3'-methyl-1'-(4-nitrophenyl)pyrazolino[60]fullerene | 690255-10-8

• 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: 3'-methyl-1'-(4-nitrophenyl)pyrazolino[60]fullerene
• CAS: 690255-10-8
• 化学式: C₆₈H₇N₃O₂
• 分子量: 897.822
• InChiKey: DETPBUMDXCTSIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  73
• 可旋转键数：
  1
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-methyl-1'-(4-nitrophenyl)pyrazolino[60]fullerene 在 三氟甲磺酸酐 、 四甲基硝酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到
  参考文献：
  名称：

  Nitration of Fullerene Derivatives under Mild Conditions

  摘要：

  一种新的N-(2,4-二硝基苯基)-2-吡唑啉[60]富勒烯衍生物已通过使用三氟甲苯基氮离子进行电亲核硝化合成。CV和OSWV实验表明，与C60相比，这些物质显示出增强的电子受体特性（高达90 mV）。

  DOI：

  10.1055/s-2007-977425
• 作为产物：
  描述：

  acetaldehyde 4-nitrophenylhydrazone 、 足球烯 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 0.67h， 以42%的产率得到3'-methyl-1'-(4-nitrophenyl)pyrazolino[60]fullerene
  参考文献：
  名称：

  The Isoindazole Nucleus as a Donor in Fullerene-Based Dyads. Evidence for Electron Transfer

  摘要：

  A series of isoindazole-C-60 dyads 4a-c based on pyrazolino[60]fullerene have been prepared by 1,3-dipolar cycloadditions of the nitrile imines, generated in situ from hydrazones 3a-c, to C-60. Molecular orbital calculations for 4b revealed that the electron distribution of the HOMO is located on the isoindazole moiety, while the electron distribution of the LUMO is located on the C-60 moiety. Electrochemical properties of the new dyads 4a-c show a similar electron affinity with respect to C-60. Charge-transfer interactions in the ground state between the isoindazole ring and the fullerene cage are predicted by the molecular orbital calculations and confirmed by electrochemical studies in 4a,b. Steady-state fluorescence emission spectra of dyads 4a-c show that fluorescence intensities in polar benzonitrile solvent decrease with increasing electron-donating ability of the substituent attached on the isoindazole group. This was confirmed by the shortening of fluorescence lifetimes, from which intramolecular charge-separation rates and efficiencies via the excited singlet states of the fullerene moiety were evaluated. The yields of the triplet states in polar solvent decrease with the electron-donating ability, supporting the competitive formation of the charge-separated state with the intersystem crossing from the excited states. Thus, isoindazole[60]fullerene 4b can be considered a molecular switch with an AND logic gate.

  DOI：

  10.1021/jo0499017

文献信息

• On the Thermal Stability of [60]Fullerene Cycloadducts:  Retro-Cycloaddition Reaction of 2-Pyrazolino[4,5:1,2][60]fullerenes
  作者：Juan Luis Delgado、Frédéric Oswald、François Cardinali、Fernando Langa、Nazario Martín

  DOI：10.1021/jo702741n

  日期：2008.4.1

  2-Pyrazolino[4,5:1,2][60]fullerenes undergo a thermally induced retro-cycloaddition process whose efficiency is influenced by the nature of the C-substituent. C-Aryl-N-Aryl-2-pyrazolino[60]fullerenes (2a−d) poorly undergo a thermal retro-cycloaddition reaction even in the presence of a strong dipolarophile or a metal Lewis acid which, in contrast to other fullerene derivatives, shows their remarkable

  2-吡唑啉代[4,5：1,2] [60]富勒烯经历热诱导的逆环加成过程，其效率受C取代基的性质影响。C-芳基-N-芳基-2-吡唑啉基[60]富勒烯（2a - d）即使在强双极性亲和剂或金属路易斯酸（与其他富勒烯衍生物相比，显示出其卓越的热稳定性。C-烷基-N-芳基-2-吡唑啉[60]富勒烯（2e - f）表现出不同的行为，更容易受到三氟甲磺酸铜的影响，并导致高收率的逆环加成产物（原始C 60）。
• Oxidation of 3-Alkyl-Substituted 2-Pyrazolino[60]fullerenes: A New Formyl-Containing Building Block for Fullerene Chemistry
  作者：Juan Luis Delgado、François Cardinali、Eva Espíldora、M. Rosario Torres、Fernando Langa、Nazario Martín

  DOI：10.1021/ol801308g

  日期：2008.9.1

  A new building block for fullerene chemistry, endowed with a formyl group on C-3 of the 2-pyrazoline ring, has been prepared in a simple two-step synthesis by oxidation of readily available 3-alkyl-substituted 2-pyrazolino[60]fullerenes; the new building block paves the way for the preparation of new light-harvesting fullerenes.

  通过氧化现成的3-烷基取代的2-吡唑啉基，可以通过简单的两步合成法制备一种在2-吡唑啉环的C-3上带有甲酰基的富勒烯化学新结构[60]。富勒烯; 新的结构单元为制备新的集光富勒烯铺平了道路。