4,4'-dihexyloxybenzophenone p-tosylhydrazone | 1108157-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-dihexyloxybenzophenone p-tosylhydrazone
• 英文别名: N-[bis(4-hexoxyphenyl)methylideneamino]-4-methylbenzenesulfonamide
• CAS: 1108157-35-2
• 化学式: C₃₂H₄₂N₂O₄S
• 分子量: 550.762
• InChiKey: BSTQGEOBBBMRLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-dihexyloxybenzophenone p-tosylhydrazone 在 sodium methylate 作用下， 以 吡啶 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Synthesis of a π-conjugated oligomer–fullerene dyad through a versatile [6,6]diphenylmethanofullerene carboxylic acid

  摘要：

  In this article we describe the synthesis of an electron donor-acceptor dyad containing a [6,6]diphenylmethanofullerene moiety as the electron acceptor and a dialkylamino-substituted oligo-p-phenyl-enevinylene as the electron donor. The synthesis of this material has been successfully accomplished by an esterification reaction between a [6,6]diphenylmethanofullerene functionalized with a carboxylic acid and the corresponding oligomer substituted with a benzyl alcohol. Cyclic voltammetry and absorption spectroscopy show that both electroactive units preserve their nature in the ground state, whereas preliminary photophysical investigations show a strong fluorescence quenching. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.077
• 作为产物：
  描述：

  4,4'-双(己氧基苯基)甲酮 、 对甲苯磺酰肼 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以82%的产率得到4,4'-dihexyloxybenzophenone p-tosylhydrazone
  参考文献：
  名称：

  Polymer solar cells based on diphenylmethanofullerenes with reduced sidechain length

  摘要：

  二苯基甲烷富勒烯（DPMs）作为聚合物体异质结太阳能电池的受体显示出有趣的特性，因为与它们的能量水平相比，它们能产生很高的开路电压。在此，我们研究了将 DPM 的烷烃侧链长度从 C12 减少到 C6 对太阳能电池性能的影响。这一变化导致电子迁移率增加，从而使富勒烯含量降低，进而导致短路电流增加，最后，由于薄膜中吸收性更强的聚合物浓度提高，设备效率也随之提高（从 2.3% 提高到 2.6%）。原子力显微镜图像和外部量子效率表明，与标准富勒烯[6,6]-苯基-C61-丁酸甲酯相比，DPM 的性能略有下降的原因在于富勒烯没有结晶，这意味着使用这类富勒烯可以实现更高的效率。

  DOI：

  10.1039/c0jm01160f

文献信息

• Efficient microwave-mediated synthesis of fullerene acceptors for organic photovoltaics
  作者：Vincenzo Campisciano、Serena Riela、Renato Noto、Michelangelo Gruttadauria、Francesco Giacalone

  DOI：10.1039/c4ra10495a

  日期：——

  Two different processes, namely the Bamford–Stevens and [4 + 2] Diels Alder reactions, have been optimized under microwave irradiation for the functionalization of fullerenes. In this manner, all the main C60- and C70-based acceptor derivatives for organic solar cells such as PCBM, DPM, BHN and ICBA, have been prepared in higher yields and shorter reaction times with respect to the reported data. These findings represent a step forward toward the wide production of cheaper organic solar cells as a consequence of the cost abatement of the acceptors given by higher yields, lower waste production, and reduced reaction time which means a strong energy saving.

  在微波辐照下优化了富勒烯功能化的两种不同过程，即 Bamford-Stevens 反应和 [4 + 2] Diels Alder 反应。通过这种方式，制备出了用于有机太阳能电池的所有基于 C60 和 C70 的主要受体衍生物，如 PCBM、DPM、BHN 和 ICBA，与报告数据相比，产率更高、反应时间更短。这些发现标志着向广泛生产更廉价的有机太阳能电池迈进了一步，因为更高的产量、更低的废物产生量和更短的反应时间降低了受体的成本，这意味着极大地节约了能源。
• Synthesis of a π-conjugated oligomer–fullerene dyad through a versatile [6,6]diphenylmethanofullerene carboxylic acid
  作者：Rafael Gómez、José L. Segura

  DOI：10.1016/j.tet.2008.10.077

  日期：2009.1

  In this article we describe the synthesis of an electron donor-acceptor dyad containing a [6,6]diphenylmethanofullerene moiety as the electron acceptor and a dialkylamino-substituted oligo-p-phenyl-enevinylene as the electron donor. The synthesis of this material has been successfully accomplished by an esterification reaction between a [6,6]diphenylmethanofullerene functionalized with a carboxylic acid and the corresponding oligomer substituted with a benzyl alcohol. Cyclic voltammetry and absorption spectroscopy show that both electroactive units preserve their nature in the ground state, whereas preliminary photophysical investigations show a strong fluorescence quenching. (C) 2008 Elsevier Ltd. All rights reserved.
• Polymer solar cells based on diphenylmethanofullerenes with reduced sidechain length
  作者：Henk J. Bolink、Eugenio Coronado、Alicia Forment-Aliaga、Martijn Lenes、Andrea La Rosa、Salvatore Filippone、Nazario Martín

  DOI：10.1039/c0jm01160f

  日期：——

  Diphenylmethanofullerenes (DPMs) show interesting properties as acceptors in polymer bulk heterojunction solar cells due to the high open circuit voltages they generate compared to their energy levels. Here we investigate the effect of reducing the alkane sidechain length of the DPMs from C12 to C6 in the properties of the solar cell. This change leads to an increase in the electron mobility, thus allowing for a lower fullerene content, which in turn results in an increase in the short circuit current and, finally, in an increase in the efficiency of the device (from 2.3 to 2.6%) due to the higher concentration of the more absorbing polymer in the film. Atomic force microscopy images and external quantum efficiencies suggest the absence of crystallization of the fullerene to be at the origin of the slightly reduced performance of DPMs versus the standard fullerene [6,6]-phenyl-C61-butyric acid methyl ester, implying that higher efficiencies could be possible with this class of fullerenes.

  二苯基甲烷富勒烯（DPMs）作为聚合物体异质结太阳能电池的受体显示出有趣的特性，因为与它们的能量水平相比，它们能产生很高的开路电压。在此，我们研究了将 DPM 的烷烃侧链长度从 C12 减少到 C6 对太阳能电池性能的影响。这一变化导致电子迁移率增加，从而使富勒烯含量降低，进而导致短路电流增加，最后，由于薄膜中吸收性更强的聚合物浓度提高，设备效率也随之提高（从 2.3% 提高到 2.6%）。原子力显微镜图像和外部量子效率表明，与标准富勒烯[6,6]-苯基-C61-丁酸甲酯相比，DPM 的性能略有下降的原因在于富勒烯没有结晶，这意味着使用这类富勒烯可以实现更高的效率。