tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine | 425367-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine
• 英文别名: tetrapyrido[3,2-a:2',3'-c:3'',3'-h:2''',3'''-j]acridine；TPAC；2,8,11,23,26-Pentazaheptacyclo[16.12.0.03,16.04,9.010,15.019,24.025,30]triaconta-1,3,5,7,9,11,13,15,17,19(24),20,22,25(30),26,28-pentadecaene
• CAS: 425367-07-3
• 化学式: C₂₅H₁₃N₅
• 分子量: 383.412
• InChiKey: IJGSJTHDLYTNPV-UHFFFAOYSA-N

物化性质

• 沸点：
  739.8±55.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 Ru(1,4,5,8-tetraazaphenanthrene)2Cl2 、 tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine 以 水 、 乙二醇 为溶剂， 以49%的产率得到[((1,4,5,8-tetraazaphenanthrene)2Ru)2(μ-tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine)](PF6)4
  参考文献：
  名称：

  Dinuclear Ru^IIPHEHAT and -TPAC Complexes:  Effects of the Second Ru^II Center on Their Spectroelectrochemical Properties

  摘要：

  Four novel dinuclear Ru-II compounds and, for comparison purposes, two corresponding mononuclear complexes containing the PHEHAT or TPAC ligand (PHEHAT = 1,10-phenanthrolino[5,6-b]-1,4,5,8,9,12-hexaazatriphenylene and TPAC = tetrapyrido[3,2-a:2',3'-c:3" ,2"-h:2''',3'''-j]acridine) have been synthesized and characterized. Conclusions on the effects of dinucleation of these two bridging ligands can be drawn only for the compounds for which the results demonstrate that the bridging ligand is involved in the first electrochemical reduction and lowest emission energy. The behavior of these complexes, which is not always predictable, is discussed, and the differences are highlighted in this work. Interestingly, all of the compounds are luminescent except one dinuclear species, [(phen)(2)Ru-mu-PHEHAT-Ru(TAP)(2)](4+), which does not luminesce in MeCN and BuCN at room temperature.

  DOI：

  10.1021/ic070224j
• 作为产物：
  描述：

  聚合甲醛 、 1,10-菲罗啉-5-氨基 在 盐酸 作用下， 反应 192.0h， 以59%的产率得到tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]acridine
  参考文献：
  名称：

  Tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]acridine (tpac): a new extended polycyclic bis-phenanthroline ligand

  摘要：

  A new heptacyclic planar molecule has been synthesized in a very efficient one-pot reaction from 5-aminophenanthroline. Ru(II) mono- and dinuclear complexes based on this new bridging ligand, Tpac, have been prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02131-1

文献信息

• Trinuclear ruthenium dendrons based on bridging PHEHAT and TPAC ligands
  作者：Kathleen Servaty、Cécile Moucheron、Andrée Kirsch-De Mesmaeker

  DOI：10.1039/c1dt10639b

  日期：——

  Novel polynuclear compounds, the trinuclear precursor complex cis-[(phen)2Ru(PHEHAT)]2Ru(CH3CN)2}6+4 and the trinuclear TPAC (tetrapyrido[3,2-a:2′,3′-c:3′′,2′-h:2′′′,3′′′-j]acridine) complex [(phen)2Ru(PHEHAT)]2Ru(TPAC)}6+5 have been prepared. Their electrochemistry and photophysics indicate that the 3MLCT (metal to ligand charge transfer) emissions involve the external Ru(PHEHAT)} moieties for both complexes and there is no spectro-electrochemical correlation. The trinuclear dendron with the TPAC ligand represents a key compound for future constructions of much larger species thanks to the TPAC that could bridge another polynuclear precursor. For decreasing the length of preparation of these compounds, microwave assisted syntheses have been tested and used not only for the targeted complexes but also for the precursors ((phen)2RuCl2, (phen)2Ru(phendione)}2+, (phen)2Ru(PHEHAT)}2+ (PHEHAT = 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene), (DMSO)4RuCl2), and for the bridging TPAC ligand itself. The microwave method allows a drastic decrease of the preparation times, especially in the case of the TPAC, from 8 days to 60 min.

