1,2-bis[5'-(4''-acetylthio)-2'-methylthien-3'-yl]cyclopentene | 872858-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: 1,2-bis[5'-(4''-acetylthio)-2'-methylthien-3'-yl]cyclopentene
• 英文别名: S-[4-[4-[2-[5-(4-acetylsulfanylphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-5-methylthiophen-2-yl]phenyl] ethanethioate
• CAS: 872858-24-7
• 化学式: C₃₁H₂₈O₂S₄
• 分子量: 560.826
• InChiKey: ASDWVDHGZADWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis[5'-(4''-acetylthio)-2'-methylthien-3'-yl]cyclopentene 以 乙腈 为溶剂， 生成 S-[4-[14-(4-acetylsulfanylphenyl)-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]phenyl] ethanethioate
  参考文献：
  名称：

  Raman scattering and FT-IR spectroscopic studies on dithienylethene switches—towards non-destructive optical readout

  摘要：

  探索了基于二噻二烯单元的光变记忆材料的非破坏性读出，采用红外光谱和拉曼散射。研究了一系列典型的C5取代的噻吩六氢和六氟环戊烯基光变材料，以探讨取代效应及其在多组分记忆材料开发中的潜在应用。还研究了沉积方法对含有光变二噻二烯环戊烯开关固态材料光化学的影响。发现从开态转化为闭态的光转化率较低，而从闭态转化为开态的环开过程则是完全的。此现象被认为是由于内过滤效应而非构象现象。为中央的二噻二烯核心分配了特征振动带，并对氢化和氟化开关的振动光谱性质进行了比较。这些数据使得能够确定固态下可实现的光转化率，以及对沉积方法对光转化影响的某种评估。通过在不导致光化学环开过程的波长下监测开闭态之间绝对拉曼散射强度的巨大差异，证明了拉曼光谱作为实现非破坏性光学读出的潜力。

  DOI：

  10.1039/b603914f
• 作为产物：
  描述：

  1,2-双(5-氯-2-甲基噻吩-3-基)环戊-1-烯 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 5.0h， 生成 1,2-bis[5'-(4''-acetylthio)-2'-methylthien-3'-yl]cyclopentene
  参考文献：
  名称：

  Molecular Switches Get Wired: Synthesis of Diarylethenes Containing One or Two Sulphurs

  摘要：

  Two series of novel diarylethenes, the first containing one and the second two acetyl protected thiol groups, were synthesised in two and three steps from an easily available known intermediate. Newly synthesised compounds present ideal examples of model substrates for photochromic studies on metal surfaces.

  DOI：

  10.1080/15421400590946398

文献信息

• Oxidative Electrochemical Switching in Dithienylcyclopentenes, Part 2: Effect of Substitution and Asymmetry on the Efficiency and Direction of Molecular Switching and Redox Stability
  作者：Wesley R. Browne、Jaap J. D. de Jong、Tibor Kudernac、Martin Walko、Linda N. Lucas、Kingo Uchida、Jan H. van Esch、Ben L. Feringa

  DOI：10.1002/chem.200500163

  日期：2005.10.21

  The electrochemical and spectroelectrochemical properties of a series of C5-substituted dithienylhexahydro- and dithienylhexafluorocyclopentenes are reported. The effect of substitution at C5 of the thienyl moiety on the redox properties is quite dramatic, in contrast to the effect on their photochemical properties. The efficiency of electrochemical switching is dependent both on the central cyclopentene

  报道了一系列C 5-取代的二噻吩基六氢和二噻吩基六氟环戊烯的电化学和光谱电化学性质。与对其光化学性质的影响相反，噻吩基部分在C 5处的取代对氧化还原性质的影响是非常显着的。电化学转换的效率既取决于中央环戊烯单元，又取决于取代基的性质，其中供电子部分有利于氧化电化学闭环，反之亦然。研究了不对称取代的二噻吩基环戊烯，以更详细地探讨闭环过程。结果表明，电化学诱导的闭环是通过开放形式的单阳离子发生的。在噻吩基环的C5存在电活性基团的情况下（例如，
• Molecular Switches Get Wired: Synthesis of Diarylethenes Containing One or Two Sulphurs
  作者：T. Kudernac、J. J. De Jong、J. Van Esch、B. L. Feringa、D. Dulić、S. J. Van Der Molen、B. J. Van Wees

  DOI：10.1080/15421400590946398

  日期：2005.5.1

  Two series of novel diarylethenes, the first containing one and the second two acetyl protected thiol groups, were synthesised in two and three steps from an easily available known intermediate. Newly synthesised compounds present ideal examples of model substrates for photochromic studies on metal surfaces.
• Raman scattering and FT-IR spectroscopic studies on dithienylethene switches—towards non-destructive optical readout
  作者：Jaap J. D. de Jong、Wesley R. Browne、Martin Walko、Linda N. Lucas、Lindsay J. Barrett、John J. McGarvey、Jan H. van Esch、Ben L. Feringa

  DOI：10.1039/b603914f

  日期：——

  The non-destructive readout of photochromic memory materials based on the dithienylethene unit both by IR spectroscopy and Raman scattering is explored. A representative series of C5-substituted thienyl hexahydro- and hexafluoro-cyclopentene based photochromes was investigated to explore the effect and potential usefulness of substitution for the development of multicomponent memory materials. The effect of the deposition method on the photochemistry of solid materials containing photochromic dithienylcyclopentene switches was also explored. Photoconversion in the solid state to the closed form was found to be low when starting from the open form, but, in contrast, ring opening to the open state from the closed form was found to be complete. The effect was found to be due to inner filter rather than conformational phenomena. Characteristic vibrational bands for the central dithienyl core are assigned and a comparison made of the vibrational spectroscopic properties of the perhydro- and perfluoro switches. The data enable the determination of the photoconversion achievable in the solid state as well as some assessment of the influence of the deposition method on the photoconversion. The potential of Raman spectroscopy as a method of achieving non-destructive optical readout is demonstrated through the large differences in absolute Raman scattering intensity between the open and closed states, when monitored at wavelengths which do not result in photochemical ring opening.

  探索了基于二噻二烯单元的光变记忆材料的非破坏性读出，采用红外光谱和拉曼散射。研究了一系列典型的C5取代的噻吩六氢和六氟环戊烯基光变材料，以探讨取代效应及其在多组分记忆材料开发中的潜在应用。还研究了沉积方法对含有光变二噻二烯环戊烯开关固态材料光化学的影响。发现从开态转化为闭态的光转化率较低，而从闭态转化为开态的环开过程则是完全的。此现象被认为是由于内过滤效应而非构象现象。为中央的二噻二烯核心分配了特征振动带，并对氢化和氟化开关的振动光谱性质进行了比较。这些数据使得能够确定固态下可实现的光转化率，以及对沉积方法对光转化影响的某种评估。通过在不导致光化学环开过程的波长下监测开闭态之间绝对拉曼散射强度的巨大差异，证明了拉曼光谱作为实现非破坏性光学读出的潜力。