2,3-bis(2,5-dimethylthiophen-3-yl)-1,1-dimethyl-1H-benzo[b]silolo[2,3-d]-thiophene

• 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: 2,3-bis(2,5-dimethylthiophen-3-yl)-1,1-dimethyl-1H-benzo[b]silolo[2,3-d]-thiophene
• 英文别名: 2,3-Bis(2,5-dimethylthiophen-3-yl)-1,1-dimethylsilolo[3,2-b][1]benzothiole；2,3-bis(2,5-dimethylthiophen-3-yl)-1,1-dimethylsilolo[3,2-b][1]benzothiole
• 化学式: C₂₄H₂₄S₃Si
• 分子量: 436.738
• InChiKey: IZQDEXLBQBWUHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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(2,5-dimethylthiophen-3-yl)-1,1-dimethyl-1H-benzo[b]silolo[2,3-d]-thiophene 以 苯 为溶剂， 生成
  参考文献：
  名称：

  A Highly Efficient Silole-Containing Dithienylethene with Excellent Thermal Stability and Fatigue Resistance: A Promising Candidate for Optical Memory Storage Materials

  摘要：

  Diarylethene compounds are potential candidates for applications in optical memory storage systems and photoswitchable molecular devices; however, they usually show low photocycloreversion quantum yields, which result in ineffective erasure processes. Here, we present the first highly efficient photochromic silole-containing dithienylethene with excellent thermal stability and fatigue resistance. The photochemical quantum yields for photocyclization and photocycloreversion of the compound are found to be high and comparable to each other; the latter of which is rarely found in diarylethene compounds. These would give rise to highly efficient photoswitchable material with effective writing and erasure processes. Incorporation of the silole moiety as a photochromic dithienylethene backbone also was demonstrated to enhance the thermal stability of the closed form, in which the thermal backward reaction to the open form was found to be negligible even at 100 °C, which leads to a promising candidate for use as photoswitchable materials and optical memory storage.

  DOI：

  10.1021/ja5101855
• 作为产物：
  描述：

  3-碘-2,5-二甲基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 bis(η3-allyl-μ-chloropalladium(II)) 、 三叔丁基膦 、 potassium carbonate 、 二异丙胺 、 三苯基膦 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 2,3-bis(2,5-dimethylthiophen-3-yl)-1,1-dimethyl-1H-benzo[b]silolo[2,3-d]-thiophene
  参考文献：
  名称：

  [EN] ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF
  [FR] COMPOSÉS PHOTOCHROMIQUES ROBUSTES COMPORTANT UN CYCLE HÉTÉROCYCLIQUE CONTENANT DU PHOSPHORE OU DU SILICIUM ET LEURS PROCÉDÉS DE PRODUCTION

  摘要：

  在一个实施方案中，提供了一种新型的含有二芳基乙烯的光致变色化合物，该化合物将含有硅或磷的杂环引入到二芳基乙烯主链的“乙烯”部分，已经显示出能够展现出可调节、稳健且热稳定的光致变色性能。同时，还提供了合成这些化合物的方法，以及这些化合物的用途，因为它们可以用作光记录材料和其他光功能设备中的光致变色层。

  公开号：

  WO2015188790A1

文献信息

• [EN] ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF<br/>[FR] COMPOSÉS PHOTOCHROMIQUES ROBUSTES COMPORTANT UN CYCLE HÉTÉROCYCLIQUE CONTENANT DU PHOSPHORE OU DU SILICIUM ET LEURS PROCÉDÉS DE PRODUCTION
  申请人：UNIV HONG KONG

  公开号：WO2015188790A1

  公开（公告）日：2015-12-17

  In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon-or phosphorus-containing heterocycles into the "ethene" part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.

  在一个实施方案中，提供了一种新型的含有二芳基乙烯的光致变色化合物，该化合物将含有硅或磷的杂环引入到二芳基乙烯主链的“乙烯”部分，已经显示出能够展现出可调节、稳健且热稳定的光致变色性能。同时，还提供了合成这些化合物的方法，以及这些化合物的用途，因为它们可以用作光记录材料和其他光功能设备中的光致变色层。
• A Highly Efficient Silole-Containing Dithienylethene with Excellent Thermal Stability and Fatigue Resistance: A Promising Candidate for Optical Memory Storage Materials
  作者：Jacky Chi-Hung Chan、Wai Han Lam、Vivian Wing-Wah Yam

  DOI：10.1021/ja5101855

  日期：2014.12.10

  Diarylethene compounds are potential candidates for applications in optical memory storage systems and photoswitchable molecular devices; however, they usually show low photocycloreversion quantum yields, which result in ineffective erasure processes. Here, we present the first highly efficient photochromic silole-containing dithienylethene with excellent thermal stability and fatigue resistance. The photochemical quantum yields for photocyclization and photocycloreversion of the compound are found to be high and comparable to each other; the latter of which is rarely found in diarylethene compounds. These would give rise to highly efficient photoswitchable material with effective writing and erasure processes. Incorporation of the silole moiety as a photochromic dithienylethene backbone also was demonstrated to enhance the thermal stability of the closed form, in which the thermal backward reaction to the open form was found to be negligible even at 100 °C, which leads to a promising candidate for use as photoswitchable materials and optical memory storage.