4'-(8-mercaptooctyloxy)-2,2':6',2''-terpyridine | 785051-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4'-(8-mercaptooctyloxy)-2,2':6',2''-terpyridine
• 英文别名: 8-(2,2':6',2"-terpyridin-4'-yloxy)iodooctane-1-thiol；8-(2,2':6',2''-terpyridin-4'-yloxy)octane-1-thiol；8-[2,2a(2):6a(2),2a(2)a(2)-Terpyridin]-4a(2)-yl-1-octanethiol；8-(2,6-dipyridin-2-ylpyridin-4-yl)oxyoctane-1-thiol
• CAS: 785051-46-9
• 化学式: C₂₃H₂₇N₃OS
• 分子量: 393.553
• InChiKey: JFTOMRTYHHWEIV-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  556.4±50.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-(8-mercaptooctyloxy)-2,2':6',2''-terpyridine 、 ammonium hexafluorophosphate 、 dichlorotetrakis(dimethylsulfoxide)ruthenium(II) 以 乙醇 为溶剂， 以35%的产率得到[Ru(8-(2,2':6',2''-terpyridin-4'-yloxy)octane-1-thiol)2](PF6)2
  参考文献：
  名称：

  Molecular self-assembled monolayers of ruthenium(II)-terpyridine dithiol complex on gold electrode and nanoparticles

  摘要：

  We describe the formation of stable dithiol-bifunctionalized Ru(II)-terpyridine monolayer onto gold electrode. The coverage-dependent behavior onto gold electrode has been studied by electrochemical technique. The stability, surface charge coverage, and electrontransfer kinetics were assessed by cyclic voltammetry. Functionalized monolayer-protected Au clusters (MPCs) were also prepared. The spectroscopic characterization data of MPCs using UV-Vis and TEM techniques are discussed. TEM images showed that functionalized spherical nanoclusters of 4.7 +/- 0.3 and 4.3 +/- 0.2 nm were produced. The particle sizes are uniform with a narrow size distribution. The morphology of Au(1 11) metal surface modified with MPCs was imaged using atomic force microscopy (AFM). The nanoparticle layer exhibits a distinct surface morphology, irregularly shaped domains with dimensions from 20 to 60 nm and root mean square heights of 2.401 nm. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.07.055
• 作为产物：
  描述：

  1,8-二碘辛烷 在 sodium hydrogensulfide 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 32.0h， 生成 4'-(8-mercaptooctyloxy)-2,2':6',2''-terpyridine
  参考文献：
  名称：

  Molecular self-assembled monolayers of ruthenium(II)-terpyridine dithiol complex on gold electrode and nanoparticles

  摘要：

  We describe the formation of stable dithiol-bifunctionalized Ru(II)-terpyridine monolayer onto gold electrode. The coverage-dependent behavior onto gold electrode has been studied by electrochemical technique. The stability, surface charge coverage, and electrontransfer kinetics were assessed by cyclic voltammetry. Functionalized monolayer-protected Au clusters (MPCs) were also prepared. The spectroscopic characterization data of MPCs using UV-Vis and TEM techniques are discussed. TEM images showed that functionalized spherical nanoclusters of 4.7 +/- 0.3 and 4.3 +/- 0.2 nm were produced. The particle sizes are uniform with a narrow size distribution. The morphology of Au(1 11) metal surface modified with MPCs was imaged using atomic force microscopy (AFM). The nanoparticle layer exhibits a distinct surface morphology, irregularly shaped domains with dimensions from 20 to 60 nm and root mean square heights of 2.401 nm. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.07.055

文献信息

• Preparation and characterization of gold nanoparticles with a ruthenium-terpyridyl complex, and electropolymerization of their pyrrole-modified metal nanocomposites
  作者：Masayuki Ito、Takashi Tsukatani、Hisashi Fujihara

  DOI：10.1039/b412406e

  日期：——

  The reduction of tetrachloroaurate with sodium borohydride in the presence of 2,2′:6′,2″-terpyridyloctanethiol gave terpyridine-functionalized gold nanoparticles (Tpy–Au, core size 2.0 nm). Metal complexation of Tpy–Au with ruthenium-terpyridyl trichloride, Ru(tpy)Cl3, led to new gold nanoparticles bearing the ruthenium-terpyridine complex (Ru–Tpy–Au, core size 5.5 nm) which showed a characteristic MLCT (metal-to-ligand charge transfer) band in the visible region at 483 nm due to the terpyridine-ruthenium complex and a plasmon resonance at ∼510 nm in the UV-vis spectrum. The redox behavior of Ru–Tpy–Au was studied by cyclic voltammetry. Surface modification of metal electrodes was performed by the electropolymerization of pyrrole-functionalized Ru–Tpy–Au nanoparticles (Pyr–Ru–Tpy–Au) which were obtained from the ligand-exchange reaction of Ru–Tpy–Au with ω-(N-pyrrolyl)decanethiol.

  在 2,2′:6′,2″-三吡啶辛硫醇存在下，用硼氢化钠还原四氯金酸酯，得到了三吡啶功能化金纳米粒子（Tpy-Au，核心尺寸 2.0 nm）。Tpy-Au 与三氯化钌-三吡啶（Ru(typy)Cl3）发生金属络合，产生了带有钌-三吡啶络合物的新金纳米粒子（Ru-Tpy-Au，核心尺寸为 5.在紫外可见光谱中，Ru-Tpy-Au 在 ∼ 510 nm 处显示出等离子共振。循环伏安法研究了 Ru-Tpy-Au 的氧化还原行为。Ru-Tpy-Au 与 ω-(N-吡咯基)癸硫醇的配体交换反应得到的吡咯官能化 Ru-Tpy-Au 纳米粒子（Pyr-Ru-Tpy-Au）通过电聚合作用对金属电极进行了表面修饰。
• Synthesis and redox behavior of biferrocenyl terpyridine-functionalized gold clusters
  作者：Hao-Wei Shih、Teng-Yuan Dong

  DOI：10.1016/j.inoche.2004.03.010

  日期：2004.5

  Spectroscopic and electrochemical characterizations of ferrocene- and biferrocene-functionalized terpyridine octanethiolate monolayer protected clusters were reported. The electrochemical data reveals that there is an interaction between redox centers. (C) 2004 Elsevier B.V. All rights reserved.
• Molecular self-assembled monolayers of ruthenium(II)-terpyridine dithiol complex on gold electrode and nanoparticles
  作者：Teng-Yuan Dong、Chienlin Huang、Chiao-Pei Chen、Ming-Cheng Lin

  DOI：10.1016/j.jorganchem.2007.07.055

  日期：2007.11

  We describe the formation of stable dithiol-bifunctionalized Ru(II)-terpyridine monolayer onto gold electrode. The coverage-dependent behavior onto gold electrode has been studied by electrochemical technique. The stability, surface charge coverage, and electrontransfer kinetics were assessed by cyclic voltammetry. Functionalized monolayer-protected Au clusters (MPCs) were also prepared. The spectroscopic characterization data of MPCs using UV-Vis and TEM techniques are discussed. TEM images showed that functionalized spherical nanoclusters of 4.7 +/- 0.3 and 4.3 +/- 0.2 nm were produced. The particle sizes are uniform with a narrow size distribution. The morphology of Au(1 11) metal surface modified with MPCs was imaged using atomic force microscopy (AFM). The nanoparticle layer exhibits a distinct surface morphology, irregularly shaped domains with dimensions from 20 to 60 nm and root mean square heights of 2.401 nm. (c) 2007 Elsevier B.V. All rights reserved.