N^4,4'-bis(1-pyrenylmethyl)-[2,2-dipyridyl]-4,4'-dicarboxamide | 1497435-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N^4,4'-bis(1-pyrenylmethyl)-[2,2-dipyridyl]-4,4'-dicarboxamide
• 英文别名: N⁴,N^4'-bis(1-pyrenylmethyl)-[2,2'-bipyridyl]-4,4'-dicarboxamide；n4,n4'-bis(1-pyrenylmethyl)-[2,2'-bipyridyl]-；N-(pyren-1-ylmethyl)-2-[4-(pyren-1-ylmethylcarbamoyl)pyridin-2-yl]pyridine-4-carboxamide
• CAS: 1497435-23-0
• 化学式: C₄₆H₃₀N₄O₂
• 分子量: 670.77
• InChiKey: VVJSEFWPCABZRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  52.0
• 可旋转键数：
  7.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  83.98
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 N^4,4'-bis(1-pyrenylmethyl)-[2,2-dipyridyl]-4,4'-dicarboxamide 以 甲苯 为溶剂， 反应 24.0h， 生成 Re(N^4,4'-bis(1-pyrenylmethyl)-[2,2-dipyridyl]-4,4'-dicarboxamide)(CO)3Cl
  参考文献：
  名称：

  Noncovalent Immobilization of Electrocatalysts on Carbon Electrodes for Fuel Production

  摘要：

  We show that molecular catalysts for fuel-forming reactions can be immobilized on graphitic carbon electrode surfaces via noncovalent interactions. A pyrene-appended bipyridine ligand (P) serves as the linker between each complex and the surface. Immobilization of a rhodium proton-reduction catalyst, [Cp*Rh(P)Cl]Cl (1), and a rhenium CO2-reduction catalyst, Re(P)(CO)(3)Cl (2), afford electrocatalytically active assemblies. X-ray photoelectron spectroscopy and electrochemistry confirm catalyst immobilization. Reduction of 1 in the presence of p-toluenesulfonic acid results in catalytic H-2 production, while reduction of 2 in the presence of CO2 results in catalytic CO production.

  DOI：

  10.1021/ja4099609
• 作为产物：
  描述：

  2,2'-联吡啶-4,4'-二甲酸 在 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 N^4,4'-bis(1-pyrenylmethyl)-[2,2-dipyridyl]-4,4'-dicarboxamide
  参考文献：
  名称：

  Noncovalent Immobilization of Electrocatalysts on Carbon Electrodes for Fuel Production

  摘要：

  We show that molecular catalysts for fuel-forming reactions can be immobilized on graphitic carbon electrode surfaces via noncovalent interactions. A pyrene-appended bipyridine ligand (P) serves as the linker between each complex and the surface. Immobilization of a rhodium proton-reduction catalyst, [Cp*Rh(P)Cl]Cl (1), and a rhenium CO2-reduction catalyst, Re(P)(CO)(3)Cl (2), afford electrocatalytically active assemblies. X-ray photoelectron spectroscopy and electrochemistry confirm catalyst immobilization. Reduction of 1 in the presence of p-toluenesulfonic acid results in catalytic H-2 production, while reduction of 2 in the presence of CO2 results in catalytic CO production.

  DOI：

  10.1021/ja4099609

文献信息

• Strong Electronic Coupling of Molecular Sites to Graphitic Electrodes via Pyrazine Conjugation
  作者：Megan N. Jackson、Seokjoon Oh、Corey J. Kaminsky、Sterling B. Chu、Guanghui Zhang、Jeffrey T. Miller、Yogesh Surendranath

  DOI：10.1021/jacs.7b10723

  日期：2018.1.24

  Glassy carbon electrodes were functionalized with redox-active moieties by condensation of o-phenylenediamine :derivatives with o-quinone sites native to graphitic carbon surfaces. Electrochemical and spectroscopic investigations establish that these graphite-conjugated catalysts (GCcs) exhibit strong electronic coupling to the electrode, leading to electron transfer (ET) behavior that diverges fundamentally from that of solution-phase. or-Surface-tethered analogues. We find that (1) ET is not observed between the electrode and a redox-active GCC moiety regardless of applied potential. (2) ET is observed at GCCs only if the interfacial reaction is ion coupled. (3) Even when. ET is observed, the oxidation state of a transition metal GCC site remains unchanged. From these observations, we construct a mechanistic model for GCC sites in which ET behavior is identical to that of catalytically active metal surfaces rather than to that of molecules in solution. These results suggest that GCCs provide a versatile platform for bridging molecular and heterogeneous electrocatalysis.
• Noncovalent Immobilization of Electrocatalysts on Carbon Electrodes for Fuel Production
  作者：James D. Blakemore、Ayush Gupta、Jeffrey J. Warren、Bruce S. Brunschwig、Harry B. Gray

  DOI：10.1021/ja4099609

  日期：2013.12.11

  We show that molecular catalysts for fuel-forming reactions can be immobilized on graphitic carbon electrode surfaces via noncovalent interactions. A pyrene-appended bipyridine ligand (P) serves as the linker between each complex and the surface. Immobilization of a rhodium proton-reduction catalyst, [Cp*Rh(P)Cl]Cl (1), and a rhenium CO2-reduction catalyst, Re(P)(CO)(3)Cl (2), afford electrocatalytically active assemblies. X-ray photoelectron spectroscopy and electrochemistry confirm catalyst immobilization. Reduction of 1 in the presence of p-toluenesulfonic acid results in catalytic H-2 production, while reduction of 2 in the presence of CO2 results in catalytic CO production.