2-(6-Aminohexyl)-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one | 1310827-21-4

• 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-(6-Aminohexyl)-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• 英文别名: 2-(6-aminohexyl)-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 1310827-21-4
• 化学式: C₃₄H₄₄N₄O₂
• 分子量: 540.749
• InChiKey: DYNFJJPOKFQWQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6-Aminohexyl)-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one 在 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Switching of the Triplet Excited State of Rhodamine/Naphthaleneimide Dyads: An Experimental and Theoretical Study

  摘要：

  Rhodamine-bromonaphthaleneimide (RB-NI) and rhodamine-bromonaphthalenediimide (RB-NDI) dyads were prepared for switching of the triplet excited states. Bromo-NI or bromo-NDI parts in the dyads are the spin converters, i.e., the triplet state producing modules, whereas the RB unit is the acid-activatable electron donor/energy acceptor. NI and NDI absorb at 359 and 541 nm, and the T1 state energy levels are 2.25 and 1.64 eV, respectively. RB undertakes the reversible spirolactam (RB-c) <-> opened amide (RB-o) transformation. RB-c shows no visible light absorption, and the triplet-state energy level is E-T1 = 3.36 eV. Conversely RB-o shows strong absorption at 557 nm, and E-T1 is 1.73 eV. Thus, the acid-activated fluorescence-resonance-energy-transfer (FRET) competes with the ISC of NI or NDI. No triplet state was observed for the dyads with nanosecond time-resolved transient absorption spectroscopy. Upon addition of acid, strong fluorescence and long-living triplet excited states were observed. Thus, the producing of triplet state is acid-activatable. The triplet state of RB-NI is localized on RB-o part, whereas in RB-NDI the triplet state is delocalized on both the NDI and RB-o units. The ISC of spin converter was not outcompeted by RET. These studies are useful for switching of triplet excited state.

  DOI：

  10.1021/jo502554y
• 作为产物：
  描述：

  1,6-己二胺 、 罗丹明B 以 乙醇 为溶剂， 生成 2-(6-Aminohexyl)-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
  参考文献：
  名称：

  具有若丹明单元的Ru（联吡啶）3 [PF6] 2配合物-合成，光物理性质及其在酸可控三重-三重An灭上转换中的应用

  摘要：

  制备了钌（II）三（联吡啶）-若丹明三联体以控制外部刺激（酸）的三重态状态。罗丹明部分是一种酸响应模块，Ru II配位中心负责在光激发下形成三重态。通过稳态UV / Vis吸收和发光光谱，电化学表征和纳秒/飞秒瞬态吸收光谱，我们发现，成对层赋予淬火三重态的金属-配体电荷转移（3 MLCT）激发态（寿命τ Ť = 103.6纳秒与τ Ť由于存在光致电子转移（PET）过程，因此在不存在酸的条件下= = 1.58 µs）。在存在酸的情况下，若丹明单元可逆地从螺内酰胺结构转变为开酰胺结构。因此，PET受到抑制，三重态寿命（5.70 µs）延长，T 1状态重新定位于若丹明单元。这是首次同时控制Ru II配合物的基本三重态激发态性质，即三重态寿命和局部化。分子内单重态-三重态能量传递和三重态-三重态能量传递（TTET，3 MLCT→ 3在飞秒和纳秒瞬态吸收光谱中分别观察到三元组的IL）。该二分体用于酸可控的三重态-三重态an灭上转换。

  DOI：

  10.1002/ejic.201600755

文献信息

• Three colorimetric and off-on fluorescent chemosensors for Fe³⁺in aqueous media
  作者：Meimei Chai、Man Li、Di Zhang、Cui-cui Wang、Yong Ye、Yufen Zhao

  DOI：10.1002/bio.2493

  日期：2013.7

  Three Rhodamine B derivatives were synthesized and characterized by ESI-MS, NMR, HR-MS and IR. The probes exhibit high selectivity and sensitivity towards Fe3+ over other metal ions in CH3CN–water. Upon the addition of Fe3+, the spirocyclic ring of the probe was opened and a significant enhancement of visible color and fluorescence within the range of 540–700 nm was observed. The colorimetric and fluorescent response to Fe3+ can be conveniently detected even by the naked eye, which provides a facile method for the visual detection of Fe3+. Job's plot, fluorescence titration and MS indicated the formation of 1:2 complexes between the probes and Fe3+. The reversibility of the reaction establishes the potential of these probes as chemosensors for Fe3+ detection. Copyright © 2013 John Wiley & Sons, Ltd.

