1,2-bis(4'-butoxybiphenyl-4-yl)ethane-1,2-dione | 1258434-21-7

• 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'-butoxybiphenyl-4-yl)ethane-1,2-dione
• 英文别名: 1,2-bis(4′-butoxybiphenyl-4-yl)ethane-1,2-dione；1,2-bis(4'-butoxy-1',4-biphen-1-yl)-ethanedione
• CAS: 1258434-21-7
• 化学式: C₃₄H₃₄O₄
• 分子量: 506.642
• InChiKey: HOVMWXXEYVZYPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(4'-butoxybiphenyl-4-yl)ethane-1,2-dione 、 4,8-di-2-thienylbenzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole 在 溶剂黄146 、 锌 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以32%的产率得到2,3,7,8-tetra(4'-butoxy-1',4-biphen-1-yl)-5,10-bis(thien-2-yl)pyrazino[2,3-g]quinoxaline
  参考文献：
  名称：

  通过选择性还原苯并[1,2- c ; 4,5- c ]合成低带隙[1,2,5]-噻二唑并[3,4- g ]喹喔啉和吡嗪并[2,3- g ]喹喔啉衍生物′]双[1,2,5]噻二唑

  摘要：

  可以有选择地进行二噻吩基苯并双噻二唑衍生物TBBT的还原反应，以提供[1,2,5]-噻二唑并[ 3,4- g ]喹喔啉（TQ）或吡嗪并[2,3- g ]喹喔啉（PQ）衍生物。 。与目前的方法相比，这种方法为PQ和TQ派生提供了更为温和，更短和更有效的途径。进一步显示了如何通过选择合适的取代基来调节PQ和TQ的光学和电化学性质。

  DOI：

  10.1021/ol102465a
• 作为产物：
  描述：

  4,4'-二溴联苯酰 、 4-丁氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 以84%的产率得到1,2-bis(4'-butoxybiphenyl-4-yl)ethane-1,2-dione
  参考文献：
  名称：

  通过选择性还原苯并[1,2- c ; 4,5- c ]合成低带隙[1,2,5]-噻二唑并[3,4- g ]喹喔啉和吡嗪并[2,3- g ]喹喔啉衍生物′]双[1,2,5]噻二唑

  摘要：

  可以有选择地进行二噻吩基苯并双噻二唑衍生物TBBT的还原反应，以提供[1,2,5]-噻二唑并[ 3,4- g ]喹喔啉（TQ）或吡嗪并[2,3- g ]喹喔啉（PQ）衍生物。 。与目前的方法相比，这种方法为PQ和TQ派生提供了更为温和，更短和更有效的途径。进一步显示了如何通过选择合适的取代基来调节PQ和TQ的光学和电化学性质。

  DOI：

  10.1021/ol102465a

文献信息

• Synthesis and Characterization of [1,2,5]Chalcogenazolo[3,4-f]benzo[1,2,3]triazole and [1,2,3]Triazolo[3,4-g]quinoxaline Derivatives
  作者：Teck Lip Tam、Hairong Li、Yeng Ming Lam、Subodh G. Mhaisalkar、Andrew C. Grimsdale

  DOI：10.1021/ol201829s

  日期：2011.9.2

  The synthesis and characterization is reported of low bandgap [1,2,5]chalcogenazolo[3,4-f]benzo[1,2,3]triazole and [1,2,3]triazolo[3,4-g]quinoxaline derivatives that display higher solubility and stability then their thiadiazole counterparts, [1,2,5]chalcogenazolo[3,4-f]benzo[2,1,3]thiadiazole and [1,2,5]thiadiazolo[3,4-g]quinoxaline, respectively.

