2-amino-3',6'-bis(ethylamino)-2',7'-dimethylspiro[isoindoline-1,9'-xanthene]-3-thione | 1305196-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-amino-3',6'-bis(ethylamino)-2',7'-dimethylspiro[isoindoline-1,9'-xanthene]-3-thione
• 英文别名: 2-amino-3',6'-bis(ethylamino)-2',7'-dimethylspiro[isoindoline-1,9'-xanthen]-3-thione
• CAS: 1305196-59-1
• 化学式: C₂₆H₂₈N₄OS
• 分子量: 444.601
• InChiKey: LEOSCZSCJZQKRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.55
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-amino-3',6'-bis(ethylamino)-2',7'-dimethylspiro[isoindoline-1,9'-xanthene]-3-thione 以 aq. phosphate buffer 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  硫调节的Hg 2+高灵敏度荧光探针的合成与应用

  摘要：

  摘要罗丹明基荧光探针因具有出色的光学性能而被广泛应用于化学分析，环境分析和生命科学领域。基于Hg 2+的亲硫特性，我们的研究小组以C = S结构基序为核心片段，设计并合成了三种具有不同取代基的肉桂醛的新型探针，这些探针具有很高的选择性和出色的灵敏度。研究了这些探针的结构-性质关系，即由吸电子效应和重原子效应引起的光学变化。此外，这些Hg 2+探针可用于活体小鼠成像，这为活体有机体中的汞（II）离子定量成像提供了有希望的工具。

  DOI：

  10.1016/j.cclet.2017.09.027
• 作为产物：
  描述：

  rhodamine 6G 在 劳森试剂 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 2-amino-3',6'-bis(ethylamino)-2',7'-dimethylspiro[isoindoline-1,9'-xanthene]-3-thione
  参考文献：
  名称：

  硫调节的Hg 2+高灵敏度荧光探针的合成与应用

  摘要：

  摘要罗丹明基荧光探针因具有出色的光学性能而被广泛应用于化学分析，环境分析和生命科学领域。基于Hg 2+的亲硫特性，我们的研究小组以C = S结构基序为核心片段，设计并合成了三种具有不同取代基的肉桂醛的新型探针，这些探针具有很高的选择性和出色的灵敏度。研究了这些探针的结构-性质关系，即由吸电子效应和重原子效应引起的光学变化。此外，这些Hg 2+探针可用于活体小鼠成像，这为活体有机体中的汞（II）离子定量成像提供了有希望的工具。

  DOI：

  10.1016/j.cclet.2017.09.027

文献信息

• Rhodamine-based highly sensitive colorimetric off-on fluorescent chemosensor for Hg2+ in aqueous solution and for live cell imaging
  作者：Hengguo Wang、Yapeng Li、Shufei Xu、Yanchun Li、Chen Zhou、Xiaoliang Fei、Lei Sun、Chaoqun Zhang、Yaoxian Li、Qingbiao Yang、Xiaoyi Xu

  DOI：10.1039/c0ob01032d

  日期：——

  A novel rhodamine-based highly sensitive and selective colorimetric off-on fluorescent chemosensor for Hg2+ ions is designed and prepared by using the well-known thiospirolactam rhodamine chromophore and furfural hydrazone as signal-reporting groups. The photophysical characterization and Hg2+-binding properties of sensor RS1 in neutral N, N-dimethylformamide (DMF) aqueous solution are also investigated. The signal change of the chemosensor is based on a specific metal ion induced reversible ring-opening mechanism of the rhodamine spirolactam. The response of the chemosensor for Hg2+ ions is instantaneous and reversible. And it successfully exhibits a remarkably “turn on” response toward Hg2+ over other metal ions (even those that exist in high concentration). Moreover, this sensor is applied for in vivo imaging in Rat Schwann cells to confirm that RS1 can be used as a fluorescent probe for monitoring Hg2+ in living cells with satisfying results, which further demonstrates its value of practical applications in environmental and biological systems.

  利用众所周知的硫代螺内酰胺罗丹明发色团和糠醛腙作为信号报告基团，设计并制备了一种新型基于罗丹明的高灵敏度、选择性比色关闭开启荧光化学传感器，用于 Hg2+ 离子。还研究了传感器 RS1 在中性 N,N-二甲基甲酰胺 (DMF) 水溶液中的光物理表征和 Hg2+ 结合特性。化学传感器的信号变化基于特定金属离子诱导的罗丹明螺内酰胺的可逆开环机制。化学传感器对 Hg2+ 离子的响应是瞬时且可逆的。与其他金属离子（甚至是高浓度存在的金属离子）相比，它成功地对 Hg2+ 表现出显着的“开启”响应。此外，将该传感器应用于大鼠雪旺细胞体内成像，证实RS1可以作为活细胞中Hg2+的荧光探针进行监测，并取得了满意的结果，进一步证明了其在环境和生物系统中的实际应用价值。
• Multiple fluorescent sensing responses of a 2D framework structure towards explosive: Synthesis, characterization and sensing performance
  作者：Ze Zhao、Liang Liu

  DOI：10.1016/j.molstruc.2021.130418

  日期：2021.8

  colorimetric sensing behavior. Its rhodamine emission component was enhanced obviously by PA as well, but its Eu emission component was slightly quenched by PA, showing ratiometric fluorescent sensing response towards PA. Linear sensing response towards PA was found for both sensing channels with LOD as low as 4.8 μM. RS@EuBTC depicted good selectivity towards PA over interferents. Its sensing mechanism

