1,2-bis{2-n-propyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopent-1-ene | 944243-54-3

• 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: 1,2-bis{2-n-propyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopent-1-ene
• 英文别名: 1,2-bis{2-n-propyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopentene；2-[4-[2-[5-(1,3-Dioxolan-2-yl)-2-propylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-propylthiophen-2-yl]-1,3-dioxolane；2-[4-[2-[5-(1,3-dioxolan-2-yl)-2-propylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-propylthiophen-2-yl]-1,3-dioxolane
• CAS: 944243-54-3
• 化学式: C₂₅H₂₆F₆O₄S₂
• 分子量: 568.601
• InChiKey: BESPEYVWXPBSDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis{2-n-propyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopent-1-ene 在 吡啶 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以83%的产率得到1,2-bis(2-n-propyl-5-formyl-3-thienyl)perfluorocyclopent-1-ene
  参考文献：
  名称：

  Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives

  摘要：

  Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl) perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.049
• 作为产物：
  描述：

  5-丙基-噻吩-2-甲醛 在 正丁基锂 、 溴 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 27.67h， 生成 1,2-bis{2-n-propyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopent-1-ene
  参考文献：
  名称：

  Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives

  摘要：

  Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl) perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.049

文献信息

• Substituent effects on the properties of photochromic diarylethenes
  作者：Shouzhi Pu、Chunhong Zheng、Zhanggao Le、Gang Liu、Congbin Fan

  DOI：10.1016/j.tet.2008.01.025

  日期：2008.3

  Photochromic symmetrical diarylethenes 1o–5o bearing different electron-donating or electron-withdrawing substitutents have been synthesized, and the structures of 1o, 2o, 4o, and 5o were determined by single-crystal X-ray diffraction analysis. Substitutent effects on their optoelectronic properties, including photochromism, fluorescence, and electrochemical properties were investigated in detail.

  已经合成了带有不同给电子或吸电子取代基的光致变色对称二芳基蒽1o - 5o，并通过单晶X射线衍射分析确定了1o，2o，4o和5o的结构。详细研究了取代基对其光电性能的影响，包括光致变色，荧光和电化学性能。吸电子取代基可使二芳烃的吸收最大值显着移至更长的波长并增加其环化量子产率，而摩尔吸收系数随电子给体能力的增加而增加。双芳烃1，2，和4在溶液中和在单结晶相表现出良好的光致变色; 然而，双芳烃5在结晶相中没有显示出光致变色，因为活性碳之间的距离变得大于4.2。二芳基乙烯1 - 3在用UV和可见光，并在光稳态其荧光转换交替照射表现出良好的荧光开关均大于80％于己烷中。此外，循环伏安法测试表明，不同的供电子和吸电子取代基对这些二芳烃的电化学行为有显着影响。