  报道了低带隙的[1,2,5]硫族az唑[3,4-f]苯并[1,2,3]三唑和[1,2,3]三唑并[3,4-g]喹喔啉的合成与表征衍生物比噻二唑相应的衍生物具有更高的溶解度和稳定性，[1,2,5]硫代恶唑[3,4-f]苯并[2,1,3]噻二唑和[1,2,5]噻二唑[3,4- g]喹喔啉。
• Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules
  作者：Teck Lip Tam、Feng Zhou、Hairong Li、Jane Chieh Yu Pang、Yeng Ming Lam、Subodh G. Mhaisalkar、Haibin Su、Andrew C. Grimsdale

  DOI：10.1039/c1jm12347e

  日期：——

  We report the synthesis and characterization of pyrazino[2,3-g]quinoxaline derivatives with a systematic change in the substituents at the 2, 3, 7 and 8 positions and with or without 2-thienyl at the 5 and 10 positions to study the substituent effect and quinoid character of such a system. We performed density functional theory calculations using the B3LYP functional and 6-31G* basis set under the geometry optimization condition, together with the resonance effect of a valence bond theory to understand the electronic structures of these molecules. It was found that a combination of conjugation and cross-conjugation effects is responsible for the observed trends in their electronic properties, thus giving insights into designing molecules utilizing such effects.

  我们报告了吡嗪并[2,3-g]喹喔啉衍生物的合成和表征，这些衍生物在 2、3、7 和 8 位上的取代基发生了系统性变化，在 5 和 10 位上有或没有 2-噻吩基，从而研究了这种体系的取代基效应和喹啉特性。我们在几何优化条件下使用 B3LYP 函数和 6-31G* 基集进行了密度泛函理论计算，并利用价键理论的共振效应来了解这些分子的电子结构。结果发现，共轭效应和交叉共轭效应的结合是导致观察到的电子特性趋势的原因，从而为利用这种效应设计分子提供了启示。
• From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics
  作者：Teck Lip Dexter Tam、Teddy Salim、Hairong Li、Feng Zhou、Subodh G. Mhaisalkar、Haibin Su、Yeng Ming Lam、Andrew C. Grimsdale

  DOI：10.1039/c2jm33317a

  日期：——

  Here we report the syntheses of low bandgap polymers based on benzobisthiadiazole (BBT), thiadiazoloquinoxaline (TQ) and pyrazinoquinoxaline (PQ) core structures with different aromatic substituents. The effects of changing core structures from BBT to PQ and also substituents from biphenyl and bithienyl on the photophysical, electrochemical and morphology of the polymers were studied. These polymers were incorporated into solar cell devices as donors, with PC[71]BM as acceptors, and their device performances were correlated with their properties. It was found that the effect of these structural changes has significant consequences on the overall device performances.

  在此，我们报告了基于苯并双噻二唑（BBT）、噻二唑并喹喔啉（TQ）和吡嗪并喹喔啉（PQ）核心结构的不同芳香族取代基的低带隙聚合物的合成。研究了从BBT到PQ的核心结构变化以及从联苯和联噻吩到取代基的变化对聚合物的光物理、电化学和形态的影响。这些聚合物作为供体掺入太阳能电池器件中，PC[71]BM作为受体，其器件性能与其性质相关。研究发现，这些结构变化对器件的整体性能有重大影响。
• Synthesis and Characterization of a Series of Annelated Benzotriazole Based Polymers with Variable Bandgap
  作者：Teck Lip Dexter Tam、Wanting Ye、Hong Hup Ronnie Tan、Feng Zhou、Haibin Su、Subodh G. Mhaisalkar、Andrew C. Grimsdale

  DOI：10.1021/jo301281d

  日期：2012.11.16

  Here we report the synthesis and characterization of a series of annelated benzotriazole based polymers with variable bandgap. Benzobistriazole monomers reported by us previously were desymmetrized using partial reduction ring opening followed by ring closure to produce a wide range of annelated benzotriazole based monomers. These monomers were co-polymerized with a fluorene moiety to give polymers with bandgaps ranging from 1.16 to 2.41 eV.