5,14[1',2']:7,12[1',2']-dibenzo-5,7,12,14-tetrahydro-6,13-bis(4'-octyloxyphenylethynyl)pentacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5,14[1',2']:7,12[1',2']-dibenzo-5,7,12,14-tetrahydro-6,13-bis(4'-octyloxyphenylethynyl)pentacene
• 英文别名: 3,14-Bis[2-(4-octoxyphenyl)ethynyl]nonacyclo[14.6.6.65,12.02,15.04,13.06,11.017,22.023,28.029,34]tetratriaconta-2(15),3,6,8,10,13,17,19,21,23,25,27,29,31,33-pentadecaene；3,14-bis[2-(4-octoxyphenyl)ethynyl]nonacyclo[14.6.6.65,12.02,15.04,13.06,11.017,22.023,28.029,34]tetratriaconta-2(15),3,6,8,10,13,17,19,21,23,25,27,29,31,33-pentadecaene
• 化学式: C₆₆H₆₂O₂
• 分子量: 887.217
• InChiKey: IQSXBEBHNKOQAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(n-octyloxy)-iodobenzene 、 pentiptycene diacetylene 在 四(三苯基膦)钯 二异丙胺 作用下， 以 苯 为溶剂， 以90%的产率得到5,14[1',2']:7,12[1',2']-dibenzo-5,7,12,14-tetrahydro-6,13-bis(4'-octyloxyphenylethynyl)pentacene
  参考文献：
  名称：

  Probing the Intrachain and Interchain Effects on the Fluorescence Behavior of Pentiptycene-Derived Oligo(p-phenyleneethynylene)s

  摘要：

  The synthesis, crystal structure, and fluorescence behavior of acetylene-bridged pentiptycene dimer (2), trimer (3), and tetramer (4) are reported. For comparison, a phenylene-pentiptycene-phenylene three-ring system (5) is also investigated. As a result of the unique intrachain pentiptycene-pentiptycene interactions in 3 and 4, their twisted conformers are populated in polar solvents and at low temperatures, and the phenomenon of nonequilibration of excited rotational conformers is observed. Twisting of the pi-conjugated backbones leads to blue-shifted absorption and fluorescence spectra and increased fluorescence quantum yields and lifetimes. The fluorescence spectra of 2-4 undergo small red shifts but large intensity variations in the 0-1 vs 0-0 bands on going from solutions to thin solid films, which can be accounted for by the reabsorption effect. However, the reduction in fluorescence quantum yields for 2-4 in films vs solutions is mainly attributed to efficient interchain exciton migration to nonfluorescent energy traps. In contrast, the behavior of nonequilibration of excited rotamers is not observed for 5 in solutions. Compound 5 forms J-type aggregates through terminal phenylene pi-stackings in the solid state, resulting in a new absorption band at 377 nm and large red shifts of the structured fluorescence spectra.

  DOI：

  10.1021/ja0640389

文献信息

• Using “Internal Free Volume” to Increase Chromophore Alignment
  作者：Timothy M. Long、Timothy M. Swager

  DOI：10.1021/ja017499x

  日期：2002.4.1

  Triptycenes have general applicability for increasing the alignment of fluorescent and dichroic dyes in LC hosts. Dyes containing varying numbers of triptycenes were synthesized to study the effect of free-volume alignment of triptycenes on the alignment of dyes. These dyes were designed such that multiple triptycenes could be incorporated and the triptycene-free volume is coincident to the aspect ratio of the dye, allowing a cooperative effect to increase their overall average alignment. With increasing triptycene incorporation, a stepwise increase in the alignment parameters of each dye was seen. It was also found that the attachment of one triptycene group has a negligible effect on the optical switching response times of the dyes. This can be a powerful tool for designing dyes with higher alignments for a variety of applications including guest-host reflective LCDs and holographic data storage.
• Probing the Intrachain and Interchain Effects on the Fluorescence Behavior of Pentiptycene-Derived Oligo(<i>p</i>-phenyleneethynylene)s
  作者：Jye-Shane Yang、Jyu-Lun Yan、Chung-Yu Hwang、Shih-Yi Chiou、Kang-Ling Liau、Hui-Hsu Gavin Tsai、Gene-Hsiang Lee、Shie-Ming Peng

  DOI：10.1021/ja0640389

  日期：2006.11.1

  The synthesis, crystal structure, and fluorescence behavior of acetylene-bridged pentiptycene dimer (2), trimer (3), and tetramer (4) are reported. For comparison, a phenylene-pentiptycene-phenylene three-ring system (5) is also investigated. As a result of the unique intrachain pentiptycene-pentiptycene interactions in 3 and 4, their twisted conformers are populated in polar solvents and at low temperatures, and the phenomenon of nonequilibration of excited rotational conformers is observed. Twisting of the pi-conjugated backbones leads to blue-shifted absorption and fluorescence spectra and increased fluorescence quantum yields and lifetimes. The fluorescence spectra of 2-4 undergo small red shifts but large intensity variations in the 0-1 vs 0-0 bands on going from solutions to thin solid films, which can be accounted for by the reabsorption effect. However, the reduction in fluorescence quantum yields for 2-4 in films vs solutions is mainly attributed to efficient interchain exciton migration to nonfluorescent energy traps. In contrast, the behavior of nonequilibration of excited rotamers is not observed for 5 in solutions. Compound 5 forms J-type aggregates through terminal phenylene pi-stackings in the solid state, resulting in a new absorption band at 377 nm and large red shifts of the structured fluorescence spectra.