1-(3-(Chlorocarbonyl)propyl)-1-phenyl<6.6>C61 | 161196-27-6

• 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-(3-(Chlorocarbonyl)propyl)-1-phenyl<6.6>C61
• 英文别名: [6,6]-phenyl-C₆₁-butyric acid chloride；(6,6)-phenyl C61 butyryl chloride；1-[3-(Chlorocarbonyl)propyl]-1-phenyl[6.6]C61
• CAS: 161196-27-6
• 化学式: C₇₁H₁₁ClO
• 分子量: 915.321
• InChiKey: JRBCXGHROPOHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  73
• 可旋转键数：
  5
• 环数：
  34.0
• 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：

  组胺 、 1-(3-(Chlorocarbonyl)propyl)-1-phenyl<6.6>C61 在 吡啶 作用下， 反应 18.0h， 以68%的产率得到1-(3-(ω-N-Histaminocarbonyl)propyl)-1-phenyl<6.6>C61
  参考文献：
  名称：

  Preparation and Characterization of Fulleroid and Methanofullerene Derivatives

  摘要：

  We describe the synthesis and complete characterization of soluble derivatives of C-60 for applications to physics and biology. The goal of the strategy was to have a ''modular'' approach in order to be able to easily vary a functional group attached indirectly to the cluster. The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy). The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes. An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques. This problem was solved by the use of MALDIMS. The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives. Both isomeric forms ([5,6], fulleroid and [6,6], methanofullerene) of the C-61 clusters were prepared. The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively. The fulleroid and methano-fullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.

  DOI：

  10.1021/jo00108a012
• 作为产物：
  描述：

  [6,6]-phenyl-C61-butyric acid 在 氯化亚砜 作用下， 以 二硫化碳 为溶剂， 反应 18.0h， 以88%的产率得到1-(3-(Chlorocarbonyl)propyl)-1-phenyl<6.6>C61
  参考文献：
  名称：

  Stabilization of the nanomorphology of polymer–fullerene “bulk heterojunction” blends using a novel polymerizable fullerene derivative

  摘要：

  通过使用可聚合富勒烯衍生物交联聚合物基体中的小分子相，可以实现用于体异质结太阳能电池的供体-受体共混物的形态稳定。在一项比较研究中，研究人员分别以聚（3-己基噻吩）（P3HT）为聚合物，以 C61-丁酸甲酯（PCBM）或新合成的可聚合富勒烯衍生物 C61-丁酸缩水甘油酯（PCBG）为受体分子，研究了聚合物与富勒烯混合物薄膜的形态。通过原子力显微镜（AFM）、透射电子显微镜（TEM）和光致发光（PL）研究，研究了薄膜热处理后的纳米形态变化。聚合过程通过红外线吸收研究进行了监测。这些比较研究表明，这种新合成的富勒烯能显著稳定这些混合物的固态形态。这种防止块状异质结形态长期高温不稳定的方法，为提高塑料太阳能电池在未来应用中的运行稳定性提供了一条重要途径。

  DOI：

  10.1039/b505361g

文献信息

• Surface-Segregated Monolayers: A New Type of Ordered Monolayer for Surface Modification of Organic Semiconductors
  作者：Qingshuo Wei、Keisuke Tajima、Yujin Tong、Shen Ye、Kazuhito Hashimoto

  DOI：10.1021/ja9057053

  日期：2009.12.9

  We report a new type of ordered monolayer for the surface modification of organic semiconductors. Fullerene derivatives with fluorocarbon chains ([6,6]-phenyl-C(61)-buryric acid 1H,1H-perfluoro-1-alkyl ester or FC(n)) spontaneously segregated as a monolayer on the surface of a [6,6]-phenyl-C(61)-butyric acid methyl ester (PCBM) film during a spin-coating process from the mixture solutions, as confirmed

  我们报告了一种用于有机半导体表面改性的新型有序单层。具有碳氟链的富勒烯衍生物（[6,6]-苯基-C（61）-伯里酸1H，1H-全氟-1-烷基酯或FC（n））自发地分离为[6， 6]-苯基-C(61)-丁酸甲酯 (PCBM) 薄膜在旋涂过程中从混合物溶液中得到，如 X 射线光电子能谱 (XPS) 所证实。紫外光电子能谱 (UPS) 显示电离电位 (IP) 的变化取决于碳氟化合物链的长度，表明表面偶极矩的形成。表面敏感振动光谱，和频生成 (SFG) 揭示了表面 FC(n) 层中 C(60) 部分的有序分子取向。当氟碳链的长度改变时，来自表面 FC(n) 的 SFG 信号的强度显示出明显的奇偶效应。这种表面分离单层的新概念为修饰有机半导体的表面提供了一种简便而通用的方法，适用于各种有机光电器件。
• Efficient charge generation and collection in organic solar cells based on low band gap dyad molecules
  作者：Seiichiro Izawa、Kazuhito Hashimoto、Keisuke Tajima

  DOI：10.1039/c1cc11387a

  日期：——

  Low band gap dyad molecules were prepared that have absorption spectra matched well with the solar spectrum, and the construction of efficient charge transport pathways was observed. Under AM 1.5 illumination, the devices have achieved the highest J(SC) (4.79 mA cm(2)) and FF (0.46) in dyad-based organic solar cells to date.

