11,11'-((7,8,12,13,17,18-hexakis(methylthio)-5,10,15,20-tetraazaporphyrin-2,3-diyl)bis(sulfanediyl))bis(undecan-1-ol) | 1195989-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 11,11'-((7,8,12,13,17,18-hexakis(methylthio)-5,10,15,20-tetraazaporphyrin-2,3-diyl)bis(sulfanediyl))bis(undecan-1-ol)
• CAS: 1195989-39-9
• 化学式: C₄₄H₆₆N₈O₂S₈
• 分子量: 995.588
• InChiKey: QNAHWGADIPRGIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.63
• 重原子数：
  62.0
• 可旋转键数：
  30.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  149.38
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  11,11'-((7,8,12,13,17,18-hexakis(methylthio)-5,10,15,20-tetraazaporphyrin-2,3-diyl)bis(sulfanediyl))bis(undecan-1-ol) 、 zinc(II) chloride 以 四氢呋喃 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  Varying the Electrochemical Potential and Thickness of Porphyrazine SAMs by Molecular Design

  摘要：

  A series of multithiol-functionalized free-base and Zn-coordinated porphyrazines (pz's) have been prepared and characterized as self-assembled monolayers (SAMs) on Au. The synthetic flexibility of the pz's provides a unique opportunity to tune their electronic and chemical characteristics and to control the distance of the redox-active pz macrocycle from the Au surface. This allows us to study the reduction potentials of these surface-bound pz's as a function of film thickness and molecular charge distribution using angle-resolved X-ray photoelectron spectroscopy and cyclic voltammetry. Upon SAM formation, the reduction potentials of all pz's show a significant positive shift from their formal potentials when free in solution (up to similar to +1 V), with the magnitude of the shift inversely related to the Au-pz distance as determined from the film thickness of the pz SAM (thicknesses ranging from 3.5 to 11.8 angstrom). When the pz lies down oil the surface, in a SAM of thickness -3.5 angstrom, the charge distribution within a pz macrocycle also plays a role in determining the potential shift. These observations are consistent with our originally proposed mechanism for potential shifts upon binding to a metal surface based on image charge effects and with the analysis of Liu and Newton (J. Phys. Chem. 1994, 98, 7162).

  DOI：

  10.1021/jp905762p