TQA | 1355450-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: TQA
• 英文别名: tris(1-isoquinolylmethyl)amine；1-isoTQA；1-isoquinolin-1-yl-N,N-bis(isoquinolin-1-ylmethyl)methanamine
• CAS: 1355450-12-2
• 化学式: C₃₀H₂₄N₄
• 分子量: 440.547
• InChiKey: CLGMIYHSBYONRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 TQA 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [Zn(tris(1-isoquinolylmethyl)amine)(water)](perchlorate)2*0.5water
  参考文献：
  名称：

  Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)

  摘要：

  Isoquinoline-based tetradentate ligands with C-3-symmetry, tris(1- or 3-isoquinolylmethyl)amine (1- or 3-isoTQA), have been prepared and their zinc-induced fluorescence enhancement was investigated. Upon excitation at 324 nm, 1-isoTQA shows very weak fluorescence (phi = similar to 0.003) in DMF/H2O (1/1) solution. In the presence of zinc ion, 1-isoTQA exhibits fluorescence increase (phi = 0.041) at 359 and 470 nm. This fluorescence enhancement at 470 nm is specific for zinc. However, 3-isoTQA exhibited a smaller fluorescence enhancement upon zinc complexation (phi = 0.017, lambda(em) = 360 and 464 run) compared with 1-isoTQA. Crystal structures of zinc complexes of isoTQAs demonstrate the diminished steric crowding and shorter Zn-N-aromatic distances compared with isoTQENs (N,N,N,N'-tetrakis(isoquinolylmethyl)ethylenediamines) leads to a higher fluorescent response toward zinc relative to cadmium.

  DOI：

  10.1021/ic202159v
• 作为产物：
  描述：

  N-(1-isoquinolylmethyl)phthalimide 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 97.5h， 生成 TQA
  参考文献：
  名称：

  Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)

  摘要：

  Isoquinoline-based tetradentate ligands with C-3-symmetry, tris(1- or 3-isoquinolylmethyl)amine (1- or 3-isoTQA), have been prepared and their zinc-induced fluorescence enhancement was investigated. Upon excitation at 324 nm, 1-isoTQA shows very weak fluorescence (phi = similar to 0.003) in DMF/H2O (1/1) solution. In the presence of zinc ion, 1-isoTQA exhibits fluorescence increase (phi = 0.041) at 359 and 470 nm. This fluorescence enhancement at 470 nm is specific for zinc. However, 3-isoTQA exhibited a smaller fluorescence enhancement upon zinc complexation (phi = 0.017, lambda(em) = 360 and 464 run) compared with 1-isoTQA. Crystal structures of zinc complexes of isoTQAs demonstrate the diminished steric crowding and shorter Zn-N-aromatic distances compared with isoTQENs (N,N,N,N'-tetrakis(isoquinolylmethyl)ethylenediamines) leads to a higher fluorescent response toward zinc relative to cadmium.

  DOI：

  10.1021/ic202159v

文献信息

• Solid-Phase Synthesis as a Platform for the Discovery of New Ruthenium Complexes for Efficient Release of Photocaged Ligands with Visible Light
  作者：Rajgopal Sharma、Jessica D. Knoll、Nicholas Ancona、Phillip D. Martin、Claudia Turro、Jeremy J. Kodanko

  DOI：10.1021/ic502791y

  日期：2015.2.16

  great potential as therapeutics. A method was developed to rapidly synthesize, screen, and identify ruthenium-based caging groups that release nitriles upon irradiation with visible light. A diverse library of tetra- and pentadentate ligands was synthesized on polystyrene resin. Ruthenium complexes of the general formula [Ru(L)(MeCN)n]m+ (n = 1–3, m = 1–2) were generated from these ligands on solid phase

  钌基光笼基团作为生物工具具有重要的应用，并显示出巨大的治疗潜力。开发了一种快速合成，筛选和鉴定基于钌的笼形基团的方法，该基团会在可见光照射下释放出腈。在聚苯乙烯树脂上合成了多样化的四齿和五齿配体库。通式[Ru（L）（MeCN）n ] m +（n = 1-3，m的钌配合物= 1-2）是从固相上的这些配体生成的，然后从树脂上裂解下来进行光化学分析。数据表明光谱调谐和与可见光的反应性范围很广。通过溶液相合成了在可见光范围内显示出强吸收性的三种配合物用于比较。溶液和固相复合物的光化学行为非常吻合，这证实了文库方法可用于在短期内鉴定具有所需光反应性的候选物，从而避免了耗时的色谱法和化合物纯化。
• Isoquinoline-derivatized tris(2-pyridylmethyl)amines as fluorescent zinc sensors with strict Zn2+/Cd2+ selectivity
  作者：Yuji Mikata、Keiko Kawata、Saaya Takeuchi、Kaori Nakanishi、Hideo Konno、Saori Itami、Keiko Yasuda、Satoshi Tamotsu、Shawn C. Burdette

