9,11,20,22-tetraaza-tetrapyridopentacene | 177528-16-4

• 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: 9,11,20,22-tetraaza-tetrapyridopentacene
• 英文别名: tatpp；9,11,20,22-Tetraazatetrapyrido[3,2-a:2',3'-c:3'',2''-l:2''',3'''-n]pentacene；4,10,13,19,23,29,32,38-octazanonacyclo[20.16.0.03,20.05,18.06,11.012,17.024,37.025,30.031,36]octatriaconta-1(22),2,4,6(11),7,9,12(17),13,15,18,20,23,25(30),26,28,31(36),32,34,37-nonadecaene
• CAS: 177528-16-4
• 化学式: C₃₀H₁₄N₈
• 分子量: 486.495
• InChiKey: WUOAHAAXPJSZCT-UHFFFAOYSA-N

物化性质

• 密度：
  1.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9,11,20,22-tetraaza-tetrapyridopentacene 在 氢气 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Tuning the reduction of 9,11,20,22-tetraaza-tetrapyridopentacene (TATPP)

  摘要：

  Organic molecules capable of storing and shuttling multiple electrons are desirable for various applications including solar energy conversion, small molecule activation, and water splitting. Here, we demonstrate the ability to photochemically control the reduction of 9,11,20,22-tetraaza-tetrapyridopentacene (TATPP) to form either TATPPH(2) or [TATPPH](-), both of which display distinct optical and electrochemical properties, thus providing a rationale for their use in various applications. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.142
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 1,2,4,5-benzenetetraamine tetrahydrochloride 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到9,11,20,22-tetraaza-tetrapyridopentacene
  参考文献：
  名称：

  Tuning the reduction of 9,11,20,22-tetraaza-tetrapyridopentacene (TATPP)

  摘要：

  Organic molecules capable of storing and shuttling multiple electrons are desirable for various applications including solar energy conversion, small molecule activation, and water splitting. Here, we demonstrate the ability to photochemically control the reduction of 9,11,20,22-tetraaza-tetrapyridopentacene (TATPP) to form either TATPPH(2) or [TATPPH](-), both of which display distinct optical and electrochemical properties, thus providing a rationale for their use in various applications. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.142

文献信息

• Self-assembled [2]catenane in trapezoidal metallacycles with [Cp*Ir]-corners
  作者：Naifang Liu、Sheng-Li Huang、Xiaogang Liu、He-Kuan Luo、T. S. Andy Hor

  DOI：10.1039/c7cc08009c

  日期：——

  The metallacyclic assembly of [2]catenanes was investigated by optimising the cavity size of trapezoidal rings.

  [2]猫环的金属环组装是通过优化梯形环的空腔尺寸来研究的。
• Photochemical Two-Electron Reduction of a Dinuclear Ruthenium Complex Containing a Bent Tetraazatetrapyridopentacene Bridging Ligand: Pushing Up the LUMO for Storing More Energy
  作者：Shreeyukta Singh、Norma R. de Tacconi、N.R.G. Diaz、Reynaldo O. Lezna、Jackeline Muñoz Zuñiga、Kenneth Abayan、Frederick M. MacDonnell

  DOI：10.1021/ic2006698

  日期：2011.10.3

  The synthesis and characterization of a ditopic bridging ligand, 9,12,21,22-tetraazatetrapyrido[3,2-a:2′,3′-c:3″2″-m:2′′′,3′′′-o]pentaphene (tatppα) and its dinuclear ruthenium complex, [(phen)2Ru(tatppα)Ru(phen)2][PF6]4 (14+), are described. The tatppα ligand is structurally very similar to 9,10,20,33-tetraazatetrapyrido[3,2-a:2′,3′-c:3″,2″-l:2′′′,3′′′-n]pentacene (tatppβ), except that, instead of

  对位桥接配体9,12,21,22-四氮杂叠氮基[3,2- a：2'，3'- c：3“ 2” -m：2'''，3'''的合成与表征-描述了邻邻五苯芬（tatppα）及其双核钌络合物[[（phen）2 Ru（tatppα）Ru（phen）2 ] [PF 6 ] 4（1 4+）。tatppα配体在结构上与9,10,20,33-四氮杂叠氮基[3,2- a：2'，3'- c：3“，2” -l：2'''，3'''- ñ]并五苯（tatppβ），不同之处在于，tatppα代替线性四氮杂并五苯骨架，在中心苯环周围具有邻位（或α）取代图案，导致120°弯曲。复杂1个4+节目tatppα基于在-0.73减量和-1.14 V相对于银/氯化银/饱和KCl和具有示出了典型的Ru的吸收光谱II dπ→苯状π*金属到配体的电荷转移过渡为中心在〜450 nm。在乙腈中，可见光辐射为1 4+在三乙胺的存在下，导致吸收光谱的
• Synthesis, DNA Cleavage Activity, Cytotoxicity, Acetylcholinesterase Inhibition, and Acute Murine Toxicity of Redox‐Active Ruthenium(II) Polypyridyl Complexes
  作者：Nagham Alatrash、Eugenia S. Narh、Abhishek Yadav、Mahn‐Jong Kim、Thamara Janaratne、James Gabriel、Frederick M. MacDonnell

