2-[4-2-(trimethylsiyl)ethynylphenyl]-1H-imidazo[4,5-f][1,10]phenanthroline | 1262284-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[4-2-(trimethylsiyl)ethynylphenyl]-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-{4-[2-(trimethylsilyl)ethynyl]phenyl}-1H-imidazo[4,5-f ][1,10]phenanthroline；2-{4-[1'-(2'-trimethylsilyl)ethynyl]phenyl}imidazo[4,5-f]-1,10-phenanthroline；TMS-EPIP；2-[4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenyl]ethynyl-trimethylsilane
• CAS: 1262284-78-5
• 化学式: C₂₄H₂₀N₄Si
• 分子量: 392.535
• InChiKey: AKIGUKMUUREGKD-UHFFFAOYSA-N

物化性质

• 沸点：
  596.3±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 2-[4-2-(trimethylsiyl)ethynylphenyl]-1H-imidazo[4,5-f][1,10]phenanthroline 以 水 、 乙二醇 为溶剂， 反应 0.33h， 以85.9%的产率得到[Ru(bpy)₂(p-TEPIP)]*(ClO₄)₂
  参考文献：
  名称：

  钌(II)配合物及其制备方法及其作为细胞荧 光染料的应用

  摘要：

  本发明公开了一种钌(II)配合物，其结构如下所示：；也公开了该化合物的制备方法，包括步骤：先以邻菲啰啉5,6‑二酮与为原料制备X‑RPIP，再以X‑RPIP与cis‑Ru(L)2Cl2为原料制备得产物。或者，先以X‑BrPIP与为原料制备X‑RPIP，再以X‑RPIP与cis‑Ru(L)2Cl2为原料制备得产物。或者，先以钌前体Ru(L)2Cl2与X‑ R’’’PIP为原料反应制得Ru(L)2(X‑ R’’’PIP)2+，再以Ru(L)2(X‑ R’’’PIP)2+、为原料制备得到产物。本发明的合成方法简单，尤其所合成的Λ‑[Ru(bpy)2(p‑BEPIP)]2+对活细胞无毒、迅速跨膜、荧光颜色强易观察且不易淬灭、荧光激发与发射波段不重叠并且可以再细胞核富集。

  公开号：

  CN103709202B
• 作为产物：
  描述：

  1,10-菲罗啉 在 硫酸 、 ammonium acetate 、 硝酸 、 potassium bromide 作用下， 以 溶剂黄146 为溶剂， 生成 2-[4-2-(trimethylsiyl)ethynylphenyl]-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Synthesis and evaluation of the europiumIII and zincII complexes as luminescent bioprobes in high content cell-imaging analysis

  摘要：

  Novel phenanthroline derivatives and their europium(III) and zinc(II) complexes have been prepared in up to 92%. In contrast to the stable zinc complexes, the europium compounds exhibit a strong luminescence in THF solution. However, quenching of the emission is observed in DMSO indicating complete dissociation of the complexes back to free ligands in this solvent. H-1 NMR studies of the Eu(III)-complexes 5 and 6 also confirmed the existence of different states depending on the solvent used. Moreover, it was found that compound 5 is stable in EtOH-PBS solutions: here a strong signal in the emission spectra corresponding to the europium ion was detected. No spectral changes were observed for the zinc(II) complexes, they were shown to be stable in the media. These metal complexes can be used as fluorescence markers for the diagnosis of oesophageal squamous carcinoma (OE21) cells at low concentrations. Cell images were acquired using the compounds 5, 7-9 as luminescent agents. The first images were taken already after 20 min incubation time at a very low concentration range (0.7-1.6 mu M). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2011.08.023

文献信息

• Synthesis of Ruthenium Tris‐Diimine Photosensitizers Substituted by Four Methylphosphonate Anchoring Groups for Dye‐Sensitized Photoelectrochemical Cell Applications
  作者：Nicolas Queyriaux、Emmanouil Giannoudis、Jean‐François Lefebvre、Vincent Artero、Murielle Chavarot‐Kerlidou

