5,8-bis(5-bromo-3-n-octylthien-2-yl)-2,11-dithia[3.3]paracyclophane | 704886-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5,8-bis(5-bromo-3-n-octylthien-2-yl)-2,11-dithia[3.3]paracyclophane
• 英文别名: 6,17-Bis(5-bromo-3-octylthiophen-2-yl)-3,10-dithiatricyclo[10.2.2.25,8]octadeca-1(15),5(18),6,8(17),12(16),13-hexaene；6,17-bis(5-bromo-3-octylthiophen-2-yl)-3,10-dithiatricyclo[10.2.2.25,8]octadeca-1(15),5(18),6,8(17),12(16),13-hexaene
• CAS: 704886-30-6
• 化学式: C₄₀H₅₀Br₂S₄
• 分子量: 818.909
• InChiKey: HITNAUAJRDTELF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-dibromo-2,5-bis(methoxymethyl)benzene 在 氢氧化钾 、 四(三苯基膦)钯 、 氢溴酸 、 溴 、 溶剂黄146 、 硫脲 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 74.0h， 生成 5,8-bis(5-bromo-3-n-octylthien-2-yl)-2,11-dithia[3.3]paracyclophane
  参考文献：
  名称：

  Alternating Aromatic and Transannular Chromophores with and without Linker:  Effect of Transannular π−π Interaction on the Optical Property of Dithiaparacyclophane-based Copolymers

  摘要：

  A series of bithiophene-cyclophane (PPP-type), acetylene-fluorene-acetylene-cyclophane (PPE-type), and ethylene-fluorene-ethylene-cyclophane (PPV-type) copolymers, namely, 4-6, was synthesized via a nickel-catalyzed reaction, a palladium-catalyzed Sonagashira reaction, and a Heck coupling, respectively. Unlike in the fluorene-cyclophane copolymer 3, the transannular pi-pi interaction of the cylophane unit in copolymer 4 resulted in a significant blue shift in its emission spectrum compared to a reference polymer, giving it an essentially blue emitting light. By introducing an acetylene or ethylene linker in going from 3 to 5 or 6, the effective conjugation in the polymer backbone due to higher rigidity in coplanarity decreased the effect of the transannular pi-pi interaction. While the PPV-type copolymer 6 still exhibited an appreciable red shift in both absorption and emission with respect to a reference polymer, negligible shifts were observed for copolymer 5.

  DOI：

  10.1021/ma035902+

文献信息

• Alternating Aromatic and Transannular Chromophores with and without Linker:  Effect of Transannular π−π Interaction on the Optical Property of Dithiaparacyclophane-based Copolymers
  作者：Weiling Wang、Jianwei Xu、Yee-Hing Lai、Fuke Wang

  DOI：10.1021/ma035902+

  日期：2004.5.1

  A series of bithiophene-cyclophane (PPP-type), acetylene-fluorene-acetylene-cyclophane (PPE-type), and ethylene-fluorene-ethylene-cyclophane (PPV-type) copolymers, namely, 4-6, was synthesized via a nickel-catalyzed reaction, a palladium-catalyzed Sonagashira reaction, and a Heck coupling, respectively. Unlike in the fluorene-cyclophane copolymer 3, the transannular pi-pi interaction of the cylophane unit in copolymer 4 resulted in a significant blue shift in its emission spectrum compared to a reference polymer, giving it an essentially blue emitting light. By introducing an acetylene or ethylene linker in going from 3 to 5 or 6, the effective conjugation in the polymer backbone due to higher rigidity in coplanarity decreased the effect of the transannular pi-pi interaction. While the PPV-type copolymer 6 still exhibited an appreciable red shift in both absorption and emission with respect to a reference polymer, negligible shifts were observed for copolymer 5.