1,2-二(2-甲基-5-苯基噻吩-3-基)环戊-1-烯 | 473463-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 1,2-二(2-甲基-5-苯基噻吩-3-基)环戊-1-烯
• 英文名称: 1,2-bis(2'-methyl-5'-phenylthien-3'-yl)cyclopentene
• 英文别名: 1,2-bis(5-phenyl-2-methylthien-3-yl)cyclopentene；1,2-Bis(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-ene；2-methyl-3-[2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-5-phenylthiophene
• CAS: 473463-85-3
• 化学式: C₂₇H₂₄S₂
• 分子量: 412.62
• InChiKey: ADDVFVWWTKZKOH-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  570.7±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-二(2-甲基-5-苯基噻吩-3-基)环戊-1-烯 以 正己烷 为溶剂， 反应 1.25h， 生成 1,2-Dimethyl-4,14-diphenyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraene
  参考文献：
  名称：

  Functionalisation of MoS₂ 2D layers with diarylethene molecules

  摘要：

  用光开关二芳基乙烯衍生物共价和静电地功能化的MoS₂片屑。

  DOI：

  10.1039/d1tc01133b
• 作为产物：
  描述：

  (9aR,9bR)-9a,9b-Dimethyl-2,8-diphenyl-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trindene 生成 1,2-二(2-甲基-5-苯基噻吩-3-基)环戊-1-烯
  参考文献：
  名称：

  An Optical and Theoretical Investigation of the Ultrafast Dynamics of a Bisthienylethene-Based Photochromic Switch

  摘要：

  The switching behavior of 1,2-bis(5-phenyl-2-methylthien-3-yl)cyclopentene is studied by means of polarization selective nonlinear optical spectroscopy and time-dependent density functional theory. The combined information from the observed population and orientational dynamics together with the results of theoretical calculations show that on a subpicosecond time scale rapid mixing and relaxation of electronic states occur, before switching takes place. Such preswitching dynamics was not studied in detail in these systems before. Then, the switching process itself occurs by the formation of a C-C bond in the central cyclopentene ring with a time constant of 4.2 ps. Driven by the ring closure, the side groups of the switch molecules rotate to a nearly coplanar conformation with a time constant of about 8 ps. The switching process is completed by relaxation of the vibrationally hot ground state of the closed form of the molecule to thermal equilibrium.

  DOI：

  10.1021/jp020903+
• 作为试剂：
  描述：

  氧气 在 zinc tetraphenylporphyrin 、 1,2-二(2-甲基-5-苯基噻吩-3-基)环戊-1-烯 作用下， 以 甲苯 为溶剂， 生成 oxygen
  参考文献：
  名称：

  使用二芳基乙烯光致变色开关对单线态氧气产生的可逆光化学控制

  摘要：

  在包含二芳基乙烯光致变色开关和卟啉光敏剂的双组分系统中，通过不同波长的选择性照射，证明了对单线态氧产生的可逆无创控制。当二芳基乙烯单元为无色开放形式时，观察到光敏剂有效产生单线态氧。当二芳基乙烯转化为闭合形式时，没有观察到单线态氧的产生。用可见光 (>470 nm) 照射封闭形式导致卟啉敏化剂的单线态氧生成能力完全恢复。

  DOI：

  10.1021/ja4122473

文献信息

• General and highly efficient fluorinated-N-heterocyclic carbene–based catalysts for the palladium-catalyzed Suzuki–Miyaura reaction
  作者：Taoping Liu、Xiaoming Zhao、Qilong Shen、Long Lu

  DOI：10.1016/j.tet.2012.05.068

  日期：2012.8

  acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki–Miyaura reaction of aryl bromides and chlorides with 0.01–0.1 mol % loading if the temperature was raised at refluxed THF/H2O.

