3-bromo-4-methyl-2,5-bis(trimethylsilylethynyl)thiophene | 868389-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromo-4-methyl-2,5-bis(trimethylsilylethynyl)thiophene
• CAS: 868389-60-0
• 化学式: C₁₅H₂₁BrSSi₂
• 分子量: 369.473
• InChiKey: QLWDNTNXCJKHMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methyl-2,5-bis(trimethylsilylethynyl)thiophene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 sodium periodate 、 copper(l) iodide 、 正丁基锂 、 air 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 1-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(5-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)thienylethynyl)-3-thienyl]hexafluorocyclopentene
  参考文献：
  名称：

  New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group

  摘要：

  Photoswitching of the intramolecular magnetic interaction was demonstrated using diarylethenes with 2,5-bis(arylethynyl)-4-methyi-3-thienyl side group. Two nitroxide radicals were placed at each end of the 2,5-bis(arylethynyl)-4-methyl-3-thienyI group. Three kinds of aryl groups, 2,5-thienylene, p-phenylene, and m-phenylene groups, were used in the arylethynyl moiety. The diarylethene photoswitching units have an extended pi-conjugated chain on one side of the diarylethene. The photochromic reactivity was dependent on the arylethynyl group. Diarylethenes with m-phenylene group showed an efficient photochromic reactivity. Along with the photochromic reaction the diarylethenes showed photoswitching of an ESR spectrum originating from the change in the magnetic interaction between two unpaired electrons. The open-ring isomer showed stronger exchange interaction than the photogenerated closed-ring isomer. The magnetic interaction between two radicals via the pi-conjugated chain was altered by photocyclization due to the change of the hybrid orbital at the 2-position of the thiophene ring from sp(2) to sp(3).

  DOI：

  10.1021/ja053200p
• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 高碘酸 、 二异丙胺 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 3-bromo-4-methyl-2,5-bis(trimethylsilylethynyl)thiophene
  参考文献：
  名称：

  Synthesis of New Photochromic Diarylethenes Having 2,5-Bis(trimethylsilylethynyl)-3-Thienyl Unit

  摘要：

  New diarylethenes having a trimethylsilylethynyl substituent at the 2,5-position of the thiophene ring were synthesized. Diarylethene moiety are located in the middle of the pi-conjugated chain. These molecules underwent a photochromic reaction in solution. This molecule can be used as a switching unit in the it-conjugated polymer or oligomer.

  DOI：

  10.1080/15421400590946190

文献信息

• Synthesis, characterization, and properties of some bisacetylide and binuclear acetylide gold(I) compounds based on the photochromic dithienylethene unit
  作者：Yan Lin、Chuanyin Jiang、Fang Hu、Jun Yin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1016/j.dyepig.2013.08.013

  日期：2013.12

  l]hexafluorocyclopentene together with three dinuclear acetylide gold(I) complexes LAu-CC-dithienylethene-CC-AuL in which L = PPh3 or PCy3, containing the photochromic dithienylethene unit. The photophysical properties of these new complexes are compared and contrasted with those of some previously reported dithienylethene complexes. It has been revealed that these compounds with dithienyletehene units

  我们报告了两个新的双乙炔化合物，1,2-双（2-乙炔基-5-甲基-3-噻吩基）全氟环戊烯和1- [2-甲基-5-苯基-3-噻吩基] -2-的合成与表征[4-甲基-2,5-双（乙炔基）-3-噻吩基]六氟环戊烯与三个双核乙炔金（I）配合物LAu-C C-二噻吩基乙烯-CC-AuL，其中L = PPh3或PCy3，包含光致变色二噻吩基乙烯单元。将这些新配合物的光物理性质与某些先前报道的二噻吩基乙烯配合物的光物理性质进行了比较和对比。已经发现这些具有二噻吩并丁烯单元的化合物显示出光致变色行为，但是它们的吸收光谱，环化/环还原量子产率，光致变色过程的效率以及在光固定态下从开环到闭环异构体的转化都是一样的。高度依赖于双炔基部分的取代位以及是否存在双炔金属化。还发现光致变色过程通过用紫外线和可见光交替照射而显示出完全可逆性。