

• 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-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine
• 英文别名: N-methyl-2-(p-methoxyphenyl)-3,4-fulleropyrrolidine
• CAS: 174278-67-2
• 化学式: C₇₀H₁₃NO
• 分子量: 883.879
• InChiKey: XNJGZVDJBOCTLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  72
• 可旋转键数：
  2
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine 反应 0.08h， 以99%的产率得到足球烯
  参考文献：
  名称：

  Metal-free, retro-cycloaddition of fulleropyrrolidines in ionic liquids under microwave irradiation

  摘要：

  在微波辐照下，离子液体可在几分钟内将富勒吡咯烷定量环化为 [60] 富勒烯，而无需任何其他添加剂。

  DOI：

  10.1039/b906813a
• 作为产物：
  描述：

  以 氯苯 为溶剂， 生成 四(二甲氨基)乙烯 、 1-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine
  参考文献：
  名称：

  Linear free-energy relationship for electron-transfer processes of pyrrolidinofullerenes with tetrakis(dimethylamino)ethylene in ground and excited states

  摘要：

  吡咯烷富勒烯基态和激发三重态电子转移过程的系统研究{C60(C3H6N)R [R=H (1), p-C6H4NO2 (2), p-C6H4CHO (3), p-C6H5 (4) )、p-C6H4OMe (5)、p-C6H4NMe2 (6)]} 与四(二甲氨基)乙烯 (TDAE) 的结合已通过可见光近红外区域的稳态和瞬态吸收测量进行。对基态电子转移过程平衡的分析表明，极性溶剂中会产生自由基。通过激光闪光光解对基态电子转移反应的平衡施加扰动，观察到通过 T(C60(C3H6N)R)* 的光诱导电子转移过程。根据热力学数据和动力学数据的关系，可以评估基态的电子转移速率常数（ketG）。与极性溶剂中的平衡常数(K)相比，ketG值受取代基的影响较小； α=0.6 in Δ log ketG=α Δ log K。该α值表明基态中正向电子转移的活化能随(C60(C3H6N)R)-的热力学稳定性适度变化。通过 T(C60(C3H6N)R)* 的电子转移速率常数接近扩散控制极限，由于其高放热过程，没有表现出大的取代基效应 (α'=0)。这种线性自由能关系可以扩展到其他体系，例如T(C60(C3H6N)R)*/N,N-二甲基苯胺，从中可以获得电子转移过程的有价值的信息。

  DOI：

  10.1039/a901837i

文献信息

• Microwave-Assisted Functionalization of Carbon Nanostructures in Ionic Liquids
  作者：Ivan Guryanov、Francesca Maria Toma、Alejandro Montellano López、Mauro Carraro、Tatiana Da Ros、Guido Angelini、Eleonora D'Aurizio、Antonella Fontana、Michele Maggini、Maurizio Prato、Marcella Bonchio

  DOI：10.1002/chem.200901408

  日期：2009.11.23

  includes aliphatic, aromatic, and fluorous‐tagged (FT) derivatives. MW irradiation of IL‐structured bucky gels is instrumental for the functionalization of single‐walled carbon nanotubes (SWNTs), yielding group coverages of up to one functional group per 60 carbon atoms of the SWNT network. An improved performance is obtained in low viscosity bucky gels, in the order [bmim]BF4> [omim]BF4> [hvim]TF2N

  通过筛选关于IL介质组成，施加的MW功率和同时冷却的反应方案，研究了微波（MW）辐照和离子液体（IL）对偶氮甲硫烷基到[60]富勒烯的环加成反应的影响。系统的。[60]使用IL 1-甲基-3-正辛基咪唑四氟硼酸酯（[omim] BF 4）和邻苯二甲醛的1：3混合物，可在2-10分钟内实现高达98％的富勒烯转化率。二氯苯，施加的功率低至12W。可以根据富勒烯浓度对[60]富勒烯的单加成与多加成选择性进行调节。反应范围包括脂族，芳族和氟标签（FT）衍生物。IL结构的Bucky凝胶的MW辐射有助于单壁碳纳米管（SWNT）的功能化，从而使SWNT网络中每60个碳原子最多覆盖一个官能团。在低粘度的Bucky凝胶中，按[bmim] BF 4 > [omim] BF 4 > [hvim] TF 2 N的顺序可获得更好的性能（bmim = 1-甲基-3-正丁基咪唑； hvim = 1-乙烯基-3- n十六
• Design, synthesis and photophysical studies of phenylethynyl-bridged phthalocyanine-fullerene dyads
  作者：Jaro Arero、Gerdenis Kodis、Robert A. Schmitz、Dalvin D. Méndez-Hernández、Thomas A. Moore、Ana L. Moore、Devens Gust