  据报道，一种通用且高效的三氟甲基化-N-杂环卡宾（NHC）基催化剂可用于钯催化的Suzuki-Miyaura反应。在催化剂的存在下，未活化的芳基氯和三氟甲磺酸与芳基硼酸的反应在室温下发生，收率好至极好（63-98％）。此外，由Pd（OAc）2 /咪唑鎓盐6a的组合产生的催化剂不仅对于杂芳基硼酸与芳基卤化物和杂芳基卤化物的偶联有效，而且对其他杂芳基卤化物和杂芳基硼酸的偶联有效。最后，如果温度在回流的THF / H 2 O上升高，则该催化剂对于0.01-0.1 mol％负载量的芳基溴化物和氯化物的Suzuki-Miyaura反应非常有效。
• Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism
  作者：Hiroyasu Nishi、Tomoko Namari、Seiya Kobatake

  DOI：10.1039/c1jm12707a

  日期：——

  Photochromic polymers with various diarylethene derivatives were synthesized by a conventional radical polymerization of styrene derivatives having diarylethene chromophores as the pendant. All the polymers exhibited reversible photochromism in the film as well as in solution, while the photocyclization conversion in the film decreased in comparison with that in solution because of a restriction of the conformational structure in the solid state. Although the photocyclization and photocycloreversion quantum yields at the initial stage of the reactions in the film were comparable to those in solution, the apparent cycloreversion quantum yield decreased along with the reaction, which is derived from a distribution of the quantum yields in the solid state. Finally, the photochromic terpolymers consisting of three diarylethene monomers which show photochromism changing color to cyan, magenta, and yellow were synthesized. The terpolymers were demonstrated to show bright colors including black, green, red, and blue both in solution and in the solid state by selective bleaching processes. Such multicolor photochromic polymers composed of diarylethene derivatives have a potential for rewritable photochromic display devices.

  合成了具有多种二芳基乙烯衍生物的光敏聚合物，这是通过对具有二芳基乙烯色团作为侧链的苯乙烯衍生物进行常规自由基聚合获得的。所有聚合物在薄膜和溶液中均表现出可逆的光致变色特性。然而，由于固态中构象结构的限制，薄膜中的光环化转化率与溶液中相比有所降低。尽管在反应初期，薄膜中的光环化和光环反转量子产率与溶液中相当，但随着反应的进行，明显的环反转量子产率下降，这源于固态中量子产率的分布。最后，合成了由三种二芳基乙烯单体组成的光敏三元聚合物，其光致变色改变为青色、品红色和黄色。这些三元聚合物通过选择性漂白过程在溶液和固态中表现出明亮的颜色，包括黑色、绿色、红色和蓝色。由二芳基乙烯衍生物组成的这种多色光敏聚合物在可重写的光致变色显示设备中具有潜在应用。
• 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。
• LIGHT-ACTIVATED ACTUATOR ELEMENT
  申请人：Irie Masahiro

  公开号：US20100016608A1

  公开（公告）日：2010-01-21

  Disclosed is light-driven actuator element characterized in that, inter alia, it can be reduced to micrometer size, is rapidly responsive, and reversibly changes to enable repeated use. The light-driven actuator element includes a crystal of diarylethene compound which changes shape upon photoisomerization (e.g., the compound of Structural Formula (I) below, where R 1 represents a hydrogen atom or methyl group and R 2 represents a methyl group). The element can be a rod-shaped or plate-like microcrystal having a size on the order of micrometer. The element bends (or contracts) on irradiation with ultraviolet light and expands to return to the original size on irradiation with visible light.

  揭示了一种光驱动致动器元件，其特点在于，它可以缩小到微米尺寸，响应迅速，并可反复变化以实现重复使用。光驱动致动器元件包括一种二芳基乙烯化合物的晶体，该化合物在光异构化时改变形状（例如，下面的结构式（I）中的化合物，其中R1代表氢原子或甲基基团，R2代表甲基基团）。该元件可以是杆状或板状微晶，尺寸在微米级别。该元件在紫外光照射下弯曲（或收缩），在可见光照射下扩展以返回原始尺寸。