  DOI：10.1002/ejic.201900151

  日期：2019.4.24

  The design and synthesis of ruthenium tris‐diimine photosensitizers appropriately functionalized to be (i) anchored onto transparent conductive oxides (TCO) and (ii) covalently coupled with a water‐splitting catalyst represents an important target for solar fuel production in dye‐sensitized photoelectrochemical cells (DS‐PECs). In this study, two different synthetic routes to prepare heteroleptic [Ru(4

  适当地功能化为（i）固定在透明导电氧化物（TCO）上和（ii）与水分解催化剂共价偶联的钌三二亚胺光敏剂的设计与合成代表了染料敏化光电化学中太阳能燃料生产的重要目标单元（DS-PEC）。在这项研究中，评估了两种不同的制备杂合[Ru（4,4'-（CH 2 PO 3 Et 2）2 -bpy）2（N ^ N）]（PF 6）2配合物的合成途径，范围和包括半夹心η有机金属途径的限制6芳烃钌络合物作为合成中间体正在得到专门研究。报道了根据第三二亚胺N ^ N配体的性质而变化的一系列新颖结构的光谱学和电化学表征。
• Energy Transfer in a Hybrid Ir^IIICarbene-Pt^IIAcetylide Assembly for Efficient Hydrogen Production
  作者：Zhen-Tao Yu、Yong-Jun Yuan、Xin Chen、Jian-Guang Cai、Zhi-Gang Zou

  DOI：10.1002/chem.201500193

  日期：2015.7.6

  carbene‐based unit appended to a platinum terpyridine acetylide unit, representing a new IrIII–PtII structural motif, was designed and developed to act as an active species for photocatalytic hydrogen production. The results also suggested that a light‐harvesting process is essential to realize the solar‐to‐fuel conversion in an artificial system as illustrated in the natural photosynthetic system.

  设计并开发了一种新的杂金属超分子络合物，由铱卡宾基单元和铂吡啶吡啶乙炔单元附加而成，代表新的Ir III -Pt II结构基序，可作为光催化制氢的活性物种。结果还表明，光捕获过程对于实现人工系统中的太阳能转化为燃料至关重要，如自然光合作用系统所示。
• Luminescent Ruthenium Tripod Complexes: Properties in Solution and on Conductive Surfaces
  作者：Srinidhi Ramachandra、Klaus C. Schuermann、Fabio Edafe、Peter Belser、Christian A. Nijhuis、William F. Reus、George M. Whitesides、Luisa De Cola

  DOI：10.1021/ic1002868

  日期：2011.3.7

  Two luminescent ruthenium complexes containing tripod-type end groups linked through a rigid spacer to a phenanthroline derivative, able to confer an axial geometry to the complexes, are described. One of the compounds is functionalized with thioacetate groups in order to link the metal complex to metallic surfaces. The photophysical and electrochemical behavior of the complexes are studied in solution and on conductive substrates and, furthermore, self-assembled monolayers are investigated in a junction using gold and an indium gallium eutectic, as electrodes, and by time-resolved confocal microscopy. The results show that the complexes form very stable and well-ordered monolayers because of the tripod system, which can anchor the complex almost perpendicular to the surfaces.
• Simple but powerful: Phenanthroline-based small molecules for cellular imaging and cancer screening
  作者：Natalia N. Sergeeva、Marion Donnier-Marechal、Gisela M. Vaz、Anthony M. Davies、Mathias O. Senge

  DOI：10.1016/j.bmcl.2011.06.051

  日期：2011.8

  A two-step synthetic procedure gives highly fluorescent phenanthroline molecular probes. The compounds localize in the endoplasmic reticulum and their potential as bioactive probes was evaluated. The materials are quickly taken up by living cells within 5 min. Preliminary in vitro studies have shown that these compounds are selective to esophageal cancer cells and can be used as selective markers in intracellular cancer diagnostics. The materials show a remarkable cytotoxicity towards cancer cells vs normal as 7-1. (C) 2011 Elsevier Ltd. All rights reserved.