4,4′-dibromo-2,2′-bis(1,3-dioxolan-2-yl)-3,3′-bithienyl | 53938-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,4′-dibromo-2,2′-bis(1,3-dioxolan-2-yl)-3,3′-bithienyl
• 英文别名: 4,4'-Dibrom-3,3'-bithienyl-2,2'-dialdehyd diethylenacetal；2,2'-(4,4'-dibromo-[3,3']bithiophenyl-2,2'-diyl)-bis-[1,3]dioxolane；2-[4-Bromo-3-[4-bromo-2-(1,3-dioxolan-2-yl)thiophen-3-yl]thiophen-2-yl]-1,3-dioxolane
• CAS: 53938-82-2
• 化学式: C₁₄H₁₂Br₂O₄S₂
• 分子量: 468.187
• InChiKey: PLCYPKXKOVYAAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4′-dibromo-2,2′-bis(1,3-dioxolan-2-yl)-3,3′-bithienyl 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 4.5h， 生成 2,2′-bis(1,3-dioxolan-2-yl)-4,4′-bishydroxymethyl-3,3′-bithienyl
  参考文献：
  名称：

  Redox-Driven Molecular Switches Consisting of Bis(benzodithiolyl)bithienyl Scaffold and Mesogenic Moieties: Synthesis and Complexes with Liquid Crystalline Polymer

  摘要：

  Molecular switches composed of a benzodithiolylbithienyl scaffold and biphenyl or terphenyl mesogenic substituents were designed and synthesized. The molecular switches could undergo redox-triggered interconversion between the cationic form and cyclized neutral form, and this was confirmed using cyclic voltammnetry and UV-vis spectroscopy. Binary complexes consisting of the molecular switches and a liquid crystalline polymer (LCP) were prepared to investigate the function of these redox-active molecular switches as actuating dopants. X-ray diffraction measurements were performed to determine the differences between the layer spacings of the complexes in the liquid crystalline phase with the oxidized and reduced states of the molecular switches. The LCP that was doped with the oxidized cationic form of the molecular switch had layer spacings that were up to 4% larger than the layer spacings in the polymer that was doped with the reduced cyclized molecular switch. Our approach will allow stimulus-responsive deformable materials to be constructed and give an impetus for fabricating redox-driven soft actuators.

  DOI：

  10.1021/jo501072u
• 作为产物：
  描述：

  4,4'-dibromo-2,2'-diformyl-3,3'-bithienyl 、 乙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以95%的产率得到4,4′-dibromo-2,2′-bis(1,3-dioxolan-2-yl)-3,3′-bithienyl
  参考文献：
  名称：

  Redox-Driven Molecular Switches Consisting of Bis(benzodithiolyl)bithienyl Scaffold and Mesogenic Moieties: Synthesis and Complexes with Liquid Crystalline Polymer

  摘要：

  Molecular switches composed of a benzodithiolylbithienyl scaffold and biphenyl or terphenyl mesogenic substituents were designed and synthesized. The molecular switches could undergo redox-triggered interconversion between the cationic form and cyclized neutral form, and this was confirmed using cyclic voltammnetry and UV-vis spectroscopy. Binary complexes consisting of the molecular switches and a liquid crystalline polymer (LCP) were prepared to investigate the function of these redox-active molecular switches as actuating dopants. X-ray diffraction measurements were performed to determine the differences between the layer spacings of the complexes in the liquid crystalline phase with the oxidized and reduced states of the molecular switches. The LCP that was doped with the oxidized cationic form of the molecular switch had layer spacings that were up to 4% larger than the layer spacings in the polymer that was doped with the reduced cyclized molecular switch. Our approach will allow stimulus-responsive deformable materials to be constructed and give an impetus for fabricating redox-driven soft actuators.

  DOI：

  10.1021/jo501072u

文献信息

• Redox-Driven Molecular Switches Consisting of Bis(benzodithiolyl)bithienyl Scaffold and Mesogenic Moieties: Synthesis and Complexes with Liquid Crystalline Polymer
  作者：Toshihiro Ohtake、Hideki Tanaka、Tetsuro Matsumoto、Mutsumi Kimura、Akira Ohta

  DOI：10.1021/jo501072u

  日期：2014.7.18

  Molecular switches composed of a benzodithiolylbithienyl scaffold and biphenyl or terphenyl mesogenic substituents were designed and synthesized. The molecular switches could undergo redox-triggered interconversion between the cationic form and cyclized neutral form, and this was confirmed using cyclic voltammnetry and UV-vis spectroscopy. Binary complexes consisting of the molecular switches and a liquid crystalline polymer (LCP) were prepared to investigate the function of these redox-active molecular switches as actuating dopants. X-ray diffraction measurements were performed to determine the differences between the layer spacings of the complexes in the liquid crystalline phase with the oxidized and reduced states of the molecular switches. The LCP that was doped with the oxidized cationic form of the molecular switch had layer spacings that were up to 4% larger than the layer spacings in the polymer that was doped with the reduced cyclized molecular switch. Our approach will allow stimulus-responsive deformable materials to be constructed and give an impetus for fabricating redox-driven soft actuators.