1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)-ethynyl)benzene | 1428643-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)-ethynyl)benzene
• 英文别名: TETEB；2-[5-[2-[3,5-Bis[2-[5-(2-trimethylsilylethynyl)thiophen-2-yl]ethynyl]phenyl]ethynyl]thiophen-2-yl]ethynyl-trimethylsilane
• CAS: 1428643-51-9
• 化学式: C₃₉H₃₆S₃Si₃
• 分子量: 685.169
• InChiKey: UVCOUJNYYXVTFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.76
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.25h， 生成 1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)-ethynyl)benzene
  参考文献：
  名称：

  Novel planar and star-shaped molecules: Synthesis, electrochemical and photophysical properties

  摘要：

  Three novel planar and star-shaped molecules containing thiophene-functionalized group and acetylenic spacers, 4((5 ''-iodo-[2,2':5',2 ''-terthiophen]-5-yl)ethynyl)aniline (I3TEA), 4,4'-([2,2':5',2 ''-terthiophene]-5,5 ''-diylbis(ethyne-2,1-diyl))dianiline (3TDDA), 1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)-ethynyl)benzene (TETEB) were synthesized through Sonogashira coupling reaction. Their photophysical and electrochemical properties were explored by UV-vis, photoluminescence (PL) emission and DFT calculation. Three compounds possess unusual phenomena of PL, with the concentration of gradually decreased, the intensity of PL firstly increased and then decreased, this may be due to the aggregate-enhanced emission (AEE) effect and aggregation-caused quenching (ACQ) effect. Their spectroscopic data demonstrate that D-pi-A-pi-D structured organic dye 3TDDA based on NH2 as donor units and 3T as acceptor units with acetylenic spacers it-conjugated chain between them exhibits good luminescent properties. Dye I3TEA with donor(D) acceptor(A) structure shows good charge transfer because of amino functional group and iodine atom. Octupolar organic pi-conjugated star-shaped molecule TETEB possesses excellent luminescent properties because of its unique structure applied in the optoelectronic field. The redox curves and results of DFT calculations suggest that three compounds have low ionization potential and low E-oxd. All the good properties demonstrate three compounds could be promising candidates for photovoltaic materials. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.01.047