  制备了具有与太阳光谱良好匹配的吸收谱的低带隙二元分子，并观察到了有效的电荷传输路径的构建。迄今为止，在AM 1.5照明下，该器件已实现了基于二倍体的有机太阳能电池的最高J（SC）（4.79 mA cm（2））和FF（0.46）。
• Complementary Hydrogen Bonding and Block Copolymer Self-Assembly in Cooperation toward Stable Solar Cells with Tunable Morphologies
  作者：Fei Li、Kevin G. Yager、Noel M. Dawson、Jianzhong Yang、Kevin J. Malloy、Yang Qin

  DOI：10.1021/ma4016399

  日期：2013.11.26

  report the synthesis and characterization of a polythiophene diblock copolymer selectively functionalized with 1-n-hexylisoorotic acid moieties (P4) and a 2,6-diaminopyridine tethered fullerene derivative (PCBP). Self-assembly between P4 and PCBP through “three-point” complementary hydrogen bonding interactions is utilized to control and stabilize blend morphologies. These interactions have been studied

  我们报告的合成和表征的聚噻吩二嵌段共聚物选择性地功能化的1- n-己基异山梨酸部分（P4）和2,6-二氨基吡啶系留的富勒烯衍生物（PCBP）。通过“三点”互补氢键相互作用，P4和PCBP之间的自组装可用于控制和稳定共混物形态。通过1 H NMR和UV-vis光谱以及光学和原子力显微镜（AFM）研究了溶液和固态中的这些相互作用。采用P4的太阳能电池混合并测试了不同重量比的PCBP和苯基-C61-丁酸甲酯（PCBM）。在由P4 / PCBP混合物（10/8重量）和P4 / PCBP / PCBM三元混合物（10/4/4重量）作为活性层制成的器件中观察到了最佳的功率转换效率（PCE）。通过老化测试详细研究了这些太阳能电池的热稳定性，并通过吸收光谱，光学显微镜，AFM和X射线分析密切监测了相应的形态变化。P4之间的“三点”互补氢键相互作用与PCBP结合嵌段聚合物自组装，发现不仅可以显着提高太阳能电
• Efficiency enhancement of P3HT/PCBM bulk heterojunction solar cells by attaching zinc phthalocyanine to the chain-end of P3HT
  作者：Jea Uk Lee、Young Do Kim、Jea Woong Jo、Jae Pil Kim、Won Ho Jo

  DOI：10.1039/c1jm11563d

  日期：——

  A new solution processable zinc phthalocyanine dye (ZnPc), as an interface modifier between poly(3-hexylthiophene) (P3HT) and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) in bulk heterojunction solar cells, was successively synthesized and linked to the chain-end of P3HT through the formation of a coordination complex. ZnPc dye molecules do not aggregate but preferentially locate at the interface between P3HT and PCBM, and thus contribute to the photocurrent generation by both direct photo-excitation and enhancement of charge transfer between P3HT and PCBM. To localize the zinc phthalocyanine dyes at the donor–acceptor interface more effectively, another new organic dye molecule, fullerene-functionalized zinc phthalocyanine (ZnPc-C60) was also synthesized and linked to the chain-end of the P3HT, where ZnPc-C60 contributes not only to the photocurrent generation by direct photo-excitation, but also lowers the interfacial tension, resulting in the reduction of the domain size and the suppression of the macrophase separation of the P3HT/PCBM blend for prolonged thermal annealing. This leads to higher device efficiency with 20% enhancement of the short circuit current and to enhancement of long-term thermal stability of device performance as compared to that of the reference P3HT/PCBM device.

  一种新的可溶液加工的锌酞菁染料（ZnPC）被成功合成，并通过形成配位复合物与 P3HT 的链端相连，作为体异质结太阳能电池中聚（3-己基噻吩）（P3HT）与 [6,6]- 苯基-C61-丁酸甲酯（PCBM）之间的界面修饰剂。ZnPC 染料分子不会聚集，而是优先位于 P3HT 和 PCBM 之间的界面上，从而通过直接光激发和增强 P3HT 与 PCBM 之间的电荷转移来促进光电流的产生。为了更有效地将酞菁锌染料定位于供体-受体界面，还合成了另一种新的有机染料分子--富勒烯功能化酞菁锌（ZnPC-C60），并将其连接到 P3HT 的链端、其中，ZnPC-C60 不仅有助于通过直接光激发产生光电流，还能降低界面张力，从而减小 P3HT/PCBM 共混物的畴尺寸并抑制其在长时间热退火后的大相分离。因此，与参考 P3HT/PCBM 器件相比，器件效率更高，短路电流增加了 20%，器件性能的长期热稳定性也得到了提高。
• Efficient dyad-based organic solar cells with a highly crystalline donor group
  作者：Takeshi Nishizawa、Hady Kesuma Lim、Keisuke Tajima、Kazuhito Hashimoto

  DOI：10.1039/b902060h

  日期：——

  A novel oligo(p-phenylenevinylene)(OPV)-fullerene dyad, with strong intermolecular π–π interactions between the donor groups, led to improvements in the fill factor and power conversion efficiency of dyad-based solar cells of up to 0.44 and 1.28%, respectively, which are the highest values reported for dyad-based solar cells to date.

  一种新型寡（对苯基乙烯）（OPV）-富勒烯二聚体，在供体基团之间具有强烈的分子间π-π相互作用，使基于二聚体的太阳能电池的填充因子和功率转换效率分别提高了0.44%和1.28%，这是迄今为止基于二聚体的太阳能电池的最高值。