4-(2-pyridyl)-1H-1,2,3-triazol-1-ylferrocene | 1310414-65-3

• 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-(2-pyridyl)-1H-1,2,3-triazol-1-ylferrocene
• 英文别名: cyclopenta-1,3-diene;2-(1-cyclopenta-1,4-dien-1-yltriazol-4-yl)pyridine;iron(2+)
• CAS: 1310414-65-3
• 化学式: C₁₇H₁₄FeN₄
• 分子量: 330.172
• InChiKey: SZVQONOFWVQNSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4-(2-pyridyl)-1H-1,2,3-triazol-1-ylferrocene 以 氯仿 为溶剂， 以73 %的产率得到fac-[(2-(1-ferrocenyl-1H-1,2,3-triazol-4-yl)pyridine)Re(CO)₃Cl]
  参考文献：
  名称：

  具有 1,2,3-三唑基吡啶螯合部分的单金属 Re(I) 和异双金属 Re(I)/Fe(II) 配合物的合成、表征和生物学评价

  摘要：

  生物有机金属配合物引起了人们极大的兴趣，并显示出在癌症治疗和诊断以及生物成像剂（其中一些充当治疗诊断剂）方面的潜在应用前景。制备了一系列新型二茂铁、苯并咪唑并[1,2- a ]喹啉和荧光素二齿吡啶基-1,2,3-三唑和2,2'-二吡啶胺衍生物及其三羰基铼( I )配合物，并通过NMR对其进行了充分表征、单晶 X 射线衍射、紫外-可见光和生物相关条件下的荧光光谱。荧光素和苯并咪唑并[1,2- a ]喹啉配体及其与Re( I) 显示了与 ds-DNA/RNA 和 HSA 的相互作用，通过热变性测量、荧光和圆二色性滴定进行表征。结合常数表明，Re( I ) 的添加增加了荧光素的亲和力，但降低了苯并咪唑并[1,2- a ]喹啉的亲和力。Re( I )的络合对荧光素和苯并咪唑并[1,2- a ]喹啉配体在生物大分子结合时的荧光灵敏度产生相反的影响，Re( I )荧光素络合物的发射被DNA/RNA或HSA强烈猝灭，而发射Re(

  DOI：

  10.1039/d3dt01070h
• 作为产物：
  描述：

  2-乙炔基吡啶 、 1-azidoferrocene 在 CuSO₄*5H₂O 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以81%的产率得到4-(2-pyridyl)-1H-1,2,3-triazol-1-ylferrocene
  参考文献：
  名称：

  二茂铁-三唑-吡啶三联体的合成，结构表征以及电化学和光学性质

  摘要：

  介绍了二茂铁-三唑-吡啶三联体3和5的合成以及电化学，光学和阳离子传感特性。叠氮二茂铁1和1,1'-二叠氮二茂铁4与2-乙炔基吡啶进行“点击”反应，分别以81％和68％的产率得到三单元组3和5。在不断增加的Zn 2 +，Ni 2 +，Cd 2 +，Hg 2+和Pb 2+的存在下在CH 3 CN中进行的电化学研究金属阳离子，表明相应于波形的二茂铁/二茂铁鎓氧化还原对被阳极由70-130毫伏偏移为三单元组3和167-214毫伏三联体5。在Zn 2+存在下，发现二茂铁氧化波的最大位移为5。此外，与这些金属阳离子络合后，3和5的吸收光谱的低能带发生红移（Δλ= 5-10 nm）。化合物3和5以及配合物[ 3 2 ·Zn] 2+的晶体结构已经通过单晶X射线方法确定。1个已经进行了1 H NMR研究以及密度泛函理论计算，以获得有关络合过程中涉及的结合位点的信息。

  DOI：

  10.1021/ic200745q

文献信息

• Ferrocene-appended ligands for use in spin crossover-redox “hybrid” complexes of iron(<scp>ii</scp>) and cobalt(<scp>ii</scp>)
  作者：Hayley S. Scott、Christopher J. Gartshore、Si-Xuan Guo、Boujemaa Moubaraki、Alan M. Bond、Stuart R. Batten、Keith S. Murray

  DOI：10.1039/c4dt02126f

  日期：——

  Structural, magnetic and electrochemical data are described for trans-[Fe^II(FTP)₂(NCS)₂], [Co^II(FTTP)₂](ClO₄)₂·2(MeCN) and [Fe^II(FTTP)₂](ClO₄)₂·Et₂O where FTP and FTTP are ferrocene-appended chelators.

  介绍了三种化合物的结构、磁性和电化学数据：[Fe^II(FTP)₂(NCS)₂](反式构型)、[Co^II(FTTP)₂](ClO₄)₂·2(MeCN)和[Fe^II(FTTP)₂](ClO₄)₂·Et₂O，其中FTP和FTTP是ferrocene-appended螯合剂。
• Spin crossover in iron(<scp>ii</scp>) complexes with ferrocene-bearing triazole-pyridine ligands
  作者：Tania Romero-Morcillo、Francisco Javier Valverde-Muñoz、Lucía Piñeiro-López、M. Carmen Muñoz、Tomás Romero、Pedro Molina、José A. Real

  DOI：10.1039/c5dt03084f

  日期：——

  Thermal- and light-induced spin crossover properties of two iron(ii) complexes derived from a ferrocene-appended triazole-pyridine ligand are described.

