1,2-(4'-oxacyclohexano)[60]fullerene | 150304-28-2

• 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: 1,2-(4'-oxacyclohexano)[60]fullerene
• 英文别名: 1,2-(4'-oxocyclohexano)fullerene；1,2-(4’-oxocyclohexano)[60]fullerene
• CAS: 150304-28-2
• 化学式: C₆₄H₆O
• 分子量: 790.751
• InChiKey: ATJRJBFLNUHWGX-UHFFFAOYSA-N

物化性质

• 密度：
  2.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  65
• 可旋转键数：
  0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-(4'-oxacyclohexano)[60]fullerene 以 邻二氯苯 为溶剂， 反应 12.0h， 生成 足球烯
  参考文献：
  名称：

  用于有机太阳能电池的新型高效（硫代）缩醛化富勒烯单加合物：基于溶解度，迁移率平衡和暗电流的表征†

  摘要：

  我们报告了使用新型螺缩醛化和（硫代）缩醛化[60]富勒烯单加合物带有五至七元环的有机光伏电池的系统研究。这些化合物之一的PTB7的功率转换效率为5.8％，而聚（3-己基噻吩）的功率转换效率为4.0％。后者与常用的[6,6]-苯基-C 61-丁酸甲酯相当。我们通过检查溶解度，空穴和电子的空间电荷限制电流迁移率平衡，形态和暗电流来研究控制器件性能的精确因素。单晶X射线衍射凸显了富勒烯填料边缘空间中紧凑而灵活的螺环折叠的关键作用。

  DOI：

  10.1039/c4ta05965d
• 作为产物：
  描述：

  1,2-(1’,5’-dioxaspiro[5.5]-8’,9’-undecano)[60]fullerene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以95%的产率得到1,2-(4'-oxacyclohexano)[60]fullerene
  参考文献：
  名称：

  Synthesis and characterization of new acetalized [60]fullerenes

  摘要：

  Acetalized [60]fullerenes were synthesized from cyclohexanone-fused [60]fullerene, which was facilely prepared by Diels-Alder reaction of C-60 with silylether diene, on treatment of various aliphatic alcohols under TiCl4 catalyst. The spiro-cyclic acetalized [60]fullerenes having five, six, and seven-membered rings were also synthesized by using the corresponding diols under the same condition. The slightly raised reduction potentials E-red (similar to 0.04 V) relative to those of PCBM were observed by cyclic voltammetry measurement, depending on the identity of alkyl group/chain. The noncyclic acetalized [60]fullerenes showed lower thermal stability up to 200 degrees C, while the cyclic ones exhibited the drastically improved thermal stability up to 350 degrees C under nitrogen atmosphere. The acid-catalyzed hydrolysis easily removed the acetal moiety quantitatively, resulting in a considerable change of solvent solubility of the fullerene. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.093

文献信息

• Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivative·gamma-cyclodextrin complexes
  作者：Atsushi Ikeda、Akiko Hirata、Michiko Ishikawa、Jun-ichi Kikuchi、Shunsuke Mieda、Wataru Shinoda

  DOI：10.1039/c3ob41513a

  日期：——

  We have demonstrated that C60 derivatives bearing a pyrrolidine moiety as well as a variety of other substituents can form 1 : 2 complexes with γ-cyclodextrin (γ-CDx) using a mechanochemical high-speed vibration milling apparatus. When the influence of the steric hindrance of the substituents on the formation of the complexes was negligible, the water-solubilities of the complexes were shown experimentally to be completely dependent on the hydrophobic properties of the substituent. Furthermore, the stabilities of the γ-CDx-complexes of several different C60 derivatives were found to be similar to or slightly higher than that of the C60·γ-CDx complex, with the solubilities of the complexes showing no correlation to the stabilities. Based on the results of a series of theoretical investigations, we have shown that the stabilities of the γ-CDx-complexes can be affected not only by steric effects but also by the polarities of the substituent groups, which exist in the vicinity of the upper rim of γ-CDx, because the water bound to the polar group can assist in the stabilisation of the complexes.