  我们合成了三种罗丹明 B 衍生物，并通过 ESI-MS、NMR、HR-MS 和 IR 对其进行了表征。在 CH3CN-水中，这些探针对 Fe3+（而非其他金属离子）具有高选择性和高灵敏度。加入 Fe3+ 后，探针的螺环被打开，可见光颜色和荧光在 540-700 纳米范围内显著增强。对 Fe3+ 的比色和荧光反应甚至可以用肉眼方便地检测到，这为目视检测 Fe3+ 提供了一种简便的方法。约伯图、荧光滴定和质谱均表明探针与 Fe3+ 形成了 1:2 的复合物。反应的可逆性证明了这些探针作为化学传感器检测 Fe3+ 的潜力。Copyright © 2013 John Wiley & Sons, Ltd. All Rights Reserved.
• Switching of the Triplet Excited State of Rhodamine/Naphthaleneimide Dyads: An Experimental and Theoretical Study
  作者：Xiaoneng Cui、Jianzhang Zhao、Zhangrong Lou、Shujing Li、Huijian Wu、Ke-li Han

  DOI：10.1021/jo502554y

  日期：2015.1.2

  Rhodamine-bromonaphthaleneimide (RB-NI) and rhodamine-bromonaphthalenediimide (RB-NDI) dyads were prepared for switching of the triplet excited states. Bromo-NI or bromo-NDI parts in the dyads are the spin converters, i.e., the triplet state producing modules, whereas the RB unit is the acid-activatable electron donor/energy acceptor. NI and NDI absorb at 359 and 541 nm, and the T1 state energy levels are 2.25 and 1.64 eV, respectively. RB undertakes the reversible spirolactam (RB-c) <-> opened amide (RB-o) transformation. RB-c shows no visible light absorption, and the triplet-state energy level is E-T1 = 3.36 eV. Conversely RB-o shows strong absorption at 557 nm, and E-T1 is 1.73 eV. Thus, the acid-activated fluorescence-resonance-energy-transfer (FRET) competes with the ISC of NI or NDI. No triplet state was observed for the dyads with nanosecond time-resolved transient absorption spectroscopy. Upon addition of acid, strong fluorescence and long-living triplet excited states were observed. Thus, the producing of triplet state is acid-activatable. The triplet state of RB-NI is localized on RB-o part, whereas in RB-NDI the triplet state is delocalized on both the NDI and RB-o units. The ISC of spin converter was not outcompeted by RET. These studies are useful for switching of triplet excited state.
• A Ru(bipyridine) ₃ [PF ₆ ] ₂ Complex with a Rhodamine Unit – Synthesis, Photophysical Properties, and Application in Acid‐Controllable Triplet–Triplet Annihilation Upconversion
  作者：Xiaoneng Cui、Jianzhang Zhao、Ahmet Karatay、Halime Gul Yaglioglu、Mustafa Hayvali、Betül Küçüköz

  DOI：10.1002/ejic.201600755

  日期：2016.11

  nanosecond/femtosecond transient absorption spectroscopy, we found that the dyad gives a quenched triplet metal‐to‐ligand charge‐transfer (3MLCT) excited state (lifetime τT = 103.6 ns vs. τT = 1.58 µs) in the absence of acid, owing to a photoinduced electron transfer (PET) process. In the presence of acid, the rhodamine unit transforms reversibly from the spirolactam structure into the open‐amide structure; thus

  制备了钌（II）三（联吡啶）-若丹明三联体以控制外部刺激（酸）的三重态状态。罗丹明部分是一种酸响应模块，Ru II配位中心负责在光激发下形成三重态。通过稳态UV / Vis吸收和发光光谱，电化学表征和纳秒/飞秒瞬态吸收光谱，我们发现，成对层赋予淬火三重态的金属-配体电荷转移（3 MLCT）激发态（寿命τ Ť = 103.6纳秒与τ Ť由于存在光致电子转移（PET）过程，因此在不存在酸的条件下= = 1.58 µs）。在存在酸的情况下，若丹明单元可逆地从螺内酰胺结构转变为开酰胺结构。因此，PET受到抑制，三重态寿命（5.70 µs）延长，T 1状态重新定位于若丹明单元。这是首次同时控制Ru II配合物的基本三重态激发态性质，即三重态寿命和局部化。分子内单重态-三重态能量传递和三重态-三重态能量传递（TTET，3 MLCT→ 3在飞秒和纳秒瞬态吸收光谱中分别观察到三元组的IL）。该二分体用于酸可控的三重态-三重态an灭上转换。