3-bromo-2-methyl-5-(3-methoxyphenyl)thiophene | 914360-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-2-methyl-5-(3-methoxyphenyl)thiophene
• 英文别名: 3-bromo-5-(3-methoxyphenyl)-2-methylthiophene；3-Bromo-2-methyl-5-(3-methoxylphenyl)thiophene
• CAS: 914360-27-3
• 化学式: C₁₂H₁₁BrOS
• 分子量: 283.189
• InChiKey: SSNFSTFTKZNZMG-UHFFFAOYSA-N

物化性质

• 沸点：
  221 °C
• 密度：
  1.411±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.5
• 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-methoxyphenyl)thiophene 在 正丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 24.0h， 生成 3-(4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(pyridin-4-yl)thiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)phenol
  参考文献：
  名称：

  衍生自 Pyridinium-Phenolates 和 Bis(thienyl)ethane 的可切换 Mesomeric 甜菜碱

  摘要：

  制备了一系列具有中心 BTE 核的吡啶-酚盐型异构可切换内消旋甜菜碱，并研究了它们从交叉共轭体系到共轭、交叉共轭和两性离子闭环形式的光化学转化，包括 NMR 特性、红移位移和灭绝。

  DOI：

  10.1002/ejoc.202100279
• 作为产物：
  描述：

  3,5-二溴-2-甲基噻吩 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 、 水 为溶剂， 反应 30.17h， 生成 3-bromo-2-methyl-5-(3-methoxyphenyl)thiophene
  参考文献：
  名称：

  衍生自 Pyridinium-Phenolates 和 Bis(thienyl)ethane 的可切换 Mesomeric 甜菜碱

  摘要：

  制备了一系列具有中心 BTE 核的吡啶-酚盐型异构可切换内消旋甜菜碱，并研究了它们从交叉共轭体系到共轭、交叉共轭和两性离子闭环形式的光化学转化，包括 NMR 特性、红移位移和灭绝。

  DOI：

  10.1002/ejoc.202100279

文献信息

• Photochromism of new unsymmetrical isomeric diarylethenes bearing a methoxyl group
  作者：Shouzhi Pu、Weijun Liu、Wenjuan Miao

  DOI：10.1002/poc.1545

  日期：2009.10

  substituent position effect of methoxyl group on their properties, including photochromism and fluorescence both in hexane solution and in PMMA film, and their electrochemical properties, were investigated in detail. These diarylethenes showed good photochromism both in solution and in PMMA film. For the same photochromic diarylethene backbone, the electron‐ donating methoxyl substituent can effectively

  在末端苯环的邻位，间位和对位具有甲氧基取代基的三个新的不对称异构二芳烃，即1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5- （2-甲氧基苯基）-3-噻吩基]全氟环戊烯（1o），1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5-（3-甲氧基苯基）-3-噻吩基]全氟环戊烯（2o）和1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5-（4-甲氧基苯基）-3-噻吩基]全氟环戊烯（3o），已经合成。详细研究了甲氧基的取代基位置对其性能的影响，包括在己烷溶液和PMMA膜中的光致变色和荧光以及它们的电化学性能。这些双芳烃在溶液和PMMA膜中均显示出良好的光致变色性。对于相同的光致变色二芳基乙烯主链，与先前报道的带有氯原子的二芳烃相比，给电子的甲氧基取代基可以有效地降低环化量子产率并提高环还原量子产率。二芳烃1o – 3o通过在己烷和PMMA膜中进行光辐照显示出清晰的荧光开关。此外
• Electron-donating methoxyl group position effect on properties of diarylethene derivatives having a pyrazole unit
  作者：Tianshe Yang、Shouzhi Pu、Bing Chen、Jingkun Xu

  DOI：10.1139/v06-182

  日期：2007.1.1

  New types of asymmetrical photochromic diarylethene derivatives having a pyrazole unit, namely 1-[1,3,5-trimethyl-1-pyrazol-4-yl],2-[2-methyl-5-(4-methoxylphenyl)-1-thien-3-yl]perfluorocyclopentene (1a), 1-[1,3,5-trimethylpyrazol-4-yl],2-[2-methyl-5-(3-methoxylphenyl)-1-thien-3-yl] perfluorocyclopentene (2a), 1-[1,3,5-trimethyl-pyrazol-4-yl],2-[2-methyl-5-(2-methoxylphenyl)-1-thien-3-yl]perfluorocyclopentene (3a), and 1-[1,3,5-trimethyl-pyrazol-4-yl],2-[2-methyl-5-phenyl-1-thien-3-yl]perfluorocyclopentene (4a), were synthesized. Their optical and electrochemical properties, such as photochromism, photochromic cyclization–cycloreversion kinetics, and fluorescence and electrochemical properties were investigated in detail. The results show that all of these compounds have good photochromism, high cycloreversion quantum yield, and relatively strong fluorescence. Their cyclization-cycloreversion processes were determined to be zeroth to first order reactions. The oxidations of diarylethenes 1a–4a were initiated at 0.73, 1.11, 0.79, and 1.03 V, respectively. Furthermore, introduction of the electron-donating methoxyl group at different positions of the terminal phenyl ring was found to strongly influence these optical and electrochemical properties.Key words: photochromism, diarylethene, electron-donating group, optical and electrochemical properties.