  我们利用机械化学高速振动研磨装置证明，含有吡咯烷分子以及其他多种取代基的 C60 衍生物可以与δ³-环糊精（δ³-CDx）形成 1:◎2 复合物。当取代基的立体阻碍对络合物形成的影响可以忽略不计时，实验证明络合物的水溶性完全取决于取代基的疏水性。此外，研究还发现几种不同 C60 衍生物的 δ³-CDx 复合物的稳定性与 C60Â-δ³-CDx 复合物的稳定性相似或略高于后者，而复合物的溶解度与稳定性没有相关性。根据一系列理论研究的结果，我们发现 δ³-CDx 复合物的稳定性不仅会受到立体效应的影响，还会受到存在于 δ³-CDx 上缘附近的取代基团极性的影响，因为与极性基团结合的水可以帮助稳定复合物。
• Fullerene-Derivatized Amino Acids: Synthesis, Characterization, Antioxidant Properties, and Solid-Phase Peptide Synthesis
  作者：Jianzhong Yang、Lawrence B. Alemany、Jonathan Driver、Jeffrey D. Hartgerink、Andrew R. Barron

  DOI：10.1002/chem.200601186

  日期：2007.3.16

  appropriately protected (4-amino)phenylalanine and lysine, respectively. Conversion of the imine to the corresponding amine is achieved by di-acid catalyzed hydroboration. The reduction of the imine is not accompanied by hydroboration of the fullerene cage. The [70]fullerene phenylalanine derivative has also been prepared as have the di-amino acid derivatives. The compounds were characterized by MALDI-TOF mass

  一系列的[60]富勒烯取代的苯丙氨酸（Baa）和赖氨酸衍生物是通过将1,2-（4'-氧代环己基）富勒烯分别与适当保护的（4-氨基）苯丙氨酸和赖氨酸缩合制备的。通过二酸催化的硼氢化反应可将亚胺转化为相应的胺。亚胺的还原不伴随富勒烯笼的硼氢化。还已经制备了[70]富勒烯苯丙氨酸衍生物，以及二氨基酸衍生物。通过MALDI-TOF质谱，UV / Vis光谱和循环伏安法对化合物进行表征。1H和13C NMR光谱可观察到非对映异构体。富勒烯取代的肽可以通过固相肽合成以较大规模合成。与天然肽相比，肽中C60取代的氨基酸的存在对肽的二级结构和自组装特性具有显着影响。Baa和Baa衍生的阴离子肽的抗氧化剂测定比Trolox显着更有效。
• [EN] PROCESS AND METHOD FOR THE EFFICIENT PREPARATION OF FULLERYNES<br/>[FR] PROCÉDÉ ET MÉTHODE POUR LA PRÉPARATION EFFICACE DE FULLERYNES
  申请人：UNIV AKRON

  公开号：WO2012005762A1

  公开（公告）日：2012-01-12

  The preparation of novel fullerynes which are fullerenes (e.g. C60, C70, C80, etc.) that contain one or more alkyne functionalities and may contain additional functional groups such as hydroxyls, halogens, esters, haloesters, phenyl, oligo(ethylene glycol)s, perfluorinated alkyl chains, and the like. Two desired preparation routes are disclosed. The first one is the Fischer esterification in desired solvents using a special designed reactor in contrast to the heretofore initial Steglich reaction that results in side reactions and low yields. The second one uses acetylide Grignard reagents that have reduced nucleophilicity and higher stability in contrast to the use of heretofore initial lithium organyls or other Grignard reagents that would add to C60 with possible multi-additions in an uncontrollable manner.

  制备新型富勒烯，该富勒烯（例如C60，C70，C80等）含有一个或多个炔基官能团，并可能含有额外的官能团，例如羟基，卤素，酯，卤代酯，苯基，寡聚（乙二醇）和全氟烷基等。文中介绍了两种所需的制备路线。第一种是在特定溶剂中使用特殊设计的反应器进行Fischer酯化反应，与此前的Steglich反应相比，可以避免副反应和低收率。第二种方法使用乙炔基格氏试剂，其亲核性降低且稳定性更高，相比于此前使用的锂有机化合物或其他格氏试剂，可以避免多次无法控制的加成反应。
• Sequential "Bis-Michael" Additions of Dienolates with C60: Rapid Access to Sterically Congested Buckminsterfullerene Derivatives with Defined Stereochemistry
  作者：Padma S. Ganapathi、Yves Rubin

  DOI：10.1021/jo00115a002

  日期：1995.5
• Toward Controlled Spacing in One-Dimensional Molecular Chains:  Alkyl-Chain-Functionalized Fullerenes in Carbon Nanotubes
  作者：Thomas W. Chamberlain、Andrew Camenisch、Neil R. Champness、G. Andrew D. Briggs、Simon C. Benjamin、Arzhang Ardavan、Andrei N. Khlobystov

  DOI：10.1021/ja071803q

  日期：2007.7.1

  A range of fullerenes (C-60) functionalized with long alkyl chains have been synthesized and inserted into single-walled carbon nanotubes. The impact of the alkyl chain length and of the type of linker between the addend and the fullerene cage on the geometry of molecular arrays in nanotube has been studied by high-resolution transmission electron microscopy. In the presence of functional groups the mean interfullerene separations are significantly increased by 2-8 nm depending on the length of the alkyl chain, but the periodicity of the fullerene arrays is disrupted due to the conformational flexibility of the alkyl groups.