  在以下工作中，我们报告了一个光学传感器平台，该平台具有用于苦味酸（PA）的双传感通道，名为RS @ EuBTC。该传感平台由发光稀土MOF衍生的支持基质和罗丹明衍生的传感探针组成。通过XRD，IR，TGA，吸收，发射和激发光谱，确定了RS @ EuBTC的复合结构。它的若丹明吸收成分通过增加可见光区的PA浓度而增强，表现出比色传感行为。PA还可明显增强其若丹明发射成分，但PA可使Eu发射成分略有淬灭，显示出对PA的比例荧光传感响应。在LOD低至4.8μM的两个感应通道中都发现了对PA的线性感应响应。RS @ EuBTC表现出对PA相对于干扰物具有良好的选择性。PA的质子引发的若丹明发射开启效应与PA的电子拉动效应引发的电子转移过程引起的Eu发射关闭效应相结合，使其感应机制得到了肯定。RS @ EuBTC的新颖之处在于其肉眼检测和具有良好选择性的双感应通道的可能性。
• [5]Helicene-rhodamine 6 G hybrid-based sensor for ultrasensitive Hg2+ detection and its biological applications
  作者：Anuwut Petdum、Natchawat Faichu、Jitnapa Sirirak、Praetip Khammultri、Vinich Promarak、Waraporn Panchan、Thanasat Sooksimuang、Adisri Charoenpanich、Nantanit Wanichacheva

  DOI：10.1016/j.jphotochem.2020.112473

  日期：2020.5

  A novel chromogenic and fluorometric sensor based on [5]helicene-like-dye-bearing rhodamine 6 G thiohydrazide, i.e. NF09, was successfully designed and synthesized for the detection of Hg2+. NF09 exhibited ultrasensitive and highly selective recognition of Hg2+ on the basis of the fluorescence resonance energy transfer process from the [5]helicene-like donor to the rhodamine 6 G acceptor. The photophysical

  基于新型显色和荧光传感器[5]螺烯样染料轴承罗丹明6G的硫代酰肼，即NF09，成功地设计并用于检测汞的合成2+。NF09在从[5]螺旋状供体到若丹明6 G受体的荧光共振能量转移过程的基础上，对Hg 2+表现出超敏和高度选择性的识别。传感器的光物理特性说明了187 nm的非常大的伪斯托克斯位移。NF09可以有效测定痕量的Hg 2+，检测限低至0.3 ppb（1.5 nM），低于最大的Hg 2+美国环境保护局指定的饮用水中的浓度。基于发色变化特性，NF09可以通过肉眼检测真实样品（例如亮肤霜，贻贝，金枪鱼片和鲑鱼片）中的Hg 2+含量。另外，该传感器通过荧光成像显示出对人细胞和植物根组织中Hg 2+的有效检测。传感器的连续检测和有效响应可确保将其用于Hg 2+污染暴发的实时监视和控制。
• Silver nanoparticle incorporated colorimetric/fluorescence sensor for sub-ppb detection of mercury ion via plasmon-enhanced fluorescence strategy
  作者：Nirawit Kaewnok、Sasiwimon Kraithong、Thitiwat Mahaveero、Phornphimon Maitarad、Jitnapa Sirirak、Nantanit Wanichacheva、Pattanawit Swanglap

  DOI：10.1016/j.jphotochem.2022.114140

  日期：2022.12

  Mercury released by industrial processes is a global pollution that threatens human health and the environment. In this study, a colorimetric and fluorescence sensor derived from rhodamine 6G thioamide (RS) was synthesized. The sensor displayed “turn on” fluorescence signaling with the detection limit of 0.49 ppb and the chromogenic change from colorless to pink upon selective sensing of mercury ion

  工业过程释放的汞是一种威胁人类健康和环境的全球性污染。在这项研究中，合成了一种源自罗丹明 6G 硫代酰胺 ( RS ) 的比色和荧光传感器。传感器显示“开启”荧光信号，检测限为 0.49 ppb，选择性感应汞离子 (Hg 2+ ) 后显色从无色变为粉红色。此外，通过将RS与合成的蓝色银纳米粒子 ( B-AgNPs ) 结合来利用等离子体增强以获得RS + B-AgNPs，通过非辐射能量转移导致更大的发射荧光量子产率，从而提高了传感器的灵敏度。与裸传感器的检测限相比，RS + B-AgNPs的检测限低约 16 倍 (0.030 ppb)。RS + B-AgNPs可用于监测真实样品中受污染的 Hg 2+，例如饮用水和海鲜鱼片。该结果表明传感器RS + B-AgNPs可以容忍来自真实样品基质的干扰。此外，由RS制成的试纸还显示了Hg 2+的定性和定量筛查，比色变化快，肉眼可以清楚地观察到。所有这些能力表明RS和RS
• Hg(II) sensing platforms with improved photostability: The combination of rhodamine derived chemosensors and up-conversion nanocrystals
  作者：Kai Song、Jingang Mo、Chengwen Lu

  DOI：10.1016/j.saa.2017.02.034

  日期：2017.5

  This paper reported two nanocomposite sensing platforms for Hg(II) detection with improved photostability, using two rhodamine derivatives as chemosensors and up-conversion nanocrystals as excitation host, respectively. There existed a secondary energy transfer from this excitation host to these chemosensors, which was confirmed by spectral analysis, energy transfer radius calculation and emission decay lifetime comparison. In this case, chemosensor photostability was greatly improved. Further analysis suggested that these chemosensors recognized Hg(II) following a simple binding stoichiometry of 1:1. Hg(II) sensing performance of these sensing platforms was analyzed through their emission spectra upon various Hg( II) concentrations. Emission spectral response, Stem-Volmer equation, emission stability and sensing selectivity were discussed in detail. It was finally concluded that these chemosensors showed emission turn on effect towards Hg(II), with high photostability, good selectivity and linear response. (C) 2017 Elsevier B.V. All rights reserved.