  DOI：10.1039/c4dt01054j

  日期：——

  Tris(2-pyridylmethyl)amine-based fluorescent ligands, N,N-bis(1-isoquinolylmethyl)-2-pyridylmethylamine (1-isoBQPA) and N,N-bis(7-methoxy-1-isoquinolylmethyl)-2-pyridylmethylamine (7-MeO-1-isoBQPA), have been prepared and the Zn2+-induced fluorescence enhancement has been investigated. Upon excitation at 324 nm, 1-isoBQPA exhibits a very weak emission (ϕ = ∼0.010) in DMF–H2O (1 : 1). Upon Zn2+ addition, the 1-isoBQPA fluorescence increases (ϕZn = 0.055) at 357 nm and 464 nm. The fluorescence enhancement at longer wavelengths is Zn2+-specific, whereas Cd2+ induces a small emission increase at 464 nm (ICd/I0 = 1.1, ICd/IZn = 14%). The Zn2+/Cd2+ selectivity of the fluorescent response correlates with the Cd–Nisoquinoline and Zn–Nisoquinoline bond distances measured in the crystal structures. Introduction of methoxy groups into the 1-isoBQPA chromophore enhances the fluorescence significantly (ϕZn = 0.213), which affords 7-MeO-1-isoBQPA properties amenable for fluorescence microscopy in living cells.

  三(2-吡啶基甲基)胺基荧光配体、N,N-双(1-异喹啉基甲基)-2-吡啶基甲胺(1-isoBQPA)和N,N-双(7-甲氧基-1-异喹啉基甲基)-2-吡啶基甲胺(7-MeO-1-isoBQPA)，已制备并研究了 Zn2+ 诱导的荧光增强。在 324 nm 激发下，1-isoBQPA 在 DMF–H2O (1 : 1) 中表现出非常弱的发射 (phi = ∼0.010)。添加 Zn2+ 后，1-isoBQPA 荧光在 357 nm 和 464 nm 处增强 (ψZn = 0.055)。较长波长处的荧光增强是 Zn2+ 特异性的，而 Cd2+ 会在 464 nm 处引起小幅发射增加（ICd/I0 = 1.1，ICd/IZn = 14%）。荧光响应的 Zn2+/Cd2+ 选择性与晶体结构中测量的 Cd-Nisoquinoline 和 Zn-Nisoquinoline 键距相关。将甲氧基引入 1-isoBQPA 发色团可显着增强荧光 (ψZn = 0.213)，从而提供适合活细胞荧光显微镜观察的 7-MeO-1-isoBQPA 特性。
• Structure and electrochemical properties of (μ-O)₂Mn₂(<scp>iii</scp>,<scp>iii</scp>) and (μ-O)₂Mn₂(<scp>iii</scp>,<scp>iv</scp>) complexes supported by pyridine-, quinoline-, isoquinoline- and quinoxaline-based tetranitrogen ligands
  作者：Yuji Mikata、Yasuko Kuroda、Kyoko Naito、Kana Murakami、Chihiro Yamamoto、Shoko Yabe、Shizuka Yonemura、Arimasa Matsumoto、Hajime Katano

  DOI：10.1039/d1dt00184a

  日期：——

  stabilize the Mn2(III,III) oxidation state, whereas, isoquinoline ligands afford Mn2(III,IV) complexes. A systematic comparison of the differences in structural parameters and redox potentials of a total of 14 complexes with a (μ-O)2Mn2 diamond core, which includes corresponding pyridine and quinoxaline derivatives as supporting ligands, highlights the distinct deviation of quinoline and tripodal amine

  使用基于喹啉和异喹啉的四胺配体制备了七个具有Mn 2（III，III）或Mn 2（III，IV）氧化态的双（μ-氧代）二锰配合物。配体的结构包括带有两个或三个含氮杂芳族化合物的乙二胺，反式-1，2-环己二胺和三脚架胺。不论配体中的脂肪族氮原子的骨架和数量如何，喹啉络合物都能稳定Mn 2（III，III）的氧化态，而异喹啉配体可提供Mn 2（III，IV））复合体。系统地比较了总共14种具有（μ-O）2 Mn 2金刚石核的配合物的结构参数和氧化还原电位的差异，其中包括相应的吡啶和喹喔啉衍生物作为支持配体，突出了喹啉和三脚架的明显偏差该配体系列中的胺基序。
• Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)
  作者：Yuji Mikata、Keiko Kawata、Satoshi Iwatsuki、Hideo Konno

  DOI：10.1021/ic202159v

  日期：2012.2.6

  Isoquinoline-based tetradentate ligands with C-3-symmetry, tris(1- or 3-isoquinolylmethyl)amine (1- or 3-isoTQA), have been prepared and their zinc-induced fluorescence enhancement was investigated. Upon excitation at 324 nm, 1-isoTQA shows very weak fluorescence (phi = similar to 0.003) in DMF/H2O (1/1) solution. In the presence of zinc ion, 1-isoTQA exhibits fluorescence increase (phi = 0.041) at 359 and 470 nm. This fluorescence enhancement at 470 nm is specific for zinc. However, 3-isoTQA exhibited a smaller fluorescence enhancement upon zinc complexation (phi = 0.017, lambda(em) = 360 and 464 run) compared with 1-isoTQA. Crystal structures of zinc complexes of isoTQAs demonstrate the diminished steric crowding and shorter Zn-N-aromatic distances compared with isoTQENs (N,N,N,N'-tetrakis(isoquinolylmethyl)ethylenediamines) leads to a higher fluorescent response toward zinc relative to cadmium.