  本文描述了两种铁（II）配合物的热和光诱导的自旋交替性质，这些配合物源自于一个附加了三唑-吡啶配体的二茂铁。
• Heterotri‐ and Heteropentanuclear Copper(I)–Ferrocenyl Complexes Assembled through a “Click” Strategy: A Structural, Electrochemical, and Spectroelectrochemical Investigation
  作者：Sinja Manck、Marc Röger、Margarethe van der Meer、Biprajit Sarkar

  DOI：10.1002/ejic.201601075

  日期：2017.1.10

  (Fe–Cu–Fe) and a heteropentanuclear (Fe–Cu–Fe–Cu–Fe) complex. All complexes were characterized by 1H and 13C NMR spectroscopy and by mass spectrometry, and the heteropentanuclear complex was characterized by single-crystal X-ray diffraction. Electrochemistry and UV/Vis/NIR spectroelectrochemistry were used to investigate the redox properties of the complexes and to determine the site of electron transfer

  二茂铁部分具有明确的氧化还原行为和取代潜力，非常适合组装多核复合物。利用“点击”策略，我们在此展示了单取代和双取代的吡啶基-三唑基-二茂铁单元。然后使用“吡啶基-三唑基”螯合口袋螯合到额外包含 dppf [dppf = 1,1'-(二苯基膦基)二茂铁]的铜（I）中心，其具有额外的二茂铁部分。该策略提供了异三核 (Fe-Cu-Fe) 和异五核 (Fe-Cu-Fe-Cu-Fe) 复合物。所有配合物均通过 1 H 和 13 C NMR 光谱和质谱进行表征，杂戊核配合物通过单晶 X 射线衍射表征。电化学和紫外/可见光/近红外光谱电化学用于研究复合物的氧化还原特性并确定电子转移的位置。这里展示的结果显示了“点击”衍生配体在生成异多核组件方面的潜力，以及二茂铁在这些组件中作为刚性氧化还原活性单元的潜力。
• Palladium(II) Complexes of Readily Functionalized Bidentate 2-Pyridyl-1,2,3-triazole “Click” Ligands: A Synthetic, Structural, Spectroscopic, and Computational Study
  作者：Kelly J. Kilpin、Emma L. Gavey、C. John McAdam、Christopher B. Anderson、Samuel J. Lind、Courtney C. Keep、Keith C. Gordon、James D. Crowley

  DOI：10.1021/ic200789b

  日期：2011.7.4

  The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes, the CuAAC "click" reaction is currently receiving considerable attention as a mild, modular method for the generation of functionalized ligand scaffolds. Herein we show that mild one-pot "click" methods can be used to readily and rapidly synthesize a family of functionalized bidentate 2-pyridyl-1,2,3-triazole ligands, containing electrochemically, photochemically, and biologically active functional groups in good to excellent yields (47-94%). The new ligands have been fully characterized by elemental analysis, HR-ESI-MS, IR, H-1 and C-13 NMR and in three cases by X-ray crystallography. Furthermore we have demonstrated that this family of functionalized "click" ligands readily form bis-bidentate Pd(II)/complexes. Solution studies, X-ray crystallography, and density functional theory (DFT) calculations indicate that the Pd(II) complexes formed with the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine series of ligands are more stable than those formed with the [4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine "click" ligands.
• Rhenium(I) complexes of readily functionalized bidentate pyridyl-1,2,3-triazole “click” ligands: A systematic synthetic, spectroscopic and computational study
  作者：Tae Y. Kim、Anastasia B.S. Elliott、Karl J. Shaffer、C. John McAdam、Keith C. Gordon、James D. Crowley

  DOI：10.1016/j.poly.2012.05.003

  日期：2013.3

  A family of electronically tuned fac-Re(CO)(3)Cl pyridyl-1,2,3-triazole complexes have been synthesized by refluxing methanol solutions of [Re(CO)(5)Cl] and the substituted 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine ligands (pytri-R). The resulting rhenium(I) complexes were characterised by elemental analysis, HR-ESMS, IR, H-1 and C-13 NMR and in one case the molecular structure was confirmed by X-ray crystallography. The electronic structure of this family of fac-[(pytri-R)Re(CO)(3)Cl] complexes was probed using UV-Vis, Raman and emission spectroscopy and cyclic voltammetry techniques. The complexes show intense absorptions in the visible region, comprising strong pi -> pi* and metal-to-ligand charge-transfer (MLCT) transitions, which were modelled using time-dependent density functional theory (TD-DFT). Interestingly, the MLCT transition energy and the emission maxima are unaffected by the nature of the R substituent on the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine ligand indicating that the 1,2,3-triazoyl unit is acting as an electronic insulator. The emission lifetimes of the complexes are modestly dependent on the nature of the 1,2,3-triazole substituent, with the conjugated complexes displaying longer lifetimes than the non-conjugated ones. The shorter lifetimes for complexes with non-conjugated ligands are attributed to the "free-rotor" effect which allows molecules to relax through non-radiative pathways. In this case, the freely rotating CH2 group located between the triazole and the R group causes the decrease in excited lifetime. The electrochemistry of all examples is defined by irreversible Re oxidation and triazole based ligand reduction processes. The nitro substituted complexes show additional nitrobenzene type reduction features. Similarly, the ferrocenyl substituted complex displays the expected reversible one electron oxidation process. Consistent with the spectroscopic data, the position of the oxidation and reduction processes are essentially unaffected by the electronic nature of the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine substituent. (C) 2012 Elsevier Ltd. All rights reserved.