2,9-bis-4-(bromomethylphenyl)-1,10-phenanthroline | 136003-83-3

• 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: 2,9-bis-4-(bromomethylphenyl)-1,10-phenanthroline
• 英文别名: 2,9-Bis[4-(bromomethyl)phenyl]-1,10-phenanthroline
• CAS: 136003-83-3
• 化学式: C₂₆H₁₈Br₂N₂
• 分子量: 518.25
• InChiKey: AFHHYQHEKQKILZ-UHFFFAOYSA-N

物化性质

• 沸点：
  656.0±55.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-联吡啶 、 2,9-bis-4-(bromomethylphenyl)-1,10-phenanthroline 在 六氟磷酸钾 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以40%的产率得到
  参考文献：
  名称：

  A Switchable Hybrid [2]-Catenane Based on Transition Metal Complexation and π-Electron Donor−Acceptor Interactions

  摘要：

  A bimodal [2]-catenane has been synthesized via a copper(I) templated synthesis. The compound contains both a transition metal coordination site and a set of pi-electron rich and pi-electron deficient aromatic units suitable for the formation of acceptor-donor complexes. Each constituent ring is thus different from the other, and the organic backbone can adopt two favored contrasting orientations by circumrotation of one ring within the other: (i) in the metal complex mode, each dpp unit (dpp = 2,9-diphenyl-1,10-phenanthroline) is entwined about the other, while a cationic species is complexed in the coordination site thus created; (ii) in the organic pi-electron acceptor-donor complex mode, the dpp fragments are remote from one another, and the pi-electron rich and pi-electron deficient units stack to form a complex. The conversion of one binding mode to the other implies complete topographical rearrangement of the molecule. It can be triggered by adding or removing the cation center (Cu+, Li+, or H+), bonded to the dpp-containing complexing site. Interestingly, this switching process can be easily monitored by H-1 NMR, since it involves drastic relative orientational changes. It can also be evidenced by electronic spectroscopy. In particular, the proton-driven rearrangement reactions lead to significant changes in the absorption spectrum, which correspond to the appearance (by deprotonation) and disappearance (by protonation of the dpp) of a charge transfer band (around 470 nm) resulting from the pi-electron donor-acceptor noncovalent interaction.

  DOI：

  10.1021/ja954329+
• 作为产物：
  描述：

  甲基苯锂 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 反应 1.08h， 生成 2,9-bis-4-(bromomethylphenyl)-1,10-phenanthroline
  参考文献：
  名称：

  含2,9-二苯基-1,10-菲咯啉间隔基的双卟啉的合成

  摘要：

  描述了以倾斜方式布置的双卟啉的合成。四吡咯环通过2,9-二苯基-1,10-菲咯啉间隔基连接。已经研究了两种途径：逐步过程和涉及双环化步骤的直接策略。用双游离基卟啉由2,9-二（对甲苯基）-1,10-菲咯啉合成，总收率约为1％，制备了不对称的锌（II）卟啉游离碱体系，并在激发态能量和电子转移的观点。

  DOI：

  10.1016/s0040-4020(01)87125-8

文献信息

• Synthesis of new copper(I)-complexed rotaxanes via click chemistry
  作者：Stéphanie Durot、Pierre Mobian、Jean-Paul Collin、Jean-Pierre Sauvage

  DOI：10.1016/j.tet.2008.05.078

  日期：2008.9

  The Cu(I)-catalyzed dipolar cycloaddition of azides and terminal alkynes ('click' chemistry) has been used as a mild and efficient stoppering reaction for the preparation of new copper(I)-complexed rotaxanes. (C) 2008 Elsevier Ltd. All rights reserved.
• A Switchable Hybrid [2]-Catenane Based on Transition Metal Complexation and π-Electron Donor−Acceptor Interactions
  作者：David B. Amabilino、Christiane O. Dietrich-Buchecker、Aude Livoreil、Lluïsa Pérez-García、Jean-Pierre Sauvage、J. Fraser Stoddart

  DOI：10.1021/ja954329+

  日期：1996.4.24

  A bimodal [2]-catenane has been synthesized via a copper(I) templated synthesis. The compound contains both a transition metal coordination site and a set of pi-electron rich and pi-electron deficient aromatic units suitable for the formation of acceptor-donor complexes. Each constituent ring is thus different from the other, and the organic backbone can adopt two favored contrasting orientations by circumrotation of one ring within the other: (i) in the metal complex mode, each dpp unit (dpp = 2,9-diphenyl-1,10-phenanthroline) is entwined about the other, while a cationic species is complexed in the coordination site thus created; (ii) in the organic pi-electron acceptor-donor complex mode, the dpp fragments are remote from one another, and the pi-electron rich and pi-electron deficient units stack to form a complex. The conversion of one binding mode to the other implies complete topographical rearrangement of the molecule. It can be triggered by adding or removing the cation center (Cu+, Li+, or H+), bonded to the dpp-containing complexing site. Interestingly, this switching process can be easily monitored by H-1 NMR, since it involves drastic relative orientational changes. It can also be evidenced by electronic spectroscopy. In particular, the proton-driven rearrangement reactions lead to significant changes in the absorption spectrum, which correspond to the appearance (by deprotonation) and disappearance (by protonation of the dpp) of a charge transfer band (around 470 nm) resulting from the pi-electron donor-acceptor noncovalent interaction.
• Synthesis of bis-porphyrins containing a 2,9-diphenyl-1,10-phenanthroline spacer
  作者：Sylvie Chabdon-Noblat、Jean-Pierre Sauvage

  DOI：10.1016/s0040-4020(01)87125-8

  日期：1991.1

  10-phenanthroline spacer. Two routes have been investigated: a stepwise procedure and a direct strategy involving a double cyclisation step. From the bis-free base porphyrin, synthesized with an overall yield of ∼1% from 2,9-di(p-tolyl)-1,10-phenanthroline, an unsymmetrical zinc (II) porphyrin free base system was prepared and isolated in view of excited state energy and electron transfer.

  描述了以倾斜方式布置的双卟啉的合成。四吡咯环通过2,9-二苯基-1,10-菲咯啉间隔基连接。已经研究了两种途径：逐步过程和涉及双环化步骤的直接策略。用双游离基卟啉由2,9-二（对甲苯基）-1,10-菲咯啉合成，总收率约为1％，制备了不对称的锌（II）卟啉游离碱体系，并在激发态能量和电子转移的观点。