2,12-dibromo-7-(3,5-di-tert-butyl-phenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,12-dibromo-7-(3,5-di-tert-butyl-phenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine
• 英文别名: 2,12-dibromo-7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydrodibenz[c,h]acridine；2,12-dibromo-DTDA；6,20-Dibromo-13-(3,5-ditert-butylphenyl)-2-azapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),5,7,13,17(22),18,20-nonaene；6,20-dibromo-13-(3,5-ditert-butylphenyl)-2-azapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),5,7,13,17(22),18,20-nonaene
• 化学式: C₃₅H₃₅Br₂N
• 分子量: 629.478
• InChiKey: YQCDUXMCTRXJGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,12-dibromo-7-(3,5-di-tert-butyl-phenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine 在 copper(l) iodide 、 四(三苯基膦)钯 sodium hydroxide 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 96.0h， 生成 2,12-bis[3-(4,4-dimethyloxazolin-2-yl)-4-hydroxyphenylethynyl]-[7-(3,5-di-tert-butylphenyl)dibenzo[c,h]acridine]
  参考文献：
  名称：

  Self-assembly of rectangles via building units bearing salen and oxazoline ligands

  摘要：

  Rigid spacer-chelator with the framework of 3 has been prepared. Building units with two parallel coordination sites such as salen and oxazoline units have also been synthesized. The spacer-chelators, 11 and 15, readily self-assembled with metal complexes such as Zn++ and Co++ to form molecular rectangles. The overall dimensions of the rectangles, 13 and 17, are 6.2 angstrom x 23.5 angstrom. The characterization of the supramolecules by NMR, mass spectroscopy, and X-ray crystal structures is also reported. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.09.063

文献信息

• Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent
  作者：Toshinobu Korenaga、Yusuke Kawauchi、Takahiro Kosaki、Tadashi Ema、Takashi Sakai

  DOI：10.1246/bcsj.78.2175

  日期：2005.12

  A molecular tweezer having two bidentate pentafluorophenyl (C6F5) groups was synthesized, and the π–π stacking ability of the C6F5 groups toward benzene derivatives in a polar organic solvent was evaluated. The structure of the molecular tweezer was revealed to be dimeric in the crystalline state by X-ray analysis. Association constants (Ka) between the molecular tweezer and aromatic guests in THF were found to be roughly correlated with the quadrupole moment (Qzz) of the guests, suggesting that the quadrupole–quadrupole contribution plays a significant role in the π–π interaction even in a polar organic solvent.

  合成了一种具有两个双叉五氟苯基（C6F5）基团的分子镊子，并评估了极性有机溶剂中 C6F5 基团对苯衍生物的 π-π 堆积能力。通过 X 射线分析，发现分子镊子在结晶状态下是二聚体结构。研究发现，分子镊子与芳香族客体在 THF 中的关联常数 (Ka) 与客体的四极矩 (Qzz) 大致相关，这表明即使在极性有机溶剂中，四极-四极贡献在 π-π 相互作用中也起着重要作用。
• Self-Assembly of Rectangles and Prisms via a Molecular “Clip”
  作者：Duckhyun Kim、Jong Hyub Paek、Moo-Jin Jun、Jin Yong Lee、Sang Ook Kang、Jaejung Ko

  DOI：10.1021/ic0508369

  日期：2005.10.1

  Aromatic molecular "clips" bearing two symmetrically bound platinum moieties have been prepared. The molecular "clip" 4 readily self-assembled with linear linkers such as 4,4'-bipyridyl, 1,4-bis[2-(4-isocyano-3,5-diisopropylphenyl)ethynyl]benzene, and nicotinic acid to form molecular rectangles. The overall dimensions of the rectangle 7 were 7.3 angstrom x 15.3 angstrom. The molecular "clip" also self-assembled with tritopic pyridyl and isocyanide ligands to form trigonal prismatic frameworks. The characterization of the supramolecules by multinuclear NMR, electrospray mass spectrometry, and X-ray crystal structures is also reported.
• Self-assembly of rectangles via building units bearing salen and oxazoline ligands
  作者：Duckhyun Kim、Il Jung、Kyu Ho Song、Sang Ook Kang、Jaejung Ko

  DOI：10.1016/j.jorganchem.2006.09.063

  日期：2006.12

  Rigid spacer-chelator with the framework of 3 has been prepared. Building units with two parallel coordination sites such as salen and oxazoline units have also been synthesized. The spacer-chelators, 11 and 15, readily self-assembled with metal complexes such as Zn++ and Co++ to form molecular rectangles. The overall dimensions of the rectangles, 13 and 17, are 6.2 angstrom x 23.5 angstrom. The characterization of the supramolecules by NMR, mass spectroscopy, and X-ray crystal structures is also reported. (c) 2006 Elsevier B.V. All rights reserved.