9,10-diamino-1,4,5,8-tetraazaphenanthrene | 79790-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9,10-diamino-1,4,5,8-tetraazaphenanthrene
• 英文别名: Pyrazino[2,3-f]quinoxaline-5,6-diamine；pyrazino[2,3-f]quinoxaline-5,6-diamine
• CAS: 79790-36-6
• 化学式: C₁₀H₈N₆
• 分子量: 212.214
• InChiKey: WPNITXFHYRBRCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9,10-diamino-1,4,5,8-tetraazaphenanthrene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 三叔丁基膦 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  유기 화합물, 유기 광전자 소자 및 표시 장치

  摘要：

  这是关于有机光电子元件和显示器件中包含的有机化合物，其化学式表示为1。在化学式1中，L到L，Ar，Ar，n1，n2，m1到m4如规范中所述。

  公开号：

  KR20170124412A
• 作为产物：
  描述：

  1,3,5-三氯苯 在 甲醇 、 硫酸 、 三氧化硫 、 氨 、 sodium 、 potassium nitrate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 9,10-diamino-1,4,5,8-tetraazaphenanthrene
  参考文献：
  名称：

  Synthesis and Electrochemical and Theoretical Studies of V-Shaped Donor−Acceptor Hexaazatriphenylene Derivatives for Second Harmonic Generation

  摘要：

  In this article we describe novel synthetic strategies toward well-defined disubstituted conjugated hexaazatriphenylene (HAT) derivatives The systems are designed as novel V-shaped chromophores displaying C-2 symmetry suitable for nonlinear optical investigations Different donor moieties and linkers have been used in order to tune the electrochemical properties as well as the absorption spectra of the novel HAT derivatives mu beta values as high as 1010 x 10(-48) esu have been obtained for a derivative containing the electron-rich dibutyl-amino moiety Theoretical calculations have been performed showing a reasonable agreement with the experimental results and supporting the two-dimensional NLO character of these chromophores

  DOI：

  10.1021/jo101311v

文献信息

• Towards the Development of Photo‐Reactive Ruthenium(II) Complexes Targeting Telomeric G‐Quadruplex DNA
  作者：Justin Weynand、Aurélie Diman、Michaël Abraham、Lionel Marcélis、Hélène Jamet、Anabelle Decottignies、Jérôme Dejeu、Eric Defrancq、Benjamin Elias

  DOI：10.1002/chem.201804771

  日期：2018.12.20

  characterization of new ruthenium(II) complexes aimed at targeting G‐quadruplex DNA is reported. Importantly, these complexes are based on oxidizing 1,4,5,8‐tetraazaphenanthrene (TAP) ancillary ligands known to favour photo‐induced electron transfer (PET) with DNA. The photochemistry of complexes 1–4 has been studied by classical methods, which revealed two of them to be capable of photo‐abstracting an electron

  报道了针对G-四链体DNA的新钌（II）配合物的设计和表征。重要的是，这些络合物是基于氧化1,4,5,8-四氮杂菲（TAP）辅助配体而形成的，这些配体有利于DNA的光诱导电子转移（PET）。复合物的光化学1 - 4已通过经典方法进行了研究，发现其中两种方法能够从鸟嘌呤中吸收电子。从通过发光，圆二色性，生物层干涉和表面等离振子共振实验研究与DNA的相互作用中，我们证明了这些复合物对端粒G-四链体DNA的选择性高于双链体DNA。已对这些复合物进行了初步的生物学研究：其中两个显示出对端粒酶阴性的U2OS骨肉瘤细胞具有显着的光细胞毒性，而在相同光药物浓度下，在黑暗中观察到极低的死亡率。
• 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。
• Targeting G‐Rich DNA Structures with Photoreactive Bis‐Cyclometallated Iridium(III) Complexes
  作者：Justin Weynand、Hughes Bonnet、Frédérique Loiseau、Jean‐Luc Ravanat、Jérôme Dejeu、Eric Defrancq、Benjamin Elias

  DOI：10.1002/chem.201902183

  日期：2019.10

  The synthesis and characterisation of three novel iridium(III) bis-cyclometallated complexes is reported. Their photophysics have been fully characterised by classical methods and revealed charge-transfer (CT) and ligand-centred (LC) transitions. Their ability to selectively interact with G-quadruplex telomeric DNA over duplex DNA has been studied by circular dichroism (CD), bio-layer interferometry

  报道了三种新型铱（III）双环金属化配合物的合成与表征。它们的光物理特性已通过经典方法充分表征，并显示出电荷转移（CT）和以配体为中心（LC）的跃迁。通过圆二色性（CD），生物层干涉法（BLI）和表面等离振子共振（SPR）分析，研究了它们与G-四链体端粒DNA在双链DNA上选择性相互作用的能力。有趣的是，其中一种复合物能够促进鸟嘌呤DNA碱基的光诱导电子转移（PET），进而导致端粒序列发生氧化损伤（例如8-氧代鸟嘌呤的形成）。据我们所知，这是对具有G-四链体端粒DNA的高光氧化性双环金属化铱（III）配合物的首次研究。
• Dendritic Tetranuclear Ru(II) Complexes Based on the Nonsymmetrical PHEHAT Bridging Ligand and Their Building Blocks:  Synthesis, Characterization, and Electrochemical and Photophysical Properties
  作者：Julien Leveque、Benjamin Elias、Cécile Moucheron、Andrée Kirsch-De Mesmaeker

  DOI：10.1021/ic048941q

  日期：2005.1.1

  Dinuclear and tetranuclear Ru(II) compounds 1, 2, 3, and 4 based on the PHEHAT ligand (PHEHAT = 1,10-phenanthrolino[5,6-b]-1,4,5,8,9,12-hexaazatriphenylene) are prepared and characterized on the basis of the data for other related mononuclear species. Their electrochemical and spectroscopic behaviors are discussed. The nonspectroelectrochemical correlation obtained for 1, 2, 3, and 4 is explained on

  基于PHEHAT配体的双核和四核Ru（II）化合物1、2、3和4（PHEHAT = 1,10-菲咯啉[5,6-b] -1,4,5,8,9,12-六氮杂三苯并）是根据其他相关单核物种的数据制备和表征的。讨论了它们的电化学和光谱行为。在这些数据的基础上解释了针对1、2、3和4所获得的非光谱电化学相关性。从发射行为可以得出结论，内部能量在3和4中从铁心传递到外围金属单元。
• ORGANIC COMPOUND, ORGANIC LIGHT-EMITTING ELEMENT, DISPLAY APPARATUS, PHOTOELECTRIC CONVERSION APPARATUS, ELECTRONIC APPARATUS, LIGHTING DEVICE, AND MOVING OBJECT
  申请人：CANON KABUSHIKI KAISHA

  公开号：US20220173332A1

  公开（公告）日：2022-06-02

  An organic compound represented by formula [1]: where in formula [1], R 1 to R 6 are each independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, and other substituents having a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, at least one of R 1 to R 6 is one of the other substituents, at least any one of R 1 and R 2 is a hydrogen atom or a hydrocarbon group, at least any one of R 3 and R 4 is a hydrogen atom or a hydrocarbon group, and at least any one of R 5 and R 6 is a hydrogen atom.

  这是一种有机化合物，其化学式为[1]：其中，在化学式[1]中，R1至R6各自独立地选自由氢原子、烃基和其他取代或未取代的烷基、取代或未取代的芳基或取代或未取代的杂环基组成的群体，至少其中一个为其他取代基，至少R1和R2中的任意一个为氢原子或烃基，至少R3和R4中的任意一个为氢原子或烃基，至少R5和R6中的任意一个为氢原子。