diazidophenanthroline | 1173194-17-6

• 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: diazidophenanthroline
• 英文别名: 2,9-Bis[4-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]phenyl]-1,10-phenanthroline
• CAS: 1173194-17-6
• 化学式: C₃₆H₃₈N₈O₆
• 分子量: 678.748
• InChiKey: JJQZUDQCZSRHIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  diazidophenanthroline 、 methyl 4,7,10,13,15,18,21,24-octaoxa-2(2,9)-phenanthrolina-1,3(1,4),14(1,3)-tribenzenacyclotetracosaphane-145-carboxylate 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  用于合成功能化[3]邻苯二甲酸酯的“点击”方法：走向更高的互锁结构

  摘要：

  “双击”已被锁定：铜（I）模板合成与“点击”化学结合已被直接用于制备功能化[3]邻苯二酚。这种方法学允许构建更高连锁的体系结构，包括聚合物和网络以及适用于研究长距离光致电子转移过程的电子供体-受体纳米材料。

  DOI：

  10.1002/chem.200900536
• 作为产物：
  描述：

  (((((((1,10-phenanthroline-2,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate) 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以93%的产率得到diazidophenanthroline
  参考文献：
  名称：

  Optimizing reaction conditions for synthesis of electron donor-[60]fullerene interlocked multiring systems

  摘要：

  通过基于 Cu(I)-template 合成和 "点击 "化学的简单一锅程序，开发出了制备一系列带有电子供体和电子受体（[60]富勒烯）亚基的轮烷和卡替烷的反应条件。

  DOI：

  10.1039/c0jm02154g

文献信息

• Introduction of useful peripheral functional groups on [2]catenanes by combining Cu(i) template synthesis with “click” chemistry
  作者：Jackson D. Megiatto, Jr.、David I. Schuster

  DOI：10.1039/b9nj00486f

  日期：——

  protocols based on Cu(I) template synthesis and “click” reactions for the synthesis of functionalized [2]catenanes are described. A straightforward procedure, involving high dilution conditions at high temperatures (70 °C), affords [2]catenanes bearing two identical peripheral groups in high yields. For the preparation of non-symmetrically functionalized [2]catenanes, a second milder and simpler protocol

  两种协议基于 铜（I）描述了模板合成和用于功能化[2]邻苯二酚合成的“点击”反应。一种简单的方法，涉及在高温下（70°C）的高稀释条件，可以高产率得到[2]带有两个相同外围基团的邻苯二酚。为了制备非对称功能化的[2]儿茶酚，开发了第二种更温和，更简单的方案，推广并扩展了该方法。将外围官能团引入到链烷结构中，开辟了使用[2]邻苯二酚作为构建更复杂结构的构建基的可能性。
• [2]Catenanes Decorated with Porphyrin and [60]Fullerene Groups: Design, Convergent Synthesis, and Photoinduced Processes
  作者：Jackson D. Megiatto、David I. Schuster、Silke Abwandner、Gustavo de Miguel、Dirk M. Guldi

  DOI：10.1021/ja910149f

  日期：2010.3.24

  A new class of [2]catenanes containing zinc(II)-porphyrin (ZnP) and/or [60]fullerene (C-60) as appended groups has been prepared. A complete description of the convergent synthetic approach based on Cu(I) template methodology and "click" 1,3-dipolar cycloaddition chemistry is described. This new electron donor-acceptor catenane family has been subjected to extensive spectroscopic, computational, electrochemical and photophysical studies. H-1 NMR spectroscopy and computational analysis have revealed that the ZnP-C-60-[2]catenane adopts an extended conformation with the chromophores as far as possible from each other. A detailed photophysical investigation has revealed that upon irradiation the ZnP singlet excited state initially transfers energy to the (phenanthroline)(2)-Cu(I) complex core, producing a metal-to-ligand charge transfer (MLCT) excited state, which in turn transfers an electron to the C-60 group, generating the ZnP-[Cu(phen)(2)](2+)-C-60(center dot-) charge-separated state. A further charge shift from the (Cu(phen)(2)](2+) complex to the ZnP subunit, competitive with decay to the ground state, leads to the isoenergetic long distance ZnP center dot+-[Cu(phen)(2)](+)-C-60(center dot-) charge-separated radical pair state, which slowly decays back to the ground state on the microsecond time scale. The slow rate of back-electron transfer indicates that in this interlocked system, as in previously studied covalently linked ZnP-C-60 hybrid materials, this process occurs in the Marcus-inverted region.
• Convergent Synthesis and Photoinduced Processes in Multi-Chromophoric Rotaxanes
  作者：Jackson D. Megiatto、Ke Li、David I. Schuster、Amit Palkar、M. Ángeles Herranz、Luis Echegoyen、Silke Abwandner、Gustavo de Miguel、Dirk M. Guldi

  DOI：10.1021/jp101154k

  日期：2010.11.18

  A series of [2]rotaxane materials, in which [60]fullerene is linked to a macrocycle and ferrocene (Fc) moieties are placed at the termini of a thread, both of which possess a central Cu(I)-1,10-phenanthroline [Cu(phen)(2)](+) complex, were synthesized by self-assembly using Sauvage metal template methodology Two types of threads were constructed one with terminal ester linkages and a second with terminal 1,2,3-triazole linkages derived from Cu(I)-catalyzed "click' 1,3-cycloaddition reactions Model compounds lacking the fullerene moiety were prepared in an analogous manner The ability of the interlocked Fc-[Cu(phen)(2)](+)-C-60 hybrids to undergo electron transfer upon photoexcitation in benzonitrile, dichloromethane, and ortho-dichlorobenzene was investigated by means of time-resolved fluorescence and transient absorption spectroscopy, using excitation wavelengths directed at the fullerene and [Cu(phen)(2)](+) subunits The energies of the electronic excited states and charge separated (CS) states that might be formed upon photoexcitation were determined from spectroscopic and electrochemical data These studies showed that MLCT excited states of the copper complex in the fullerenerotaxanes were quenched by electron transfer to the fullerene in benzonitrile, resulting in charge separated states with oxidized copper and reduced fullerene moieties, (Fc)(2)-[Cu(phen)(2)](2+)-C-60 (-) Even though electron transfer from Fe to the oxidized copper complex is predicted to be exergonic by 0 16 to 0 20 eV, no unequivocal evidence in support of such a process was obtained The conclusion that Fe plays no role in the photoinduced processes in our systems rests on the lack of enhancement of the lifetime of the charge separated state, as measured by decay of C-60 (-) at similar to 1000 nm, since one-electron oxidized Fe is very difficult to detect spectroscopically in the 500-800 nm spectral region