  新型多核化合物，三核前体配合物 cis-[(phen)2Ru(PHEHAT)]2Ru(CH3CN)2}6+4 和三核 TPAC（四吡啶[3,2-a:2′,3′-c:3′′,2′-h:2′′′,3′′′-j]芴）配合物 [(phen)2Ru(PHEHAT)]2Ru(TPAC)}6+5 已经合成。它们的电化学和光物理特性表明，两个配合物的 3MLCT（金属到配体的电荷转移）发射涉及外部的 Ru(PHEHAT)} 组分，并且没有光谱-电化学相关性。带有 TPAC 配体的三核树枝状化合物代表了未来构建更大物种的关键化合物，因为 TPAC 可以连接另一个多核前体。为了缩短这些化合物的制备时间，采用了微波辅助合成方法，这不仅用于目标配合物，也用于前体 ((phen)2RuCl2、(phen)2Ru(phendione)}2+、(phen)2Ru(PHEHAT)}2+（PHEHAT = 1,10-苯并[5,6-b]1,4,5,8,9,12-六氮三苯并烯）、(DMSO)4RuCl2)以及连接的 TPAC 配体本身。微波法显著减少了制备时间，特别是在 TPAC 的情况下，从 8 天缩短到 60 分钟。
• Metal-based coordination complexes as photodynamic compounds and their use
  申请人：McFarland Sherri Ann

  公开号：US10766915B2

  公开（公告）日：2020-09-08

  Compositions of the invention include metal-based coordination complexes, which are preferably tunable photodynamic compounds. The compositions and complexes are useful as therapeutic agents and as in vivo diagnostic agents for treating or preventing diseases including those that involve hyperproliferating cells in their etiology, such as cancer. Compositions and complexes of the invention are further capable of destroying microbial cells, such as bacteria, fungi, and protozoa, and destroying viruses. The compositions and complexes are also capable of modulating cell function in other ways.

  本发明的组合物包括金属基配位复合物，它们最好是可调光动力化合物。本发明的组合物和配合物可用作治疗剂和体内诊断剂，用于治疗或预防疾病，包括在病因中涉及细胞过度增殖的疾病，如癌症。本发明的组合物和复合物还能消灭微生物细胞，如细菌、真菌和原生动物，并能消灭病毒。本发明的组合物和复合物还能以其他方式调节细胞功能。
• Synthesis and photophysics of a novel photocatalyst for hydrogen production based on a tetrapyridoacridine bridging ligand
  作者：Michael Karnahl、Christian Kuhnt、Frank W. Heinemann、Michael Schmitt、Sven Rau、Jürgen Popp、Benjamin Dietzek

  DOI：10.1016/j.chemphys.2011.11.027

  日期：2012.1

  Molecular photocatalysts allow for selectively tuning their function on a molecular level based on an in-depth understanding of their chemical and photophysical properties. This contribution reports the synthesis and photophysical characterization of the novel molecular photocatalyst [(tbbpy)(2)Ru(tpac)PdCl2](2+) RutpacPd (with tpac = tetrapyrido[3,2-a:2',3'-c:3 '',2 ''-h:2''',3'''-j]acridine) and its mononuclear building block. Furthermore, detailed photocatalytic activity measurements of RutpacPd are presented. The introduction of the tpac-ligand into the molecular framework offers a potential route to reduce the impact of water as compared to the well-studied class of RutpphzPd (with tpphz = tetrapyrido[3,2-a:2',3'-c:300,2 ''-h: 2''',3'''-j] phenazine) complexes. The distinct impact of water on the electron-transfer processes in tpphz-ligands stems from the possibility of water to form hydrogen bonds to the phenazine nitrogen atoms and will potentially reduced when replacing the phenazine by the acridine unit. The effect of this structural variation on the catalytic properties and the underlying ultrafast intramolecular charge transfer behavior will be discussed in detail. (C) 2011 Elsevier B. V. All rights reserved.
• METAL-BASED COORDINATION COMPLEXES AS PHOTODYNAMIC COMPOUNDS AND THEIR USE
  申请人：McFarland, Sherri Ann

  公开号：EP2976347B1

  公开（公告）日：2022-01-19
• [EN] METAL-BASED COORDINATION COMPLEXES AS PHOTODYNAMIC COMPOUNDS AND THEIR USE<br/>[FR] COMPLEXES DE COORDINATION A BASE DE MÉTAL EN TANT QUE COMPOSES PHOTODYNAMIQUES ET LEUR UTILISATION
  申请人：MCFARLAND SHERRI ANN

  公开号：WO2014145428A2

  公开（公告）日：2014-09-18

  Compositions of the invention include metal-based coordination complexes, which are preferably tunable photodynamic compounds. The compositions and complexes are useful as therapeutic agents and as in vivo diagnostic agents for treating or preventing diseases including those that involve hyperproliferating cells in their etiology, such as cancer. Compositions and complexes of the invention are further capable of destroying microbial cells, such as bacteria, fungi, and protozoa, and destroying viruses. The compositions and complexes are also capable of modulating cell function in other ways.