2,5-di-[2′,4′,6′-(tri-methyl)-anilino]-1,4-benzoquinone | 1309444-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-di-[2′,4′,6′-(tri-methyl)-anilino]-1,4-benzoquinone
• 英文别名: 2,5-bis(mesitylamino)cyclohexa-2,5-diene-1,4-dione；2,5-di-(2,4,6-trimethylanilino)-1,4-benzoquinone；2,5-Bis(2,4,6-trimethylanilino)cyclohexa-2,5-diene-1,4-dione；2,5-bis(2,4,6-trimethylanilino)cyclohexa-2,5-diene-1,4-dione
• CAS: 1309444-29-8
• 化学式: C₂₄H₂₆N₂O₂
• 分子量: 374.483
• InChiKey: XADQIYXRNJKEQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十羰基二铼 、 2,5-di-[2′,4′,6′-(tri-methyl)-anilino]-1,4-benzoquinone 、 乙腈 以 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Utilizing a series of fac-Re(CO)3 core based quinonoid containing complexes for photophysical and cell imaging studies

  摘要：

  A series of N boolean AND O bis-chelating bridging quinone ligands (H2L1, H2L2 and H2L3) have been utilized to synthesize four dinuclear fac-Re(CO)(3) based neutral complexes (1-4) by their reaction with Re(CO)(5)(OTf), where the N-donors 4-dimethylaminopyridine (for 1), 3,5-dibromopyridine (for 2) and acetonitrile (for 3 and 4) act as ancillary ligands. The complexes were characterized by FTIR, H-1 NMR, ESI-MS and elemental analysis. The structures of complexes 1-3 were analysed by X-ray diffraction methods. Photophysical investigations revealed that all the complexes display strong visible-light absorption with absorption maxima at around 500 nm (epsilon = 40000-50000 M-1 cm(-1)), whereas in the solid state the complexes display high intensity broad bands in the entire UV-Vis-NIR region. Complexes 1-4 were found to be luminescent in fluid solutions at room temperature. Favorable photophysical properties allowed their utilization as luminescent probes for live-cell imaging using HeLa cells, where complexes 2 and 4 were found to display good cellular uptake with co-localization in lysosomal compartments, which was observed as yellow fluorescence. Complexes 2 and 4 displayed very low cytotoxicity, as suggested by LDH production experiments. The photophysical properties, uptake pathway, localization properties and cytotoxicity of the complexes are discussed in detail. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.06.030
• 作为产物：
  描述：

  2,5-二氨基-2,5-环己二烯-1,4-二酮 、 2,4,6-三甲基苯胺 在 溶剂黄146 作用下， 生成 2,5-di-[2′,4′,6′-(tri-methyl)-anilino]-1,4-benzoquinone
  参考文献：
  名称：

  具有核醌桥的双核RuII配合物：通过明智的桥设计可调节氧化还原可转换NIR染料的电化学和光谱性质。

  摘要：

  桥接醌类配体是产生基于金属的可切换光电和磁性材料的重要平台。影响上述材料性能的一种可行方法是修改直接的金属-配体界面。我们在此介绍了一系列双核Ru II配合物，其中在桥接醌类配体上的供体原子组范围从[O，O，O，O]，[O，O，O，N]，[O，N，O， N]和[O，N，O，N']。另外，N-供体上的取代基也有所变化（共比较了八个不同的醌型桥）。为了比较目的，我们还提出了单核Ru II配合物。双核络合物充当可转换的NIR染料，在其混合价Ru II / Ru III中的NIR区域吸收。形式，但不在邻近的Ru II / Ru II和Ru III / Ru III州中。所述开关的电势（在该NIR吸收出现的电位）和λ最大NIR频带可以通过改变供体原子以及供电子性的取代基的氮原子上（调谐e。通过能力微调CA 。 0.4 V和λ最大通过约450 nm）。在桥的氮原子处引入更多的富电子取代基会导致更高的能

  DOI：

  10.1039/d0dt01351j

文献信息

• Tuning the Electronic Properties in Ruthenium-Quinone Complexes through Metal Coordination and Substitution at the Bridge
  作者：Hari Sankar Das、David Schweinfurth、Jan Fiedler、Marat M. Khusniyarov、Shaikh. M. Mobin、Biprajit Sarkar

  DOI：10.1002/chem.201204379

  日期：2014.4.7

  forms of all complexes. A combination of structural data, electrochemistry, UV/Vis/NIR/EPR spectroelectrochemistry, and DFT calculations is used to elucidate the electronic structures of the complexes. Our DFT results indicate that the electronic natures of the various redox states of the complexes in vacuum differ greatly from those in a solvent continuum. We show here the tuning possibilities that arise

