| 827039-30-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• CAS: 827039-30-5
• 化学式: C₃₀H₃₄N₈O₄S₈
• 分子量: 827.179
• InChiKey: KEPUENHKTKICMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  50.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  183.52
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[2-[(4-methylphenyl)disulfanyl]ethyl]-4-[[5-[4-[2-[(4-methylphenyl)disulfanyl]ethylamino]-4-oxobutyl]sulfanyl-9,10,14,15,19,20-hexakis(methylsulfanyl)-2,7,12,17,21,22,23,24-octazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1(20),2,4,6(24),7,9,11(23),12,14,16,18-undecaen-4-yl]sulfanyl]butanamide
  参考文献：
  名称：

  Surface-Bound Porphyrazines:  Controlling Reduction Potentials of Self-Assembled Monolayers through Molecular Proximity/Orientation to a Metal Surface

  摘要：

  We report the preparation of two novel H-2[pz(A(n);B4-n)] porphyrazines (pzs) which were designed to position themselves quite differently when attached to a surface: one to form a standard self-assembled monolayer (SAM) roughly perpendicular to a surface, the other to lie horizontally along a surface. As the former, we synthesized a pz, 1, where one pyrrole group is functionalized with two thioethers terminated in mercaptides (SR, R = (CH2)(3)CONH(CH2)(2)S-), each protected as a disulfide, and -S-Me is attached to the other pyrrole sites; the latter is a pz, 2, with dialkoxybenzo groups fused to two trans-pyrroles of the pz ring, and SR groups are attached to the other pair of pyrroles. Nanostructures of 1 and 2 were successfully patterned on gold surfaces via dip-pen nanolithography, and the predicted molecular orientation of the resulting structures was confirmed by topographic AFM images. The two pzs exhibit similar reduction potentials in solution. Both show large shifts in potential upon surface binding, with the magnitude of the shift depending on the proximity/orientation of the pz to the surface. The first reduction potential of the "vertically" aligned 1 shifts by ca. +430 mV when incorporated in a binary pz/hexanethiol SAM, while that for 2, which lies flat, shifts by ca. +800 mV; the potential thus shifts by ca. +370 mV upon taking a given pz that stands atop a two-legged insulating "standoff" in a traditional SAM and "laying it down". We suggest these observed effects can be explained by image-charge energetics, and this is supported by a simple model.

  DOI：

  10.1021/ja045270m
• 作为产物：
  描述：

  dibutyl 4,4'-((7,8,12,13,17,18-hexakis(methylthio)-5,10,15,20-tetraazaporphyrin-2,3-diyl)bis(sulfanediyl))dibutyrate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以96.6%的产率得到
  参考文献：
  名称：

  Surface-Bound Porphyrazines:  Controlling Reduction Potentials of Self-Assembled Monolayers through Molecular Proximity/Orientation to a Metal Surface

  摘要：

  We report the preparation of two novel H-2[pz(A(n);B4-n)] porphyrazines (pzs) which were designed to position themselves quite differently when attached to a surface: one to form a standard self-assembled monolayer (SAM) roughly perpendicular to a surface, the other to lie horizontally along a surface. As the former, we synthesized a pz, 1, where one pyrrole group is functionalized with two thioethers terminated in mercaptides (SR, R = (CH2)(3)CONH(CH2)(2)S-), each protected as a disulfide, and -S-Me is attached to the other pyrrole sites; the latter is a pz, 2, with dialkoxybenzo groups fused to two trans-pyrroles of the pz ring, and SR groups are attached to the other pair of pyrroles. Nanostructures of 1 and 2 were successfully patterned on gold surfaces via dip-pen nanolithography, and the predicted molecular orientation of the resulting structures was confirmed by topographic AFM images. The two pzs exhibit similar reduction potentials in solution. Both show large shifts in potential upon surface binding, with the magnitude of the shift depending on the proximity/orientation of the pz to the surface. The first reduction potential of the "vertically" aligned 1 shifts by ca. +430 mV when incorporated in a binary pz/hexanethiol SAM, while that for 2, which lies flat, shifts by ca. +800 mV; the potential thus shifts by ca. +370 mV upon taking a given pz that stands atop a two-legged insulating "standoff" in a traditional SAM and "laying it down". We suggest these observed effects can be explained by image-charge energetics, and this is supported by a simple model.

  DOI：

  10.1021/ja045270m