3,4-bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene | 888743-90-6

• 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: 3,4-bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene
• 英文别名: 5-Iodo-3-[4-(5-iodo-2-methylthiophen-3-yl)-2,5-dihydrothiophen-3-yl]-2-methylthiophene；5-iodo-3-[4-(5-iodo-2-methylthiophen-3-yl)-2,5-dihydrothiophen-3-yl]-2-methylthiophene
• CAS: 888743-90-6
• 化学式: C₁₄H₁₂I₂S₃
• 分子量: 530.256
• InChiKey: FPGUGJMLILMZMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.34h， 生成
  参考文献：
  名称：

  Photoconversion of a Protonated Diarylethene Derivative

  摘要：

  A photochromic diarylethene with N,N-dimethyl substituted group 1a was prepared. 1a showed ring-opening and ring-closing photoisomerization with UV/vis light irradiation. Treatment of 1a with CF3COOH produced a protonated diarylethene 1aH. With UV light irradiation, 1aH photoconverted to protonated ring-closed isomer 1c, which is photoinactive. It is found that 1c is hydrophilic and 1aH is hydrophobic.

  DOI：

  10.1021/jp3070163
• 作为产物：
  描述：

  5,5''-二氯-2',5'-二氢-2,2''-二甲基-3,3':4',3''-三联噻吩 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以63%的产率得到3,4-bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene
  参考文献：
  名称：

  3,4-Bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene: A Powerful Synthon­ for the Preparation of Photochromic Dithienylethene Derivatives

  摘要：

  合成了二噻烯合成子，3,4-双(5-碘-2-甲基噻吩-3-基)-2,5-二氢噻吩，并将其作为起始材料，通过铃木交叉偶联反应制备了几种光致变色二噻烯衍生物。该二噻烯合成子在室温暗处储存时稳定。

  DOI：

  10.1055/s-2006-933108

文献信息

• Combination of fluorescent switch and electrochemical switch based on a photochromic diarylethene
  作者：Nan Xie、Yi Chen

  DOI：10.1039/b609156c

  日期：——

  photochromic diarylethene with oligothiophene side arm substituents has been synthesized. This diarylethene undergoes excellent photoisomerization with UV/Vis light irradiation, and shows fluorescence emission and electrochemical behavior. Both the fluorescence emission and oxidation/reduction potential are reversible based on the ring-opening and ring-closing photoisomerization of diarylethene with UV/Vis

  已经合成了具有低聚噻吩侧臂取代基的新的光致变色二芳基乙烯。该二芳基乙烯在紫外线/可见光照射下会经历出色的光异构化，并显示出荧光发射和电化学行为。荧光发射和氧化/减少基于二芳基乙烯在UV / Vis光照射下的开环和闭环光异构化，其电势是可逆的，可以用作荧光和电化学开关。此外，对二芳基乙烯观察到了光致变色和电致变色的组合：闭环反应可以通过电化学来触发氧化作用 而开环反应必须是光化学驱动的。
• 3,4-Bis(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene: A Powerful Synthon­ for the Preparation of Photochromic Dithienylethene Derivatives
  作者：Yi Chen、Nan Xie、De Xing Zeng

  DOI：10.1055/s-2006-933108

  日期：——

  A dithienylethene synthon, 3,4-bis-(5-iodo-2-methylthien-3-yl)-2,5-dihydrothiophene, was prepared and used as a starting material for the preparation of several photochromic dithien­ylethene derivatives via Suzuki cross-coupling reactions. The dithienylethene synthon was stable once stored in the dark at room temperature.

  合成了二噻烯合成子，3,4-双(5-碘-2-甲基噻吩-3-基)-2,5-二氢噻吩，并将其作为起始材料，通过铃木交叉偶联反应制备了几种光致变色二噻烯衍生物。该二噻烯合成子在室温暗处储存时稳定。
• Photoconversion of a Protonated Diarylethene Derivative
  作者：Huan-huan Liu、Xu Zhang、Zeng Gao、Yi Chen

  DOI：10.1021/jp3070163

  日期：2012.10.11

  A photochromic diarylethene with N,N-dimethyl substituted group 1a was prepared. 1a showed ring-opening and ring-closing photoisomerization with UV/vis light irradiation. Treatment of 1a with CF3COOH produced a protonated diarylethene 1aH. With UV light irradiation, 1aH photoconverted to protonated ring-closed isomer 1c, which is photoinactive. It is found that 1c is hydrophilic and 1aH is hydrophobic.