3-bromo-2-methyl-5-(3-chlorophenyl)thiophene | 1132816-35-3

• 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: 3-bromo-2-methyl-5-(3-chlorophenyl)thiophene
• 英文别名: 3-Bromo-5-(3-chlorophenyl)-2-methylthiophene；3-bromo-5-(3-chlorophenyl)-2-methylthiophene
• CAS: 1132816-35-3
• 化学式: C₁₁H₈BrClS
• 分子量: 287.608
• InChiKey: FMGBTSOHLQUERG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-methyl-1-naphthyl)perfluorocyclopentene 、 3-bromo-2-methyl-5-(3-chlorophenyl)thiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以38%的产率得到1-(2-methyl-1-naphthyl)-2-[2-methyl-5-(3-chlorophenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Synthesis and photochromism of isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties

  摘要：

  Three new isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties were synthesized. Their photochromism, fluorescence and electrochemistry properties were investigated in detail. Each of the diarylethene derivatives showed notable photochromism and functioned as an effective fluorescent switch both in solution and in PMMA films. The cyclization quantum yield and the molar absorption coefficients of both the open- and closed-ring isomers were found to decrease based on the position of the chloro substituent attached to the terminal benzene ring as follows: para- > meta- > the ortho-position. Consequently, the cycloreversion quantum yield would increase para- to meta- to ortho-chloro substitution. When compared with the unsubstituted parent compound, the presence of the chloro substituent on the terminal benzene ring of these diarylethenes, regardless of the substitution position, would considerably lower the band gaps of the open- and closed-ring isomers. Our results indicated that the chlorine atom and its substitution position have significant influence on the optical and electrochemical properties of the diarylethenes bearing a naphthalene moiety. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.06.003
• 作为产物：
  描述：

  间氯溴苯 、 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， 反应 16.0h， 以66%的产率得到3-bromo-2-methyl-5-(3-chlorophenyl)thiophene
  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

文献信息

• Synthesis and photochromism of isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Shiqiang Cui、Weijun Liu

  DOI：10.1016/j.jphotochem.2012.06.003

  日期：2012.9

  Three new isomeric unsymmetrical diarylethenes bearing both naphthalene and thiophene moieties were synthesized. Their photochromism, fluorescence and electrochemistry properties were investigated in detail. Each of the diarylethene derivatives showed notable photochromism and functioned as an effective fluorescent switch both in solution and in PMMA films. The cyclization quantum yield and the molar absorption coefficients of both the open- and closed-ring isomers were found to decrease based on the position of the chloro substituent attached to the terminal benzene ring as follows: para- > meta- > the ortho-position. Consequently, the cycloreversion quantum yield would increase para- to meta- to ortho-chloro substitution. When compared with the unsubstituted parent compound, the presence of the chloro substituent on the terminal benzene ring of these diarylethenes, regardless of the substitution position, would considerably lower the band gaps of the open- and closed-ring isomers. Our results indicated that the chlorine atom and its substitution position have significant influence on the optical and electrochemical properties of the diarylethenes bearing a naphthalene moiety. (C) 2012 Elsevier B.V. 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.