  DOI：10.1002/cmdc.201700240

  日期：2017.7.6

  Four mononuclear [(L-L)2 Ru(tatpp)]2+ and two dinuclear [(L-L)2 Ru(tatpp)Ru(L-L)2 ]4+ ruthenium(II) polypyridyl complexes (RPCs) containing the 9,11,20,22-tetraazatetrapyrido[3,2-a:2',3'-c:3'',2''-l:2''',3'''-n]pentacene (tatpp) ligand were synthesized, in which L-L is a chelating diamine ligand such as 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4

  四个单核[（LL）2 Ru（tatpp）] 2+和两个双核[（LL）2 Ru（tatpp）Ru（LL）2] 4+钌（II）聚吡啶基配合物（RPC），包含9,11,20合成了22,4-四氮杂萘并[3,2-a：2'，3'-c：3''，2''-1：2'''，3'''-n]并五苯（tatpp）配体LL是螯合的二胺配体，例如2,2'-联吡啶（bpy），1,10-菲咯啉（phen），3,4,7,8-四甲基-1,10-菲咯啉（Me4 phen）或4， 7-二苯基-1,10-菲咯啉（Ph2 phen）。这些Ru-tatpp类似物均在pH 7下与适度的还原剂（如谷胱甘肽（GSH））进行还原反应，并筛选了几种结构相关但无氧化还原活性的RPC，以检测其DNA裂解活性，细胞毒性，乙酰胆碱酯酶（ AChE）抑制和急性小鼠毒性，并就其氧化还原活性和亲脂性检查了它们的活性。在存在GSH的情况下，所有具有氧化还原活性的R
• Primary Photoinduced Processes in Bimetallic Dyads with Extended Aromatic Bridges. Tetraazatetrapyridopentacene Complexes of Ruthenium(II) and Osmium(II)
  作者：Claudio Chiorboli、Sandro Fracasso、Marcella Ravaglia、Franco Scandola、Sebastiano Campagna、Kelly L. Wouters、Rama Konduri、Frederick M. MacDonnell

  DOI：10.1021/ic051062z

  日期：2005.11.1

  tatpp ligand-centered (LC) triplet in the case of Ru(II); a metal-to-ligand charge-transfer (MLCT) triplet state in the case of Os(II). The excited-state kinetics is strongly solvent-dependent. In the Ru(II) system, the formation and decay of the LC state take place, respectively, in 25 ps and ca. 5 ns in CH3CN and in 0.5 ps and 1.3 micros in CH2Cl2. These solvent effects can be rationalized on the

  双核配合物[（phen）2M（tatpp）M（phen）2] 4+的光物理性质，其中M = Ru或Os，phen = 1,10-菲咯啉，tatpp = 9,11,20,22-四氮杂叠氮灵[3,2-a：2'3'-c：3''，2''-l：2'''，3''']并五苯在乙腈和二氯甲烷中的飞秒和纳秒时间分辨能力得到了研究技术。结果表明，不同金属的配合物具有不同类型的最低激发态：在Ru（II）的情况下，以tatpp配体为中心的（LC）三重态；在Os（II）的情况下，金属到配体的电荷转移（MLCT）三重态。激发态动力学强烈依赖于溶剂。在Ru（II）系统中，LC状态的形成和衰减分别以25 ps和ca的速度发生。在CH3CN中为5 ns，在CH2Cl2中为0.5 ps和1.3 micros。这些溶剂效应可以根据LC状态通过上层MLCT状态的热激活衰减来合理化。在Os（II）系统中，MLCT状态的形成和衰减分别在CH3CN中以3
• Quadruple electron storage using visible light with nitrogen-heterocycles under metal-free conditions
  作者：J.M. Aslan、M. Yousufuddin、D.J. Boston、F.M. MacDonnell

  DOI：10.1016/j.ica.2016.06.025

  日期：2017.1

  A byproduct of the synthesis of 9,11,20,22-tetra-aza-tetrapyrido[3,2-a:2 ' 3 '-c:3 '',2 ''-I:2 ''',3 ''']-pentacene (tatpp) is the symmetrical dimer ditatpp, which is linked by a carbon-carbon bond along the central benzene ring. The structure of the dimer has been determined by X-ray crystallography and reveals a dihedral angle of 73 degrees between the two tatpp units, which is likely due lone pair repulsion on the adjacent aza nitrogens on each tatpp unit. Because of this non-planar geometry, this ditatpp dimer is freely soluble in organic solvents, such as ethanol, very much unlike the tatpp ligand, which is sparingly soluble in all common solvents. Photolysis of ditatpp with visible light in the presence of sacrificial donors, such as triethylamine, results in multi-electron reduction on each of the tatpp units, as determined by absorption spectroscopy. As the tatpp units appear to function independently of one another, and each tatpp unit is reduced by two electrons and is doubly protonated in the final compound, the photoreduction results in a net storage of 4 electrons in the fully reduced species. (C) 2016 Elsevier B.V. All rights reserved.