7,7-Diphenyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene | 207742-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7,7-Diphenyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene
• 英文别名: 7,7-diphenyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 207742-47-0
• 化学式: C₂₀H₁₄S₂Si
• 分子量: 346.549
• InChiKey: GLBNWAANBUVBMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  四氰基乙烯 、 7,7-Diphenyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以85%的产率得到2-(7,7-Diphenyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)ethene-1,1,2-tricarbonitrile
  参考文献：
  名称：

  Preparation of 4,4-Diaryl-2-(tricyanoethenyl)dithienosiloles and Vapor-Chromic Behavior of the Film

  摘要：

  [GRAPHICS]Reactions of 4,4-diphenyl- and 4,4-di(p-tolyl)dithienosilole with tetracyanoethene (TCNE) in DMF gave coupling products 4,4-diphenyl- and 4,4-di(p-tolyl)-2-(tricycanoethenyl)dithienosilole (1a and 1b) in good yield. The films of 1b exhibited vapor-chromism, and the color of the film changed from red to blue-purple upon exposure to the vapor of organic solvents such as ethanol, methanol, acetonitrile, ethyl acetate, acetone, and hexane. The color reverted to the original red upon contact with chloroform vapor, indicating that this process is reversible.

  DOI：

  10.1021/ol025889y
• 作为产物：
  描述：

  3,3’-二溴-5,5’-双(三甲基硅基)-2,2’-联噻吩 在 正丁基锂 、 水 、 溴 作用下， 以 乙醚 为溶剂， 生成 7,7-Diphenyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene
  参考文献：
  名称：

  Synthesis and properties of dithienosiloles

  摘要：

  A series of dithienosilole derivatives were synthesized and some of their properties were investigated. UV spectra of dithienosiloles show absorption bands around 350 nm and their cyclic voltammograms display oxidation peaks at about 1.2 V vs. SCE. Nickel-catalyzed coupling of 2,6-dibromodithienosilole with the diGrignard reagent prepared from bis(5-bromothienyl)tetraethyldisilane afforded an alternating polymer composed of a 2,6-dithienyldithienosilole system and tetraethyldisilanylene unit. When the polymer film was doped with FeCl3 vapor, the film became conducting with the maximum conductivity of 7.0 x 10(-3) S/cm. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00643-8

文献信息

• Silole-spaced triarylamine derivatives as highly efficient organic sensitizers in dye-sensitized solar cells (DSSCs)
  作者：Sangwon Ko、Hyunbong Choi、Moon-Sung Kang、Hyonseok Hwang、Heesun Ji、Jinho Kim、Jaejung Ko、Youngjin Kang

  DOI：10.1039/b926163j

  日期：——

  Three new organic dyes that contain the dithienosilole (DTS) moiety as spacer have been synthesized and their photophysical/electrochemical properties, theoretical calculation and dye-sensitized solar cell (DSSC) performance have been investigated. The overall conversion efficiencies for DSSCs based on these dyes range from 6.73 to 7.50%, comparable to a (3–5′-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]2,2′-bithiophene-5-yl}-2-cyanoacrylic acid (JK-2)-sensitized device (7.63%), fabricated and measured under the same experimental conditions. The DSSC constructed from one of the three compounds shows a higher open-circuit voltage (VOC) compared to those of the other two dye sensitized solar cells due to an increased electron lifetime (τe) in the conduction band of TiO2.

  三种新的有机染料含有二噻吩硅氧烷（DTS）作为间隔物，它们的光物理/电化学性质、理论计算和染料敏化太阳能电池（DSSC）的性能已经过研究。基于这些染料的DSSC的总转换效率为6.73%至7.50%，与在相同实验条件下制造和测量的（3-5′-[N,N-双（9,9-二甲基芴-2-基）苯基]2,2′-联噻吩-5-基}-2-氰基丙烯酸（JK-2）敏化装置（7.63%）相当。由三种化合物之一构建的DSSC显示出更高的开路电压（VOC），这归因于TiO2传导带中电子寿命（τe）的增加。
• WO2008/109701
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and properties of dithienosiloles
  作者：Joji Ohshita、Mitsunori Nodono、Tsuguo Watanabe、Yoshiatsu Ueno、Atsutaka Kunai、Yutaka Harima、Kazuo Yamashita、Mitsuo Ishikawa

  DOI：10.1016/s0022-328x(97)00643-8

  日期：1998.2

  A series of dithienosilole derivatives were synthesized and some of their properties were investigated. UV spectra of dithienosiloles show absorption bands around 350 nm and their cyclic voltammograms display oxidation peaks at about 1.2 V vs. SCE. Nickel-catalyzed coupling of 2,6-dibromodithienosilole with the diGrignard reagent prepared from bis(5-bromothienyl)tetraethyldisilane afforded an alternating polymer composed of a 2,6-dithienyldithienosilole system and tetraethyldisilanylene unit. When the polymer film was doped with FeCl3 vapor, the film became conducting with the maximum conductivity of 7.0 x 10(-3) S/cm. (C) 1998 Elsevier Science S.A.
• Preparation of 4,4-Diaryl-2-(tricyanoethenyl)dithienosiloles and Vapor-Chromic Behavior of the Film
  作者：Joji Ohshita、Kwang-Hoi Lee、Mimi Hashimoto、Yoshihito Kunugi、Yutaka Harima、Kazuo Yamashita、Atsutaka Kunai

  DOI：10.1021/ol025889y

  日期：2002.5.1

  [GRAPHICS]Reactions of 4,4-diphenyl- and 4,4-di(p-tolyl)dithienosilole with tetracyanoethene (TCNE) in DMF gave coupling products 4,4-diphenyl- and 4,4-di(p-tolyl)-2-(tricycanoethenyl)dithienosilole (1a and 1b) in good yield. The films of 1b exhibited vapor-chromism, and the color of the film changed from red to blue-purple upon exposure to the vapor of organic solvents such as ethanol, methanol, acetonitrile, ethyl acetate, acetone, and hexane. The color reverted to the original red upon contact with chloroform vapor, indicating that this process is reversible.