1-ethynyl-2,3,4,5-tetraphenylbenzene | 217489-68-4

• 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: 1-ethynyl-2,3,4,5-tetraphenylbenzene
• CAS: 217489-68-4
• 化学式: C₃₂H₂₂
• 分子量: 406.527
• InChiKey: VJOYEHMWLBDRFP-UHFFFAOYSA-N

物化性质

• 沸点：
  498.0±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3,3'-(1,4-phenylene)bis(2,4,5-triphenylcyclopenta-2,4-dien-1-one) 、 1-ethynyl-2,3,4,5-tetraphenylbenzene 在 三氯化铁 作用下， 以 二苯醚 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 35.0h， 以37 mg的产率得到Hentetracontacyclo[56.4.4.437,42.445,46.449,50.453,54.26,64.211,14.215,18.219,22.223,26.257,65.127,31.132,36.05,63.062,66.469,95.476,77.480,81.484,85.273,94.010,70.041,86.067,99.068,71.072,98.074,75.078,79.082,83.087,103.088,104.089,105.090,108.091,109.092,112.093,113.096,100.097,101.0102,114.0106,107.0110,111]tetradecahecta-a(69),1(62),1a(2a),2,3a(87),4,4a(5a),6(70),6a(84),7,7a(8a),9,9a(10a),11(96),11a(12a),12,13a(14a),14(95),15(94),16,18(93),19(92),20,22(91),23(90),24,26(89),27,29,31(88),32,34,36,38,40,42(83),43,45,47,49,51,53,55,57(68),58,60,63,65,67(99),71,73,75,77,79,81,85,97-heptapentacontaene
  参考文献：
  名称：

  From Branched Polyphenylenes to Graphite Ribbons

  摘要：

  This article presents the synthesis of graphitic nanoribbons (similar to1 nm wide), containing extended conjugated all-benzenoid segments. These were obtained by intramolecular oxidative cyclode-hydrogenation of soluble branched polyphenylenes 6, which were prepared by repetitive Diels-Alder cycloaddition of 1,4-bis(2,4,5-triphenylcyclopentadienone-3-yl)benzene (1) and diethynylterphenyl (5) in good yield. While insolubility of the obtained graphite ribbons 7 precluded standard spectroscopic structure elucidation, the electronic and vibrational properties were probed by solid-state UV-vis, Raman, and infrared spectroscopy. A wide and unstructured absorption band covering the visible range of the electronic spectrum (lambda(max) similar to 800 nm) is observed, confirming the highly extended conjugated framework. The structure proof of the ribbon-type polymer is supported by the inclusion of appropriate model compounds. The profile of the visible Raman spectrum of the material is similar to that of a discrete polycyclic aromatic hydrocarbon (PAH) C(222)H(42), characterized by two strong bands (at 1603 and 1322 cm(-1)), corresponding to the G and D bands of graphite. The obtained graphite ribbons are not linear but rather contain "kinks" due to the structural design of the polyphenylene precursor. High-resolution transmission electron microscopy (HRTEM) images of the graphite ribbons 7 disclose two different domains: one is an ordered graphite layer structure with a layer distance of ca. 3.8 Angstrom, and one is disordered due to the existence of "kinks" in the obtained polymers and/or random stacking of graphite ribbons. Attempts to make linear analogues are so far unsuccessful, emphasizing the critical importance of the geometry of the polyphenylene scaffold to successful oxidative cyclodehydrogenation.

  DOI：

  10.1021/ma0257752
• 作为产物：
  描述：

  四苯基环戊二烯酮 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二苯醚 为溶剂， 生成 1-ethynyl-2,3,4,5-tetraphenylbenzene
  参考文献：
  名称：

  A Soluble C60 Graphite Segment

  摘要：

  At the limits of analytical investigation one finds the nanodimensional C60 graphite segment 1, which, thanks to its long-chain alkyl substituents, is soluble. Monolayers of 1 on graphite can be characterized by scanning tunneling microscopy.

  DOI：

  10.1002/(sici)1521-3773(19981016)37:19<2696::aid-anie2696>3.0.co;2-e