3-bromo-2-methyl-5-(3-cyanophenyl)thiophene | 943920-90-9

• 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-2-methyl-5-(3-cyanophenyl)thiophene
• 英文别名: 3-(4-Bromo-5-methylthiophen-2-yl)benzonitrile；3-(4-bromo-5-methylthiophen-2-yl)benzonitrile
• CAS: 943920-90-9
• 化学式: C₁₂H₈BrNS
• 分子量: 278.172
• InChiKey: PXICQCXXQMLIKY-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-methyl-5-(3-cyanophenyl)thiophene 、 (2-methyl-1-naphthyl)perfluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以43%的产率得到1-(2-methyl-1-naphthyl)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Photochromic diarylethenes with a naphthalene moiety: synthesis, photochromism, and substitution effects

  摘要：

  Five unsymmetrical diarylethenes with a naphthalene moiety were synthesized, and the structures of four diarylethenes were determined by single crystal X-ray diffraction analysis. The naphthalene was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. Their properties, such as photochromism, thermal stability, fatigue resistance, and fluorescence, were investigated systematically. All five diarylethenes, which are thermally stable, exhibit favorable photochromism, and function as notable fluorescence switches in both solution and solid media. The electron-donating substituents effectively suppressed the cycloreversion quantum yield, whereas the electron-withdrawing substituents evidently enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. The results indicated that the naphthalene moiety and the substituent effects played an important role during the process of photoisomerization reaction for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.080
• 作为产物：
  描述：

  间溴苯甲腈 、 4-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以59%的产率得到3-bromo-2-methyl-5-(3-cyanophenyl)thiophene
  参考文献：
  名称：

  The photochromism of unsymmetrical diarylethene isomers with an electron-withdrawing cyano substituent

  摘要：

  Three unsymmetrical isomeric diarylethenes bearing an electron-withdrawing cyano group were synthesized and their structures determined using single-crystal X-ray diffraction analysis. Each of the compounds displayed excellent photochromism in solution, in PMMA film, as well as in the crystalline phase. The isomeric compounds also functioned as a fluorescence switch in PMMA films. The cyclization quantum yield and the absorption maxima of both the ring-opened and ring-closed isomers increased in the order: ortlio- < meta- < para-substitution of the cyano group. Compared with the unsubstituted parent compound, the cycloreversion quantum yield decreased whereas the molar absorption coefficient of the ring-opened and the ring-closed isomers increased significantly when the cyano group was attached at any of the three positions on the terminal benzene ring. Cyclic voltammetry studies indicated that the position of cyano substitution had a marked effect on the electrochemical behaviours of these isomeric diarylethenes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.01.015

文献信息

• The effect of the cyano group position upon unsymmetrical isomeric diarylethenes bearing a pyrrole unit
  作者：Gang Liu、Shouzhi Pu、Xiaomei Wang、Weijun Liu、Congbin Fan

  DOI：10.1016/j.dyepig.2010.12.007

  日期：2011.8

  Four photochromic diarylethenes bearing a pyrrole moiety were synthesized, and the structures of two of the new isomeric compounds were determined by single-crystal X-ray diffraction analysis. Each of the diarylethene derivatives exhibited good photochromism both in solution and in poly(methyl methacrylate) films, which their photoconversion ratios from open-ring to closed-ring isomers were larger

  合成了四个带有吡咯部分的光致变色二蒽，并通过单晶X射线衍射分析确定了两种新的异构化合物的结构。每种二芳基乙烯衍生物在溶液和聚甲基丙烯酸甲酯薄膜中均表现出良好的光致变色性，在光固定态下，它们在己烷中从开环异构体到闭环异构体的光转化率大于89％。它们在己烷和聚甲基丙烯酸甲酯薄膜中也起有效的荧光光电开关的作用。当氰基连接在末端苯环的三个位置中的任何一个位置上时，最大吸收，环化/环还原量子产率和荧光量子产率增加，而摩尔吸收系数和发射峰显着降低。循环伏安图表明氰基的引入降低了开环异构体的带隙而增加了闭环异构体的带隙。氰基及其取代位置可有效地调节这些二芳基乙烯衍生物的光学和电化学行为。
• The photochromism of unsymmetrical diarylethene isomers with an electron-withdrawing cyano substituent
  作者：Shouzhi Pu、Weijun Liu、Gang Liu

  DOI：10.1016/j.dyepig.2010.01.015

  日期：2010.9

  Three unsymmetrical isomeric diarylethenes bearing an electron-withdrawing cyano group were synthesized and their structures determined using single-crystal X-ray diffraction analysis. Each of the compounds displayed excellent photochromism in solution, in PMMA film, as well as in the crystalline phase. The isomeric compounds also functioned as a fluorescence switch in PMMA films. The cyclization quantum yield and the absorption maxima of both the ring-opened and ring-closed isomers increased in the order: ortlio- < meta- < para-substitution of the cyano group. Compared with the unsubstituted parent compound, the cycloreversion quantum yield decreased whereas the molar absorption coefficient of the ring-opened and the ring-closed isomers increased significantly when the cyano group was attached at any of the three positions on the terminal benzene ring. Cyclic voltammetry studies indicated that the position of cyano substitution had a marked effect on the electrochemical behaviours of these isomeric diarylethenes. (C) 2010 Elsevier Ltd. All rights reserved.
• Photochromic diarylethenes with a naphthalene moiety: synthesis, photochromism, and substitution effects
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.tet.2013.04.080

  日期：2013.7

  Five unsymmetrical diarylethenes with a naphthalene moiety were synthesized, and the structures of four diarylethenes were determined by single crystal X-ray diffraction analysis. The naphthalene was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. Their properties, such as photochromism, thermal stability, fatigue resistance, and fluorescence, were investigated systematically. All five diarylethenes, which are thermally stable, exhibit favorable photochromism, and function as notable fluorescence switches in both solution and solid media. The electron-donating substituents effectively suppressed the cycloreversion quantum yield, whereas the electron-withdrawing substituents evidently enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. The results indicated that the naphthalene moiety and the substituent effects played an important role during the process of photoisomerization reaction for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.