(E,E,E)-1,3,5-tris[4-(tert-butylthio)styryl]benzene | 500530-88-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E,E,E)-1,3,5-tris[4-(tert-butylthio)styryl]benzene
• 英文别名: 1,3,5-tris[(E)-2-(4-tert-butylsulfanylphenyl)ethenyl]benzene
• CAS: 500530-88-1
• 化学式: C₄₂H₄₈S₃
• 分子量: 649.041
• InChiKey: WZQCUYPBYOFCBB-DZURWXOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (E,E,E)-1,3,5-tris[4-(tert-butylthio)styryl]benzene 在 三溴化硼 、 碘 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 以76%的产率得到(E,E,E)-1,3,5-tris[4-(acetylthio)styryl]benzene
  参考文献：
  名称：

  Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

  摘要：

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

  DOI：

  10.1021/jo0263770
• 作为产物：
  描述：

  1-溴-4-(叔丁基磺酰基)苯 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (E,E,E)-1,3,5-tris[4-(tert-butylthio)styryl]benzene
  参考文献：
  名称：

  Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

  摘要：

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

  DOI：

  10.1021/jo0263770

文献信息

• Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)
  作者：Nicolai Stuhr-Hansen、Jørn B. Christensen、Niels Harrit、Thomas Bjørnholm

  DOI：10.1021/jo0263770

  日期：2003.2.1

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.