1,2-bis(4-(3,7-dimethyloctyloxy)phenyl)ethane-1,2-dione | 916841-12-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(4-(3,7-dimethyloctyloxy)phenyl)ethane-1,2-dione
• 英文别名: 4,4'-bis(3,7-dimethyloctyloxy)benzil；4,4'-di(3,7-dimethyloctyloxy)benzil；1,2-Bis[4-(3,7-dimethyloctoxy)phenyl]ethane-1,2-dione；1,2-bis[4-(3,7-dimethyloctoxy)phenyl]ethane-1,2-dione
• CAS: 916841-12-8
• 化学式: C₃₄H₅₀O₄
• 分子量: 522.769
• InChiKey: PPSBDSQXWWRBQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-(3,7-dimethyloctyloxy)phenyl)ethane-1,2-dione 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 31.33h， 生成 2,3-bis(4-(3,7-dimethyloctyloxy)phenyl)-5,8-bis(5'-bromodithien-2-yl)quinoxaline
  参考文献：
  名称：

  Synthesis and Photovoltaic Properties of Quinoxaline-Based Alternating Copolymers for High-Efficiency Bulk-Heterojunction Polymer Solar Cells

  摘要：

  A series of quinoxaline-based copolymers, namely, poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-quinoxaline)] (P1), poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5- (5',8'-di-2-thienyl-2,3-bis (4-octyloxyl)phenyl)quinoxaline] (P2), and poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-2,3-bis(4-(3,7-dimethyloctyloxy)pheny)quinoxaline] (P3), were synthesized and characterized for use in polymer solar cells (PSCs). We describe the effect of modifying the alkyl group of the side chain of the quinoxaline derivatives on the electronic and optoelectronic properties of the polymers. The field-effect hole mobility as well as the electronic energy levels and processability of the materials for PSC applications were investigated. Among the studied quinoxaline-based copolymers, P2 showed the best photovoltaic performance with an open-circuit voltage (V(OC)) of 0.82 V, a short-circuit current density (J(SC)) of 9.96 mA/cm(2), a fill. factor (FF) of 0.49, and a power-conversion efficiency of 4.0% when a P2/PC(71)BM blend film was used as the active layer under AM 1.5 G irradiation (100 mW/cm(2)).

  DOI：

  10.1021/ma102943g
• 作为产物：
  描述：

  4-溴苯酚 在 正丁基锂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 1,2-bis(4-(3,7-dimethyloctyloxy)phenyl)ethane-1,2-dione
  参考文献：
  名称：

  Synthesis and Photovoltaic Properties of Quinoxaline-Based Alternating Copolymers for High-Efficiency Bulk-Heterojunction Polymer Solar Cells

  摘要：

  A series of quinoxaline-based copolymers, namely, poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-quinoxaline)] (P1), poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5- (5',8'-di-2-thienyl-2,3-bis (4-octyloxyl)phenyl)quinoxaline] (P2), and poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-2,3-bis(4-(3,7-dimethyloctyloxy)pheny)quinoxaline] (P3), were synthesized and characterized for use in polymer solar cells (PSCs). We describe the effect of modifying the alkyl group of the side chain of the quinoxaline derivatives on the electronic and optoelectronic properties of the polymers. The field-effect hole mobility as well as the electronic energy levels and processability of the materials for PSC applications were investigated. Among the studied quinoxaline-based copolymers, P2 showed the best photovoltaic performance with an open-circuit voltage (V(OC)) of 0.82 V, a short-circuit current density (J(SC)) of 9.96 mA/cm(2), a fill. factor (FF) of 0.49, and a power-conversion efficiency of 4.0% when a P2/PC(71)BM blend film was used as the active layer under AM 1.5 G irradiation (100 mW/cm(2)).

  DOI：

  10.1021/ma102943g

文献信息

• Synthesis and preliminary physical properties of new neutral tetraalkoxy-substituted nickel bis(1,2-dithiolene) complexes
  作者：Thanh-Tuan Bui、Bénédicte Garreau-de Bonneval、Kathleen I. Moineau-Chane Ching

  DOI：10.1039/b9nj00519f

  日期：——

  region. Electrochemical and optical properties of [Ni(dpedt)2] depend strongly on the nickel bis(1,2-dithiolene) core and very slightly on the alkyl chain lengths or configurations. These highly soluble coordination compounds are potential candidates as acceptor solution-processable materials for active layers in organic electronic devices, such as field effect transistors or photovoltaic devices.

  十九个中立 双二苯基乙二炔镍镍 配合物[镍（钯）2合成了包括17种新化合物在内的[]化合物，并通过一种新的短，有效和多克级合成方法进行了表征。初步的物理研究表明，这些络合物是吸电子材料，在近红外光谱区具有良好的热稳定性和较高的分子吸收系数。的电化学和光学性质[Ni（dpedt）2 ]在很大程度上取决于双（1,2-二硫代镍）镍的核心，而对烷基链的长度或构型的依赖则很小。这些高度可溶的配位化合物是潜在的候选物，可以用作有机电子器件（例如场效应晶体管或光伏器件）中有源层的受体溶液可处理材料。
• Long-range self-assembly of bis(imidazole)-annulated terphenyls
  作者：Wojciech Pisula、Frank Dierschke、Klaus Müllen

  DOI：10.1039/b608593h

  日期：——

  In our study, we present the synthesis and characterisation of the first bis(imidazole)-annulated terphenyl disc-shaped molecules, which self-organise into columnar structures throughout long-range ordered domains during cooling from the isotropic phase. Two derivatives substituted with 3,7-dimethyloctyl and 2-decyltetradecyl substituents have been prepared. Concentration dependent UV/vis investigations indicated pronounced aggregation of both compounds in solution. The structural analysis of mechanically aligned samples revealed columnar supramolecular order with favoured helical stacking of the discs with a pitch of four molecules independent of the substituents. On the other hand, significant differences in the self-organisation during solidification from the isotropic phase were observed. The bulkier the alkyl side chains, the lower the growth rate and the higher the macroscopic order of the domains. These novel bis(imidazole)-annulated terphenyls are promising candidates for field-effect transistor applications because of the pronounced molecular packing and the formation of macroscopically aligned domains with edge-on arranged molecules.

  在我们的研究中，我们报道了首例双(咪唑)并联三联苯盘状分子的合成与表征。这些分子在从各向同性相冷却过程中可以自组装成具有长程有序结构的柱状结构。我们制备了两种衍生物，分别取代基为3,7-二甲基辛基和2-癸基十四烷基。浓度依赖的紫外-可见光谱研究表明这两种化合物在溶液中都表现出明显的聚集行为。对机械取向样品的结构分析显示，不论取代基如何，分子都呈现柱状超分子有序排列，倾向于形成每四个分子为一个周期的螺旋堆叠结构。另一方面，在从各向同性相凝固过程中观察到明显不同的自组装行为。烷基侧链越大，生长速率越慢，且形成的宏观有序结构区域越大。由于这些新型双(咪唑)并联三联苯分子具有显著的分子堆积特性，且能形成边缘取向排列的宏观有序结构区域，因此它们是很有前途的场效应晶体管应用候选材料。