  单核络合物[（bpy）2 Ru（L 1 -H）]（ClO 4），1（ClO 4）和双核络合物[（bpy）2 Ru（μ- L 1 -2H）Ru（bpy ）2 ]（CLO 4）2，2（CLO 4）2，[（联吡啶）2的Ru（μ -L 2 -2H）的Ru（联吡啶）2 ]（CLO 4）2，3（CLO 4）2，和[（bpy）2的Ru（μ -L 3 -2H）的Ru（联吡啶）2 ]（CLO 4）2，4（CLO 4）2（BPY = 2,2'-联吡啶，L 1 = 2,5-二- （异丙基氨基）-1,4-苯醌，L 2 = 2,5-二-（苄基氨基）-1,4-苯醌，L 3 = 2,5-二-[2,4,6-（三甲基）报道了具有对称取代的对苯醌配体L的[苯胺基] -1,4-苯醌）。在单-和双核配合物显示的键的定位，并通过苯酚型的“O结合到金属中心的两个潜在的桥连配体内键的长度分析-”和亚胺/亚胺中性“ N”供体。对于单核络合物1（ClO
• Multiple phenyl ring appended Re-based complexes for strong visible light absorption and DNA binding
  作者：Bholey Singh、Balaram Pani、Deepak Gupta

  DOI：10.1039/d1dt02216d

  日期：——

  phenyl rings. All the complexes displayed strong absorption (ε = 14 000–40 000 M−1 cm−1) over wide visible region (400–600 nm). Due to the interesting structural and photophysical properties of the complexes, a satisfactory DNA binding ability was observed. The binding of the complexes with DNA grooves was confirmed by a significant increase in the absorption intensities of the complexes in the visible region

  合成并表征了一系列具有 N∩O 双螯合配体和三苯基膦氧化物供体的面状-Re(CO) 3基无环配合物 ( 1–3 )。这些配合物最有趣的结构特征是两个配位配体均通过外部苯环进行功能化。单晶 X 射线衍射分析证实，每个分子都通过外部苯环表现出多种分子间超分子相互作用。所有配合物在宽可见光区域（400–600 nm）均表现出强吸收（ ε = 14 000–40 000 M -1 cm -1 ）。由于复合物有趣的结构和光物理特性，观察到了令人满意的 DNA 结合能力。通过复合物在可见光区域的吸收强度的显着增加、DNA的吸收增强和圆二色性证实了复合物与DNA凹槽的结合。
• Utilizing a series of fac-Re(CO)3 core based quinonoid containing complexes for photophysical and cell imaging studies
  作者：Deepak Gupta、Vikash Singh、Stephan Hohloch、Malaichamy Sathiyendiran、Karsten Tedin、Biprajit Sarkar

  DOI：10.1016/j.poly.2015.06.030

  日期：2015.11

  A series of N boolean AND O bis-chelating bridging quinone ligands (H2L1, H2L2 and H2L3) have been utilized to synthesize four dinuclear fac-Re(CO)(3) based neutral complexes (1-4) by their reaction with Re(CO)(5)(OTf), where the N-donors 4-dimethylaminopyridine (for 1), 3,5-dibromopyridine (for 2) and acetonitrile (for 3 and 4) act as ancillary ligands. The complexes were characterized by FTIR, H-1 NMR, ESI-MS and elemental analysis. The structures of complexes 1-3 were analysed by X-ray diffraction methods. Photophysical investigations revealed that all the complexes display strong visible-light absorption with absorption maxima at around 500 nm (epsilon = 40000-50000 M-1 cm(-1)), whereas in the solid state the complexes display high intensity broad bands in the entire UV-Vis-NIR region. Complexes 1-4 were found to be luminescent in fluid solutions at room temperature. Favorable photophysical properties allowed their utilization as luminescent probes for live-cell imaging using HeLa cells, where complexes 2 and 4 were found to display good cellular uptake with co-localization in lysosomal compartments, which was observed as yellow fluorescence. Complexes 2 and 4 displayed very low cytotoxicity, as suggested by LDH production experiments. The photophysical properties, uptake pathway, localization properties and cytotoxicity of the complexes are discussed in detail. (C) 2015 Elsevier Ltd. All rights reserved.
• Dinuclear Ru^IIcomplexes with quinonoid bridges: tuning the electrochemical and spectroscopic properties of redox-switchable NIR dyes through judicious bridge design
  作者：Shubhadeep Chandra、Fritz Weisser、Sinja Klenk、Julia Beerhues、David Schweinfurth、Biprajit Sarkar

  DOI：10.1039/d0dt01351j

  日期：——

  Bridging quinonoid ligands are important platforms for generating metal-based switchable optoelectronic and magnetic materials. A possible sound way of influencing the properties of the aforementioned materials is to modify the direct metal–ligand interface. We present herein a series of dinuclear RuII complexes where the set of donor atoms at the bridging quinonoid ligands range from [O,O,O,O], [O

  桥接醌类配体是产生基于金属的可切换光电和磁性材料的重要平台。影响上述材料性能的一种可行方法是修改直接的金属-配体界面。我们在此介绍了一系列双核Ru II配合物，其中在桥接醌类配体上的供体原子组范围从[O，O，O，O]，[O，O，O，N]，[O，N，O， N]和[O，N，O，N']。另外，N-供体上的取代基也有所变化（共比较了八个不同的醌型桥）。为了比较目的，我们还提出了单核Ru II配合物。双核络合物充当可转换的NIR染料，在其混合价Ru II / Ru III中的NIR区域吸收。形式，但不在邻近的Ru II / Ru II和Ru III / Ru III州中。所述开关的电势（在该NIR吸收出现的电位）和λ最大NIR频带可以通过改变供体原子以及供电子性的取代基的氮原子上（调谐e。通过能力微调CA 。 0.4 V和λ最大通过约450 nm）。在桥的氮原子处引入更多的富电子取代基会导致更高的能