3-bromo-2-ethyl-5-(1,3-dioxolane)thiophene | 872716-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-bromo-2-ethyl-5-(1,3-dioxolane)thiophene
• 英文别名: 2-(4-bromo-5-ethylthiophen-2-yl)-1,3-dioxolane
• CAS: 872716-06-8
• 化学式: C₉H₁₁BrO₂S
• 分子量: 263.155
• InChiKey: UOSVZQVIMSRXKF-UHFFFAOYSA-N

物化性质

• 沸点：
  314.0±42.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-bromo-2-ethyl-5-(1,3-dioxolane)thiophene 、 1-(2-ethyl-1-benzothiophen-3-yl)heptafluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 以43.5%的产率得到1-(2-ethyl-3-benzothienyl)-2-{2-ethyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopentene
  参考文献：
  名称：

  具有苯并噻吩和正烷基噻吩单元的二芳基乙烯衍生物的合成和光电性能

  摘要：

  摘要 合成了六种新的同时具有苯并噻吩和正烷基噻吩单元的不对称二芳基乙烯。二芳基乙烯2a-6a的结构由单晶X射线衍射分析确定。结果表明，烷基链长对这些二芳基乙烯的光电性能有显着影响，包括光致变色、抗疲劳、荧光和电化学性能。长烷基链可以增加环化/环回复量子产率，但会降低二芳基乙烯 1 – 6 的吸收最大值。长烷基链还可以导致闭环异构体 1b-6b 在溶液和 PMMA 膜中的吸收最大值发生显着的红移。所有这些二芳基乙烯衍生物在己烷中都显示出良好的荧光转换（猝灭至约 10%）。随着烷基链长度变长，二芳基乙烯1-6的发射强度和荧光量子产率逐渐降低。此外，循环伏安测试表明，烷基链长对这些二芳基乙烯的电化学行为有显着影响。

  DOI：

  10.1016/j.molstruc.2008.08.023
• 作为产物：
  描述：

  5-乙基-2-噻吩甲醛 在 溴 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 3-bromo-2-ethyl-5-(1,3-dioxolane)thiophene
  参考文献：
  名称：

  1,2-Bis[5-(1,3-dioxolan-2-yl)-2-ethyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, a photochromic dithienylethene

  摘要：

  The title compound, C23H22F6O4S2, a photochromic dithienylethene, is a promising material for optical storage and other optoelectrical devices. The molecule adopts a photoactive antiparallel conformation in the crystalline state. The distance between the two reactive C atoms which are involved in potential ring closure is 3.829 (4) angstrom. The dihedral angles between the central cyclopentene ring and the adjacent thiophene rings are 55.38 (7) and 54.81 (9)degrees. The colourless crystals turn magenta when exposed to UV radiation and the process is reversible.

  DOI：

  10.1107/s0108270105025758

文献信息

• Synthesis, crystal structure and characterization of photochromic 1,2-bis{2-ethyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopentene
  作者：Shouzhi Pu、Tianshe Yang、Ruji Wang、Fushi Zhang、Jingkun Xu

  DOI：10.1016/j.saa.2006.03.014

  日期：2007.2

  A novel photochromic diarylethene, 1,2-bis2-ethyl-5-[2-(1,3-dioxolane)1-3-thienyllperfluorocyclopentene (BEDTP), was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. Its photochromic and fluorescent properties were also investigated. The results showed that this compound exhibited reversible photochromism, changing from colorless to magenta after irradiation with UV light both in solution and in the crystalline phase. In hexane solution, the open-ring isomer of BEDTP exhibited relatively strong fluorescence at 400 nm when excited at 282 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 254 nm light and its closed-ring isomer showed almost no fluorescence. (c) 2006 Elsevier B.V. All rights reserved.