1,1'-(5-(tert-butyl)-1,3-phenylene)bis(4-(3-(tert-butyl)-5-iodophenyl)-1H-1,2,3-triazole) | 1029002-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1'-(5-(tert-butyl)-1,3-phenylene)bis(4-(3-(tert-butyl)-5-iodophenyl)-1H-1,2,3-triazole)
• CAS: 1029002-27-4
• 化学式: C₃₄H₃₈I₂N₆
• 分子量: 784.525
• InChiKey: NJZSQSPKZSDQJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1'-(5-(tert-butyl)-1,3-phenylene)bis(4-(3-(tert-butyl)-5-iodophenyl)-1H-1,2,3-triazole) 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1,1'-(5-(tert-butyl)-1,3-phenylene)bis(4-(3-(tert-butyl)-5-((trimethylsilyl)ethynyl)phenyl)-1H-1,2,3-triazole)
  参考文献：
  名称：

  Strong, Size-Selective, and Electronically Tunable C−H···Halide Binding with Steric Control over Aggregation from Synthetically Modular, Shape-Persistent [3₄]Triazolophanes

  摘要：

  A series of shape-persistent [3(4)]triazolophanes bearing t-butyl or triethylene glycol (OTg) substituents on the phenylene linkers have been prepared in a modular manner from simple building blocks. Triazolophane-halide binding affinities were determined using UV titrations in order to help in understanding the driving forces behind the large receptor-anion binding strengths supported solely by CH hydrogen-bond donors. The fixed size of the central cavity provides a means for selective recognition of Cl- and Br- anions with large binding strengths (K-a > 1 000 000 M-1; Delta G > -8.5 kcal mol(-1)). The smaller F- and larger I- anions are bound less tightly by similar to 1 and similar to 3 orders of magnitude, respectively. The four triazole-based H-bond donors are believed to be of primary importance, while the four phenylene CH H-bond donors take on a secondary role. Consistent with this idea, the binding affinity can be tuned by as much as 1 kcal mol-1 by changing the character of the four phenylene-based substituents from more (OTg) to less (t-butyl) electron-donating. Preorganization was also found to play a central role, on the basis of comparisons with a foldamer analogue that shows much-reduced binding. Aggregation was facilitated as the substituents were changed from t-butyl to OTg, increasing the degree of self-association from K-E approximate to 0 to 230 M-1 in CD2Cl2. Diffusion NMR experiments established aggregation as opposed to dimerization. These findings indicate the importance of the cavity size for selective anion recognition as well as the role of the phenylene linkers in tuning the binding strengths and modulating the aggregation of the [3(4)]triazolophanes.

  DOI：

  10.1021/ja803341y
• 作为产物：
  描述：

  3,5-diazido-1-(tert-butyl)benzene 、 3-iodo-5-ethynyl-1-tert-butylbenzene 在 copper(II) sulfate 、 Erythorbic acid 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以91%的产率得到1,1'-(5-(tert-butyl)-1,3-phenylene)bis(4-(3-(tert-butyl)-5-iodophenyl)-1H-1,2,3-triazole)
  参考文献：
  名称：

  Strong, Size-Selective, and Electronically Tunable C−H···Halide Binding with Steric Control over Aggregation from Synthetically Modular, Shape-Persistent [3₄]Triazolophanes

  摘要：

  A series of shape-persistent [3(4)]triazolophanes bearing t-butyl or triethylene glycol (OTg) substituents on the phenylene linkers have been prepared in a modular manner from simple building blocks. Triazolophane-halide binding affinities were determined using UV titrations in order to help in understanding the driving forces behind the large receptor-anion binding strengths supported solely by CH hydrogen-bond donors. The fixed size of the central cavity provides a means for selective recognition of Cl- and Br- anions with large binding strengths (K-a > 1 000 000 M-1; Delta G > -8.5 kcal mol(-1)). The smaller F- and larger I- anions are bound less tightly by similar to 1 and similar to 3 orders of magnitude, respectively. The four triazole-based H-bond donors are believed to be of primary importance, while the four phenylene CH H-bond donors take on a secondary role. Consistent with this idea, the binding affinity can be tuned by as much as 1 kcal mol-1 by changing the character of the four phenylene-based substituents from more (OTg) to less (t-butyl) electron-donating. Preorganization was also found to play a central role, on the basis of comparisons with a foldamer analogue that shows much-reduced binding. Aggregation was facilitated as the substituents were changed from t-butyl to OTg, increasing the degree of self-association from K-E approximate to 0 to 230 M-1 in CD2Cl2. Diffusion NMR experiments established aggregation as opposed to dimerization. These findings indicate the importance of the cavity size for selective anion recognition as well as the role of the phenylene linkers in tuning the binding strengths and modulating the aggregation of the [3(4)]triazolophanes.

  DOI：

  10.1021/ja803341y

文献信息

• Pure CH Hydrogen Bonding to Chloride Ions: A Preorganized and Rigid Macrocyclic Receptor
  作者：Yongjun Li、Amar H. Flood

  DOI：10.1002/anie.200704717

  日期：2008.3.25