2,3-bis(2-methylbenzothiophen-3-yl)thiophene | 1151790-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,3-bis(2-methylbenzothiophen-3-yl)thiophene
• 英文别名: 2,3-bis(2-methyl-benzo[b]thiophene-3-yl)thiophene；2,3-bis(2-methylbenzo[b]thiophen-3-yl)thiophene；2-methyl-3-[2-(2-methyl-1-benzothiophen-3-yl)thiophen-3-yl]-1-benzothiophene
• CAS: 1151790-22-5
• 化学式: C₂₂H₁₆S₃
• 分子量: 376.567
• InChiKey: WFAHYMQEACVWLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-bis(2-methylbenzothiophen-3-yl)thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以96%的产率得到
  参考文献：
  名称：

  开启荧光光致变色二磺酰基芳基噻吩：砜基团对荧光和转化的影响

  摘要：

  在室温下，通过间氯过氧苯甲酸对苯并噻吩基团进行选择性硫氧化，合成了一系列含砜基的二芳基噻吩，并对其光物理化学性质进行了研究。这些化合物在连续的紫外线（UV）和可见光照射下表现出良好的光致变色行为和良好的疲劳性能。闭环形式在紫外线激发下会发出荧光，并且荧光的波长取决于取代基。化合物2 - 5显示出高的转化率，达到95％的化合物5，在紫外线辐射下的苯甲酰基衍生物。认为这种高转化率是由于与开环反应相比，开环反应的量子产率较低。

  DOI：

  10.1002/bkcs.11597
• 作为产物：
  描述：

  2,3-二溴噻吩 、 dibutyl(2-methyl-benzo[b]thiophen-3-yl) borane 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 2,3-bis(2-methylbenzothiophen-3-yl)thiophene
  参考文献：
  名称：

  The considerable photostability improvement of photochromic terarylene by sulfone group

  摘要：

  Photochromic terarylene derivative 4 which has a sulfone group at the upper benzothiophene ring is readily synthesized using Suzuki coupling reaction. It exhibits good photochromic properties. Interestingly, the closed form of the compound 4 shows a good photostability as well as a thermal stability compared with its reduced analog 3, that provides a method to enhance the photostability of versatile photochromic terarylenes under UV. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.028

文献信息

• Photoswitchable fluorescent diarylethene in a turn-on mode for live cell imaging
  作者：Shi-Chong Pang、Hyesook Hyun、Seungah Lee、Daeun Jang、Min Jae Lee、Seong Ho Kang、Kwang-Hyun Ahn

  DOI：10.1039/c2cc30738c

  日期：——

  A new diarylethene-derived photochromic compound, with little cytotoxicity, plasma membrane-permeability, and efficient photoswitchability in cells upon alternative UV and visible light irradiation, was synthesized and applied to live cell imaging.

  合成了一种新的二芳基乙烯衍生的光致变色化合物，该化合物具有很小的细胞毒性、质膜渗透性以及在交替紫外光和可见光照射下细胞内的高效光切换性，并将其应用于活细胞成像。
• The effect of a “push—pull” structure on the turn-on fluorescence of photochromic thio-ketone type diarylethenes
  作者：Shichong Pang、Daeun Jang、Woo Sun Lee、Hyeok-Mo Kang、Seung-Ju Hong、Sung Kwan Hwang、Kwang-Hyun Ahn

  DOI：10.1039/c4pp00320a

  日期：2015.4

  a series of diarylethene compounds with a thiophene bridging unit have been synthesized to investigate the relationship between molecular structure and photochromic properties. In particular, the fluorescence properties related to compound 1 were investigated. The results showed that a six-membered ring carrying an electron-donating sulfur atom and an electron-withdrawing carbonyl group is necessary to form a “push–pull” system for the fluorescence of 1.

  合成了一系列带有噻吩桥联单元的二芳基乙烯化合物，以研究分子结构与光致变色性能之间的关系。特别是，研究了与化合物1相关的荧光特性。结果表明，带有给电子硫原子和吸电子羰基的六元环对于形成1的荧光“推拉”体系是必要的。
• Photochromic diarylethene-containing coordination compounds and the production thereof
  申请人：Yam Wing-Wah Vivian

  公开号：US20070057240A1

  公开（公告）日：2007-03-15

  Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower energy absorption bands characteristic of the coordination compounds, through which the excitation wavelengths for the photocyclization can be extended from λ≦340 nm to wavelengths beyond 470 nm. Switching of the luminescence properties of the compounds has also been achieved through photochromic reactions.

  本文介绍了含有二芳基乙烯基配体及其配位化合物。这些配体在紫外激发下表现出光致变色性质，而配位化合物则在紫外区域和较低能量吸收带中表现出光致变色性质，通过这些能够将光化学反应的激发波长从λ≦340 nm延伸至超过470 nm的波长。此外，还通过光致变色反应实现了化合物发光性质的切换。
• Photochromic diarylethene containing coordination compounds and the production thereof
  申请人：Yam Vivian Wing-Wah

  公开号：US20100137596A1

  公开（公告）日：2010-06-03

  Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower energy absorption bands characteristic of the coordination compounds, through which the excitation wavelengths for the photocyclization can be extended from λ≦340 nm to wavelengths beyond 470 nm. Switching of the luminescence properties of the compounds has also been achieved through photochromic reactions.

  本文描述了含有二芳基乙烯基配体及其配位化合物。这些配体在紫外激发下表现出光致变色性质，而配位化合物则在紫外区域和低能吸收带特征的配位化合物中激发后表现出光致变色性质，通过这种方式，可将光环化的激发波长从λ≦340 nm扩展到超过470 nm的波长。此外，还通过光致反应实现了化合物的发光性质的切换。
• US7755826B2
  申请人：——

  公开号：US7755826B2

  公开（公告）日：2010-07-13