  DOI：10.1142/s1088424615500662

  日期：2015.8

  excitation of the zinc phthalocyanine is followed by rapid establishment of an equilibrium between the phthalocyanine and fullerene excited states. These excited states decay mainly to the ground state and the respective triplet states. The fullerene triplet then transfers its energy to form the phthalocyanine triplet. About 20% of the phthalocyanine excited states lead to formation of a charge-separated state

  采用新的合成路线制备了锌和游离碱酞菁-富勒吡咯烷二联体，其中发色团通过苯乙炔基连接，并研究了它们的光电化学性质。锌对易溶于多种溶剂，其光谱性质已在甲苯和苯甲腈中测定。在甲苯中，酞菁锌的激发之后，酞菁和富勒烯激发态之间的平衡迅速建立。这些激发态主要衰变为基态和各自的三重态。然后富勒烯三重态转移其能量以形成酞菁三重态。大约 20% 的酞菁激发态导致形成电荷分离态。在苯甲腈中，观察到相同的衰变途径，但光致电子转移要快得多，并产生量子产率≥85%的电荷分离态。电荷分离状态在甲苯中的寿命为 2.8 ns，在苯甲腈中为 94 ps。
• Solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes under high-speed vibration milling
  作者：Guan-Wu Wang、Ting-Hu Zhang、Er-Hong Hao、Li-Juan Jiao、Yasujiro Murata、Koichi Komatsu

  DOI：10.1016/s0040-4020(02)01478-3

  日期：2003.1

  The solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes (RCHO) 2a-e under high-speed vibration milling (HSVM) conditions have been investigated. Fulleropyrrolidines 4a-e (C-60(CH2N(CH3)CHR), R=H (4a), C6H5 (4b), pNO(2)-C6H5 (4c), p-CH3O-C6H4 (4d), p-(CH3)(2)N-C6H4 (4e)) were obtained in moderate yields from reactions of C-60 with aldehydes 2a-e and N-methylglycine (Prato reaction). In all these solvent-free reactions, 4a was found to be formed besides 4b-e, indicating that fullerenes can react with N-substituted glycines in the absence of aldehyde to give fulleropyrrolidines. For this novel reaction, a possible reaction mechanism involving an electron transfer process has been proposed. Intrigued by this observation, the dependence of the yield on the reagent ratio for the reaction of C-60 with paraformaldehyde and/or N-methylglycine was examined to search the optimal conditions. The reaction of C-70 with paraformaldehyde and/or N-methylglycine under HSVM conditions was also studied and was found to give the positional isomers of [70]fulleropyrrolidines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Fullerene–fluorescein–anthracene hybrids: a model for artificial photosynthesis and solar energy conversion
  作者：Bingwen Jing、Daoben Zhu

  DOI：10.1016/j.tetlet.2003.10.136

  日期：2004.1

  Two novel C-60-fluorescein-anthracene hybrids have been synthesized. Fluorescence quenching in the hybrids indicates an energy transfer from the excited state of anthracene to fluorescein and photoinduced intramolecular electron transfer from the excited state of fluorescein to the C-60 moiety. (C) 2003 Elsevier Ltd. All rights reserved.
• Energy Transfer Processes in Novel Subphthalocyanine−Fullerene Ensembles
  作者：David González-Rodríguez、Tomás Torres、Dirk M. Guldi、José Rivera、Luis Echegoyen

  DOI：10.1021/ol0169022

  日期：2002.2.1

  [GRAPHICS]series of subphthalocyanine-C-60 dyads in which the two subunits are placed at different distances have been prepared and their electrochemical properties measured. Photophysical measurements reveal energy transfer events following the initial photoexcitation of the subphthalocyanine chromophore.