1,2-bis(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,2-bis(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-ene
• 英文别名: 1,2-bis(2-methyl-1-benzothiophene-3-yl)cyclopentene；1,2-bis(2-methyl-1-benzothiophen-3-yl)cyclopentene；2-methyl-3-[2-(2-methyl-1-benzothiophen-3-yl)cyclopenten-1-yl]-1-benzothiophene
• 化学式: C₂₃H₂₀S₂
• 分子量: 360.544
• InChiKey: YHRUJCHVTABZTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 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-bis(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-ene 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 甲醇 、 硝基苯 为溶剂， 反应 3.0h， 生成 1,2-bis(6-carboxy-2-methylbenzo[b]thiophen-3-yl)cyclopent-1-ene
  参考文献：
  名称：

  基于1,2-双(2-甲基苯并[b]噻吩-3-基)环戊-1-烯的多层聚合物结构的合成与研究

  摘要：

  1,2-双(2-甲基苯并[b]噻吩-3-基)环戊-1-烯的酰化得到对称和不对称的1,2-二杂芳基乙烯，它们作为光致变色记录介质的光敏组分用于光学读取/写存储。研究了在波导多层系统的含二杂芳基乙烯的光致变色光折变层中形成光致衍射光栅。

  DOI：

  10.1007/s11172-011-0390-6
• 作为产物：
  描述：

  3-溴-2-甲基-苯并[b]噻吩 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 24.75h， 生成 1,2-bis(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-ene
  参考文献：
  名称：

  Photochromism and fluorescence properties of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes

  摘要：

  Three 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes with different alkyl chain lengths (methyl, ethyl, and propyl) at the reactive carbons were synthesized, and their photophysical properties were compared with those of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perfluorocyclopentenes. The structures of the perhydrocyclopentenes were analyzed by X-ray crystallography, and their cyclization/cycloreversion reaction and fluorescence quantum yields, and fluorescence lifetimes were measured by steady-state spectroscopy and the time-correlated single photon counting method, respectively. From these results, we found the following three differences between perhydrocyclopentenes and perfluorocyclopentenes. (1) For the closed-ring isomers, the absorption bands of the perhydrocyclopentenes (around 450 nm) shifted to a shorter wavelength than those of the perfluorocyclopentenes (around 530 nm) because of the acceptor nature of the perfluorocyclopentene moiety. (2) The cyclization/cycloreversion quantum yields of the perhydrocyclopentenes were slightly larger than those of the perfluorocyclopentenes in hexane. (3) Interestingly, the fluorescence of both the open- and closed-ring isomers was observed only for the perhydrocyclopentenes, and the lifetimes of the closed-ring isomers were estimated to be <30 ps. The fluorescence of the closed-ring isomers of the perhydrocyclopentenes was mainly due to the suppression of nonradiative deactivation from the excited state directly to the ground state compared with the perfluorocyclopentenes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2014.04.007

文献信息

• Synthesis and studies of symmetric dibenzothienylcyclopentenes
  作者：Vasily A. Migulin、Michael M. Krayushkin、Valery A. Barachevsky、Olga I. Kobeleva、Valentin V. Novikov、Konstantin A. Lyssenko

  DOI：10.1016/j.tet.2014.12.036

  日期：2015.1

  displayed photochromism in the single crystal. High resolution X-ray diffraction showed that intermolecular S⋯π and S⋯H contacts kept two benzothiophene rings together in the molecule, hence decreasing the distance between the two reactive centers responsible for the photocyclization reaction. DFT calculations of the isolated molecules appeared to be in good agreement with the obtained XRD data, and therefore

  各种对称的5,5'-取代的二苯并[ b]噻吩基环戊烯由相应的二溴化物合成，并形成新的C–C，C–N，C–O，C–Si和C–I键。在溶液和固态下，系统地研究了引入的取代基对所得化合物的光致变色性能的影响。通过NMR光谱法测定溶液中反平行和平行构象异构体的比例。5,5'-二苯氧基取代的系列中只有一种化合物在单晶中显示出光致变色现象。高分辨率X射线衍射表明，分子间S⋯π和S⋯H接触将分子中的两个苯并噻吩环保持在一起，从而减小了负责光环化反应的两个反应中心之间的距离。分离出的分子的DFT计算似乎与获得的XRD数据非常吻合，
• Photochromic monomers, photochromic polymers based on the same, photochromic recording media comprising the photochromic polymers, and 3D read/write optical memory comprising the recording media
  申请人：Dunaev Alexandr Alexandrovich

