3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine | 634591-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
• 英文别名: 3,3-bis[octadecyloxymethyl]-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
• CAS: 634591-77-8
• 化学式: C₄₅H₈₄O₄S
• 分子量: 721.226
• InChiKey: IQQGNWOEOGDGAR-UHFFFAOYSA-N

物化性质

• 沸点：
  717.8±40.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.06
• 重原子数：
  50.0
• 可旋转键数：
  38.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以90%的产率得到6,8-dibromo-3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
  参考文献：
  名称：

  Spray Coatable Electrochromic Dioxythiophene Polymers with High Coloration Efficiencies

  摘要：

  Four new disubstituted propylenedioxythiophene polymers have been synthesized by Grignard metathesis on the 1-5 g scale. All polymers were found to be soluble in chloroform, methylene chloride, toluene, and tetrahydrofuran and were fully structurally characterized having GPC determined number-average molecular weights ranging from 33000 to 47000 g mol(-1). Dilute polymer solutions in toluene exhibited strong red fluorescence with moderate quantum efficiencies from 0.38 to 0.50. Homogeneous thin films were formed by electropolymerization and spray casting polymer solutions onto ITO coated glass slides at thicknesses of ca. 150 nm. The films were electroactive, switching from a dark blue-purple to a transmissive sky blue upon p-doping, often with subsecond switching times, and high electrochromic contrast luminance changes (% DeltaY) of 40-70%. These studies revealed that the branched derivatives, [poly(3,3-bis(2-ethylhexyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4] dioxepine)] and [poly(6,8-dibromo-3,3-bis(2-ethylhexyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4]dioxepine)], gave an electrochemical response and associated color change over a much smaller voltage range in comparison to the linear chain substituted derivatives, [poly(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine)] and [poly(3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4]dioxepine)]. Composite coloration efficiency values were found up to 1365 cm(2)/C; this was considerably larger than values obtained from previously studied alkylenedioxythiophene based polymers (similar to375 cm(2)/C).

  DOI：

  10.1021/ma049222y
• 作为产物：
  描述：

  3,4-二甲氧基噻吩 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
  参考文献：
  名称：

  Spray Coatable Electrochromic Dioxythiophene Polymers with High Coloration Efficiencies

  摘要：

  Four new disubstituted propylenedioxythiophene polymers have been synthesized by Grignard metathesis on the 1-5 g scale. All polymers were found to be soluble in chloroform, methylene chloride, toluene, and tetrahydrofuran and were fully structurally characterized having GPC determined number-average molecular weights ranging from 33000 to 47000 g mol(-1). Dilute polymer solutions in toluene exhibited strong red fluorescence with moderate quantum efficiencies from 0.38 to 0.50. Homogeneous thin films were formed by electropolymerization and spray casting polymer solutions onto ITO coated glass slides at thicknesses of ca. 150 nm. The films were electroactive, switching from a dark blue-purple to a transmissive sky blue upon p-doping, often with subsecond switching times, and high electrochromic contrast luminance changes (% DeltaY) of 40-70%. These studies revealed that the branched derivatives, [poly(3,3-bis(2-ethylhexyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4] dioxepine)] and [poly(6,8-dibromo-3,3-bis(2-ethylhexyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4]dioxepine)], gave an electrochemical response and associated color change over a much smaller voltage range in comparison to the linear chain substituted derivatives, [poly(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine)] and [poly(3,3-bis(octadecyloxymethyl)-3,4-dihydro-2H-thieno[3,4-b] [1,4]dioxepine)]. Composite coloration efficiency values were found up to 1365 cm(2)/C; this was considerably larger than values obtained from previously studied alkylenedioxythiophene based polymers (similar to375 cm(2)/C).

  DOI：

  10.1021/ma049222y

文献信息

• Chain-Growth Polymerization of 2-Chlorothiophenes Promoted by Lewis Acids
  作者：Baltasar Bonillo、Timothy M. Swager

  DOI：10.1021/ja308498h

  日期：2012.11.21

  Lewis acids promote the polymerization of several 2-chloroalkylenedioxythiophenes, providing high-molecular-weight conjugated polymers. The proposed mechanism is a cationic chain-growth polymerization, as confirmed by end-capping reactions and a linear correlation of molecular weight with percent conversion. The "living" character of this process was used to prepare new block copolymers.