(E,E)-1,4-bis[4-{(E)-4-(tert-butylthio)styryl}styryl]-2,5-didodecylbenzene | 500530-86-9

• 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: (E,E)-1,4-bis[4-{(E)-4-(tert-butylthio)styryl}styryl]-2,5-didodecylbenzene
• 英文别名: 1,4-bis[(E)-2-[4-[(E)-2-(4-tert-butylsulfanylphenyl)ethenyl]phenyl]ethenyl]-2,5-didodecylbenzene
• CAS: 500530-86-9
• 化学式: C₇₀H₉₄S₂
• 分子量: 999.648
• InChiKey: KDKMLJUCPJYMBT-IDEBLROHSA-N

物化性质

• 沸点：
  971.2±65.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  26.4
• 重原子数：
  72
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (E,E)-1,4-bis[4-{(E)-4-(tert-butylthio)styryl}styryl]-2,5-didodecylbenzene 在 三溴化硼 、 碘 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 以46%的产率得到(E,E)-1,4-bis[4-{(E)-4-(acetylthio)styryl}styryl]-2,5-didodecylbenzene
  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：

  4-(叔丁基磺酰基)苯甲醛 在 potassium tert-butylate 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 28.0h， 生成 (E,E)-1,4-bis[4-{(E)-4-(tert-butylthio)styryl}styryl]-2,5-didodecylbenzene
  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.