  公开号：US20060079653A1

  公开（公告）日：2006-04-13

  Photochromic monomers and methods for preparing these photochromic monomers, photochromic polymers based on these photochromic monomers and methods for preparing these photochromic polymers, as well as the use of these photochromic polymers in a polymer binder as a two-photon recording medium for an optical 3D memory and photoswitches of optical signals are disclosed. The materials exhibit thermally irreversible photochromic transformations and other properties enabling the use of the photochromic polymers in an optical two-photon read/write memory.

  本发明涉及光致变色单体及其制备方法，基于这些光致变色单体的光致变色聚合物及其制备方法，以及在聚合物粘合剂中使用这些光致变色聚合物作为光学3D存储的双光子记录介质和光信号的光开关。这些材料表现出热不可逆的光致变色转换和其他性质，使得光致变色聚合物可以用于光学双光子读写存储器。
• Synthesis and the structure of 1,2-bis(6-acetyl-2-methylbenzo[b]thiophen-3-yl)cyclopentene
  作者：M. M. Krayushkin、L. G. Vorontsova、V. N. Yarovenko、I. V. Zavarzin、V. N. Bulgakova、Z. A. Starikova、V. A. Barachevskii

  DOI：10.1007/s11172-008-0342-y

  日期：2008.11

  New 1,2-dihetarylethene containing two 6-acetyl-2-methylbenzo[b]thiophene moieties linked by the cyclopentene bridge was synthesized. In a toluene solution, this compound exhibits photochromic properties. The X-ray diffraction study showed that the crystal structure also has properties characteristic of photochromic compounds, viz., the anti-parallel conformation of the molecule and the distance between the reaction centers equal to 3.729 Å.

  合成了一种新的1,2-二亚甲基乙烯，其中包含两个由环戊烯桥连接的6-乙酰基-2-甲基苯并[b]噻吩部分。在甲苯溶液中，该化合物表现出光致变色特性。X射线衍射研究表明，该晶体的结构也具有光致变色化合物的特性，即分子的反平行构象和反应中心之间的距离为3.729 Å。
• Lithographic printing plate precursor and lithographic printing method
  申请人：Fuji Photo Film Co., Ltd.

  公开号：EP1754614A1

  公开（公告）日：2007-02-21

  The invention is directed to a lithographic printing plate precursor comprising a support and an image-recording layer, wherein the image-recording layer comprises (1) an infrared absorber and (2) a photochromic compound. The invention is also directed to a method of plate making and a lithographic printing method, each method using the lithographic printing plate precursor.

  本发明涉及一种平版印刷板前体，包括一个支撑物和一个图像记录层，其中图像记录层包括(1)红外线吸收剂和(2)光致变色化合物。本发明还涉及一种制版方法和一种平版印刷方法，每种方法都使用平版印刷板前体。
• Photocontrolled photochromic electroluminescent and electroconductive polymers for photonics
  申请人：Alfimov Vladimirovich Mikhail

  公开号：US20060091364A1

  公开（公告）日：2006-05-04

  The invention relates to photochromic monomers based on benzothiophenes and a method for preparing them, and to photochromic polymers-polyazomethines that are reversibly photocontrollable due to the introduction of photochromic fragments from the class of dihetarylethenes into their structure. The invention provides photochromic photocontrollable polymers for the creation of new information technologies.

  本发明涉及基于苯并噻吩的光致变色单体及其制备方法，以及由于在其结构中引入了二苯乙烯类的光致变色片段而具有可逆光控性的光致变色聚合物--聚氮甲烷。本发明为创造新的信息技术提供了光致变色可控聚合物。