1,2-bis[5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl]cyclopentene | 593260-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis[5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl]cyclopentene
• 英文别名: 1,2-bis(5-(4-methoxyphenyl)-2-methylthien-3-yl)cyclopent-1-ene；1,2-bis[2-methyl-5-(4-methoxyphenylthien)-3-yl]cyclopentene；1,2-bis[5-(4-methoxyphenyl)-2-methylthien-3-yl]cyclopentene；5-(4-Methoxyphenyl)-3-[2-[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-2-methylthiophene
• CAS: 593260-84-5
• 化学式: C₂₉H₂₈O₂S₂
• 分子量: 472.672
• InChiKey: BDDZJTQTRNVVNC-UHFFFAOYSA-N

物化性质

• 沸点：
  621.6±55.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis[5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl]cyclopentene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以100%的产率得到4,4'-(4,4'-(cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-4,2-diyl))diphenol
  参考文献：
  名称：

  Optic and proton dual-control of the fluorescence of Rhodamine based on photochromic diarylethene: mimicking the performance of an integrated logic gate

  摘要：

  A proton and optic dual-responsive fluorescence switch dyad which contains Rhodamine and photochromic diarylethene has been designed and an integrated logic circuit at the molecular level has been proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.093
• 作为产物：
  描述：

  1,2-双(5-氯-2-甲基噻吩-3-基)环戊-1-烯 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1,2-bis[5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl]cyclopentene
  参考文献：
  名称：

  对称和非对称双联噻吩基环戊烯的合成

  摘要：

  双芳烃具有独特的结构特性，这使它们能够在光致变色领域中找到广泛的应用。如今，双噻吩基环戊烯（BTC）代表了这些化合物中最流行的亚家族，被广泛用作P型发色团。这份小型回顾总结了合成对称和非对称BTC的主要策略。另外，提请注意由单取代实现的脱对称，尽管它可以是非常有利的，但是它不经常使用。一些作者的最新结果对此提供了支持。

  DOI：

  10.1002/chem.201301645

文献信息

• Photochromic Properties of Perhydro- and Perfluorodithienylcyclopentene Molecular Switches
  作者：Jaap J. D. de Jong、Linda N. Lucas、Ralph Hania、Audrius Pugzlys、Richard M. Kellogg、Ben L. Feringa、Koos Duppen、Jan H. van Esch

  DOI：10.1002/ejoc.200200719

  日期：2003.5

  Various substituted phenylthienyl perhydro- and perfluorocyclopentenes have been synthesized in order to compare their spectroscopic and photochromic properties. The difference in the electron densities of the central cyclopentene moieties in the perhydrocyclopentene and perfluorocyclopentene molecular switches has only a small effect on the absorption maxima of the electronic spectra, but causes some

  为了比较它们的光谱和光致变色特性，已经合成了各种取代的苯基噻吩基全氢和全氟环戊烯。全氢环戊烯和全氟环戊烯分子开关中中心环戊烯部分的电子密度差异对电子光谱的吸收最大值只有很小的影响，但会引起取代基和溶剂致变色效应的一些细微变化。光致变色行为非常相似，两种类型的开关都结合了出色的量子产率 (0.6) 和高度的光转换 (> 0.85)。主要区别在于全氢环戊烯分子开关的光化学和热稳定性较低。得出的结论是，在大多数研究中，全氢环戊烯是全氟环戊烯的绝佳替代品，而全氟环戊烯可能更适合数据存储等应用，这些应用关键取决于抗疲劳性和热稳定性。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)。
• 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。
• Functionalization of a Simple Dithienylethene via Palladium-Catalyzed Regioselective Direct Arylation
  作者：Hiroki Kamiya、Shuichi Yanagisawa、Satoru Hiroto、Kenichiro Itami、Hiroshi Shinokubo

  DOI：10.1021/ol2026069

  日期：2011.12.16

  The direct arylation on the thienyl groups of a diarylethene with various aryl iodides efficiently provided arylated dithienylethenes under palladium catalysis. Unsymmetrically substituted dithienylethenes were also synthesized by this protocol. This procedure allows a rapid access to a variety of aryl-substituted dithienylethenes from a single substrate of a simple dithienylethene.

  在钯催化下，二芳基乙烯的噻吩基与各种芳基碘化物的直接芳基化有效地提供了芳基化的二噻吩基乙烯。该协议还合成了不对称取代的二噻吩基乙烯。该方法允许从简单的二噻吩基乙烯的单个底物快速获得各种芳基取代的二噻吩基乙烯。
• Oxidative Electrochemical Switching in Dithienylcyclopentenes, Part 1: Effect of Electronic Perturbation on the Efficiency and Direction of Molecular Switching
  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.200500162

  日期：2005.10.21

  clopentenes are reported. The large effect of variation in the central cyclopentene moieties on the redox properties of the dithienylcyclopentenes is in striking contrast to the minor effect on their photochemical properties. The electronic properties of the oxidised compounds in the +1 and +2 oxidation state are reported, and the possibility of electrochemical cyclisation and cycloreversion were explored

  报道了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。中心环戊烯部分的变化对二噻吩基环戊烯的氧化还原性质的大影响与对它们的光化学性质的较小影响形成鲜明对比。报告了在+1和+2氧化态下氧化化合物的电子性质，并通过UV / Vis光谱电化学探索了电化学环化和环还原的可能性。发现电化学转换的效率既取决于中央环戊烯单元，也取决于噻吩基环的C 5处的取代基的性质。对于六氢环戊烯基化合物，观察到开环形式的氧化性闭环，而对于六氟环戊烯基化合物，则观察到闭环形式的氧化性开环。然而，引入电活性基团例如甲氧基苯基允许在六氟化合物中发生氧化性闭环。检查了电解质，溶剂和温度对光谱电化学性质的影响，发现转换过程对所用溶剂/电解质体系的供体性质敏感。另外，观察到双键封闭形式的热活化可逆异构化。用于电化学开环和闭环的驱动力似乎取决于双环开环和闭环状态的相对稳定性。这项研究深入了解了决定环化方向的因素。
• Multimodal fluorescence modulation using molecular photoswitches and upconverting nanoparticles
  作者：Carl-Johan Carling、John-Christopher Boyer、Neil R. Branda

  DOI：10.1039/c2ob25368b

  日期：——

  The intensity and colour of the light emitted from upconverting nanoparticles is controlled by the state of photoresponsive dithienylethene ligands decorated onto the surface of the nanoparticles. By selectively activating one or both ligands in a mixed, 3-component system, a multimodal read-out of the emitted light is achieved.

  上转换纳米粒子发出的光的强度和颜色由装饰在纳米粒子表面的光响应二噻吩乙烯配体的状态控制。通过选择性地激活混合的三组分系统中的一个或两个配体，可以实现对发射光的多模式读取。