4,10-bis(5-octyl-2-thienyl)-6,12-bis((triisopropylsilyl)-ethynyl)anthanthrene | 1574519-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4,10-bis(5-octyl-2-thienyl)-6,12-bis((triisopropylsilyl)-ethynyl)anthanthrene
• CAS: 1574519-14-4
• 化学式: C₆₈H₈₈S₂Si₂
• 分子量: 1025.75
• InChiKey: ATLNKBWFZLMDGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.73
• 重原子数：
  72.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,10-bis(5-octyl-2-thienyl)-6,12-bis((triisopropylsilyl)-ethynyl)anthanthrene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 tBu₃PHBF₄ 、 三异丙基硅基乙炔 、 四丁基氟化铵 、 二异丙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 4,10-bis(5-octyl-2-thienyl)-6,12-bis((5-octyl-2-thienyl)-ethynyl)anthanthrene
  参考文献：
  名称：

  Cruciform Alkynylated Anthanthrene Derivatives: A Structure–Properties Relationship Case Study

  摘要：

  An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds using Sonogashira couplings steps was developed. Acetylenic linkers were used to effectively extend the π-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their optoelectronic properties. Structure-property relationships supported by DFT calculations indicated more effective π-conjugation along the 6,12 axis than along the 4,10 axis. These molecules displayed strong J-aggregation both in solution and in the solid state and proved to be highly photostable with reversible redox processes, which are properties of interest in materials sciences.

  DOI：

  10.1021/jo402674m
• 作为产物：
  描述：

  4,10-dibromo-6,12-bis((triisopropylsilyl)ethynyl)anthanthrene 、 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 以75%的产率得到4,10-bis(5-octyl-2-thienyl)-6,12-bis((triisopropylsilyl)-ethynyl)anthanthrene
  参考文献：
  名称：

  Cruciform Alkynylated Anthanthrene Derivatives: A Structure–Properties Relationship Case Study

  摘要：

  An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds using Sonogashira couplings steps was developed. Acetylenic linkers were used to effectively extend the π-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their optoelectronic properties. Structure-property relationships supported by DFT calculations indicated more effective π-conjugation along the 6,12 axis than along the 4,10 axis. These molecules displayed strong J-aggregation both in solution and in the solid state and proved to be highly photostable with reversible redox processes, which are properties of interest in materials sciences.

  DOI：

  10.1021/jo402674m