pentiptycene diacetylene | 214461-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: pentiptycene diacetylene
• 英文别名: 3,14-Diethynylnonacyclo[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
• CAS: 214461-10-6
• 化学式: C₃₈H₂₂
• 分子量: 478.593
• InChiKey: OUKNYUXLDRCLOU-UHFFFAOYSA-N

物化性质

• 熔点：
  437 °C
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  Agn-PC-0LP5SU 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到pentiptycene diacetylene
  参考文献：
  名称：

  Direct detection of ultralow trace amounts of isocyanates in air using a fluorescent conjugated polymer

  摘要：

  通过含有戊环戊烯和四苯乙烯单元的共轭聚合物，通过荧光熄灭方法在 ppb 水平上直接检测空气中的脂肪族和芳香族异氰酸酯。

  DOI：

  10.1039/c3cc47934j

文献信息

• Synthesis, Rotational Dynamics, and Photophysical Characterization of a Crystalline Linearly Conjugated Phenyleneethynylene Molecular Dirotor
  作者：Melissa Hughs、Miguel Jimenez、Saeed Khan、Miguel A. Garcia-Garibay

  DOI：10.1021/jo4004053

  日期：2013.6.7

  which the two flanking ethynylphenylene rotators can explore various torsion angles; this allows the BEPEB fluorophore dynamics to persist in the solid state. X-ray diffraction studies have shown that molecular dirotor 1 is packed so that all the BEPEB fluorophores adopt a parallel alignment, this is ideal for the development of functional materials. Variable temperature, quadrupolar echo 2H NMR studies

  我们报告6,13-​​双（（4-（3-（3-（3-甲氧基苯基）-3,3-二苯基丙-1-yn-1-yl）苯基）的合成，晶体结构，固态动力学和光物理性质乙炔基）-5,7,12,14-四氢-5,14：7,12-双（[1,2，benzeno）并五苯（1），具有1,4-双（（4-乙炔基苯基）乙炔基苯（BEPEB）发色团。戊二烯结合到分子转子中提供了一个中心定子和一个固定的亚苯基环，两个侧键的乙炔基亚苯基转子可相对于它们探索不同的扭转角。这样可以使BEPEB荧光团动力学保持固态。X射线衍射研究表明分子转子1包装好使所有BEPEB荧光团都采用平行排列，这对于功能材料的开发是理想的。可变温度，四极回波21 H NMR研究表明，亚苯基旋转翻转具有9.0kcal / mol的活化能和约2.6MHz的室温翻转频率。最后，通过在溶液，玻璃和晶体中的测量，我们获得了证据，亚苯基亚乙炔发色团的荧光激发和发射光谱取决于
• Fluorous Biphase Synthesis of a Poly(p-phenyleneethynylene) and its Fluorescent Aqueous Fluorous-Phase Emulsion
  作者：Jeewoo Lim、Timothy M. Swager

  DOI：10.1002/anie.201003111

  日期：——

  highly fluorinated compound with a rigid three‐dimensional architecture was synthesized as a monomer for poly(p‐phenyleneethynylene)s (PPEs). Fluorous biphase reactions were applied for the synthesis of a PPE that is soluble only in fluorous solvents. A fluorous solution of the polymer could be processed into aqueous emulsions that display high fluorescence quantum yields (see picture).

  这只是一个阶段：合成了具有刚性三维结构的高度氟化的化合物，作为聚对苯撑乙炔撑（PPE）的单体。荧光双相反应用于合成仅可溶于氟溶剂的PPE。可以将聚合物的氟溶液加工成具有高荧光量子产率的水性乳液（参见图片）。
• Detection of Ethylene Gas by Fluorescence Turn-On of a Conjugated Polymer
  作者：Birgit Esser、Timothy M. Swager

  DOI：10.1002/anie.201003899

  日期：2010.11.15

  Ripe fruits: The fluorescence of a conjugated polymer is quenched by the presence of copper(I) moieties. Upon exposure to ethylene gas the copper complexes bind to ethylene and no longer quench the polymer fluorescence (see picture). This sensory concept can be used in solution and in thin films.

  成熟的水果：共轭聚合物的荧光因铜（I）部分的存在而猝灭。暴露于乙烯气体后，铜络合物与乙烯结合，不再猝灭聚合物荧光（参见图片）。该感官概念可用于溶液和薄膜中。
• Platinum Acetylide Complexes Containing Iptycene as Cores: A New Family of Unexpected Efficient Organometallic Gelators
  作者：Jing Zhang、Xing-Dong Xu、Li-Jun Chen、Qi Luo、Nai-Wei Wu、De-Xian Wang、Xiao-Li Zhao、Hai-Bo Yang

  DOI：10.1021/om2002987

  日期：2011.8.8

  and 13C) and mass spectroscopy and elemental analysis. Unexpectedly, all compounds presented good gel formation properties in some common organic solvents. The morphology of the xerogels was investigated by scanning electron microscopy (SEM). An investigation using electronic absorption and emission spectra was carried out to study the spectroscopic properties of all organometallic complexes in both

  已成功合成了新的含乙炔并以3,4,5-三（烷氧基）苯基取代基封端的茂金属构建基的乙炔铂衍生物新家族。新设计的配合物的结构通过多核NMR（1 H，31 P和13 C）以及质谱和元素分析进行表征。出乎意料的是，所有化合物在某些常见的有机溶剂中均表现出良好的凝胶形成性能。通过扫描电子显微镜（SEM）研究干凝胶的形态。进行了使用电子吸收和发射光谱的研究，以研究溶液和凝胶状态下所有有机金属配合物的光谱性质。
• 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.