1,4-bis(3-methyl-2-thienyl)-2,5-bis(2-thienyl)benzene | 1049822-44-7

• 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: 1,4-bis(3-methyl-2-thienyl)-2,5-bis(2-thienyl)benzene
• 英文别名: 3-Methyl-2-[4-(3-methylthiophen-2-yl)-2,5-dithiophen-2-ylphenyl]thiophene
• CAS: 1049822-44-7
• 化学式: C₂₄H₁₈S₄
• 分子量: 434.671
• InChiKey: YQRYGLJZAZNZCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(3-methyl-2-thienyl)-2,5-bis(2-thienyl)benzene 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 168.0h， 以96%的产率得到1,4-bis(5-bromo-2-thienyl)-2,5-bis(3-methyl-2-thienyl)benzene
  参考文献：
  名称：

  Organic Halogenation Chemistry as a Vital Tool for the Construction of Functional π-Conjugated Materials

  摘要：

  最近和当前Tovar研究小组在利用有机卤化化学开发复杂有机电子材料方面的努力得到了描述。本文介绍了涉及自由基和电亲核反应途径的标准合成方法，以及利用可离子化质子或三氮烯作为芳香卤化物的掩蔽基团的策略。还讨论了前向合成过程，这些过程突出了可以应用于这些卤化底物以生成复杂的π-共轭分子的拓展化学。所提供的实例特定于该小组实验室的工作，但卤化程序足够通用，适用于许多其他共轭框架的应用。

  DOI：

  10.1055/s-0030-1260086
• 作为产物：
  描述：

  3-甲基-2-(三丁基锡)噻吩 、 1,4-bis(2-thienyl)-2,5-dibromobenzene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以61%的产率得到1,4-bis(3-methyl-2-thienyl)-2,5-bis(2-thienyl)benzene
  参考文献：
  名称：

  Conformation as a Protecting Group: A Regioselective Aromatic Bromination En Route to Complex π-Electron Systems

  摘要：

  A new strategy to achieve regioselective functionalization of a sterically congested aromatic system driven by conformational demands is described. Electrophilic substitution occurs at the more planarizable subunit without undesired chemistry at mutually reactive sites and without the need for protecting or masking groups that must be manipulated later. Model studies are described to understand this selectivity, and possibilities for the construction of orthogonal, differentially substituted pi-systems of relevance for molecular electronics are demonstrated.

  DOI：

  10.1021/ol801828n

文献信息

• Conformation as a Protecting Group: A Regioselective Aromatic Bromination En Route to Complex π-Electron Systems
  作者：Daryl A. Guthrie、John D. Tovar

  DOI：10.1021/ol801828n

  日期：2008.10.2

  A new strategy to achieve regioselective functionalization of a sterically congested aromatic system driven by conformational demands is described. Electrophilic substitution occurs at the more planarizable subunit without undesired chemistry at mutually reactive sites and without the need for protecting or masking groups that must be manipulated later. Model studies are described to understand this selectivity, and possibilities for the construction of orthogonal, differentially substituted pi-systems of relevance for molecular electronics are demonstrated.
• Organic Halogenation Chemistry as a Vital Tool for the Construction of Functional π-Conjugated Materials
  作者：John Tovar

  DOI：10.1055/s-0030-1260086

  日期：2011.8

  Recent and ongoing efforts by the Tovar research group to exploit organic halogenation chemistry for the development of complex organic electronic materials are described. Standard synthetic approaches involving free-radical and electrophilic reaction pathways are presented along with strategies that use ionizable protons or triazenes as masking groups for aromatic halides. Forward synthetic processes that highlight the extended chemistry that can be applied to these halogenated substrates to give complex π-conjugated molecules are also discussed. The examples presented are specific to work from the group’s laboratories, but the halogenation procedures are sufficiently general to be suitable for use on many other conjugated frameworks.

  最近和当前Tovar研究小组在利用有机卤化化学开发复杂有机电子材料方面的努力得到了描述。本文介绍了涉及自由基和电亲核反应途径的标准合成方法，以及利用可离子化质子或三氮烯作为芳香卤化物的掩蔽基团的策略。还讨论了前向合成过程，这些过程突出了可以应用于这些卤化底物以生成复杂的π-共轭分子的拓展化学。所提供的实例特定于该小组实验室的工作，但卤化程序足够通用，适用于许多其他共轭框架的应用。