  2-[2-甲基-5-(3-甲氧基苯基)-1-噻吩-3-基]全氟环戊烯 (2a)、1-[1,3,5-三甲基吡唑-4-基]、2-[2-甲基-5-(2-甲氧基苯基)-1-噻吩-3-基]全氟环戊烯 (3a)、和 1-[1,3,5-三甲基-吡唑-4-基],2-[2-甲基-5-苯基-1-噻吩-3-基]全氟环戊烯（4a）的合成。详细研究了这些化合物的光学和电化学性质，如光致变色、光致变色环化-环氧化动力学、荧光和电化学性质。结果表明，所有这些化合物都具有良好的光致变色性、较高的环化量子产率和较强的荧光。经测定，它们的环化-环oreversion 过程是零阶到一阶反应。二芳香烃 1a-4a 的氧化分别在 0.73、1.11、0.79 和 1.03 V 的电压下开始。此外，还发现在末端苯基环的不同位置引入电子致性甲氧基会对这些光学和电化学性质产生强烈影响。
• The effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a methoxy group
  作者：Shouzhi Pu、Congbin Fan、Wenjuan Miao、Gang Liu

  DOI：10.1016/j.dyepig.2009.06.018

  日期：2010.1

  coefficients of both of the open-ring and closed-ring isomers decreased when the methoxy group was attached at any of the three positions on the terminal benzene ring whereas the cycloreversion quantum yield gradually increased in going from the para- to meta- to the ortho-position of substitution. Oxidation waves were clearly observed at 0.55, 0.74 and 0.58 V from cyclic voltammograms for some compounds

  合成了三个在一个末端苯环的对位，间位或邻位带有甲氧基的不对称异构体光致变色二硫杂环丁烷，并对其光学和电化学性质进行了研究。每种化合物在溶液中和在PMMA膜中均显示出高的光反应敏感性，并起着荧光光开关的作用。当甲氧基连接在末端苯环的三个位置中的任何一个上时，开环和闭环异构体的摩尔吸收系数均降低，而环还原量子产率从对位到间位逐渐增加。到邻取代位置。从循环伏安图可以清楚地在0.55、0.74和0.58 V处观察到某些化合物的氧化波，而在这些电压下则看不到其他化合物。
• Polarization holographic optical recording based on a new photochromic diarylethene compound
  作者：Hui Li、Shouzhi Pu、Gang Liu、Weijun Liu、Baoli Yao

  DOI：10.1007/s11458-010-0101-0

  日期：2010.6

  A new unsymmetrical photochromic diarylethene, namely1-[2-methyl-5-(p-N,N-dimethylaminophenyl)-3-thienyl]-2-[2-methyl-5-(3-methoxylphenyl)-3-thienyl] perfluorocyclopentene (1a), was synthesized. The compound showed good photochromism, high sensitivity and remarkable fatigue-resistance both in solution and in poly(methyl methacrylate) (PMMA) matrix with UV/Vis light irradiation. The absorption maximum of its closed-ring isomer was observed at 624 nm in PMMA amorphous film. It is a nice match for the wavelength of the recording laser (633 nm). Using this target compound as recording medium, four types of polarization holographic optical recordings were performed successfully using a He-Ne laser. The results showed that only the orthogonal circular polarization recording could obtain a hologram with high diffraction efficiency and high signal-to noise-ratio. With multiplexing recording technology, three types of polarization multiplexing holographic optical recordings, including angular multiplexing, polarization multiplexing, and angular plus polarization multiplexing holographic recording, were also carried out perfectly based on its photoinduced anisotropic phenomenon accompanying the photochromic reaction by photoirradiation. The results demonstrate that the multiplexing recording technology is an effective method to improve recording capacity when using diarylethene 1 as recording medium.

  合成了一种新的非对称光致变色二芳基烯，即 1-[2-甲基-5-（对-N,N-二甲基氨基苯基）-3-噻吩基]-2-[2-甲基-5-（3-甲氧基苯基）-3-噻吩基]全氟环戊烯（1a）。该化合物在溶液中和聚甲基丙烯酸甲酯（PMMA）基体中，在紫外/可见光照射下均表现出良好的光致变色性、高灵敏度和显著的抗疲劳性。在聚甲基丙烯酸甲酯（PMMA）无定形薄膜中，其闭环异构体的吸收最大值出现在 624 纳米波长处。这与记录激光的波长（633 nm）非常吻合。以这种目标化合物为记录介质，使用氦氖激光成功地进行了四种偏振全息光学记录。结果表明，只有正交圆偏振记录才能获得高衍射效率和高信噪比的全息图。在复用记录技术的基础上，还利用光照射伴随光致变色反应产生的光诱导各向异性现象，完美地实现了三种偏振复用全息光学记录，包括角度复用、偏振复用和角度加偏振复用全息记录。结果表明，复用记录技术是使用二元蒽 1 作为记录介质时提高记录容量的有效方法。
• Synthesis and the effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a pyrrole unit
  作者：Gang Liu、Shouzhi Pu、Xiaomei Wang

  DOI：10.1016/j.jphotochem.2010.07.001

  日期：2010.8

  moiety were synthesized, and the structures of two isomeric compounds were determined by single-crystal X-ray diffraction analysis. The properties of these compounds, including photochromism, fluorescence and electrochemical properties of these diarylethenes were also investigated systematically. Each of the four diarylethene derivatives exhibited good photochromism and functioned as an effective fluorescent

  合成了四个带有吡咯部分的不对称二芳烃，并通过单晶X射线衍射分析确定了两种异构体的结构。还系统地研究了这些化合物的性质，包括这些二芳烃的光致变色，荧光和电化学性质。四种二芳基乙烯衍生物中的每一种均表现出良好的光致变色性，并且在溶液和PMMA膜中均起有效的荧光光开关作用。当在末端苯环的三个位置上的任何一个上连接甲氧基时，最大吸收率，环化和环还原的量子产率以及开环异构体的荧光量子产率增加，而发射峰明显减少。与带有吡唑部分的类似二芳烃相比，吡咯部分的引入可以增加吸收最大值，并显着降低环回复量子产率。循环伏安图证实，甲氧基及其取代位置可有效调节这些二芳基乙烯衍生物的电化学行为。