7-diethylamino-3-(4-formylphenyl)coumarin | 1318794-36-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-diethylamino-3-(4-formylphenyl)coumarin
• 英文别名: 4-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)benzaldehyde；4-[7-(Diethylamino)-2-oxochromen-3-yl]benzaldehyde；4-[7-(diethylamino)-2-oxochromen-3-yl]benzaldehyde
• CAS: 1318794-36-3
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: ZXLULBLFHKRPFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  538.4±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-diethylamino-3-(4-formylphenyl)coumarin 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.84h， 生成 meso-(4-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)phen-1-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  A series of dual-responsive Coumarin-Bodipy probes for local microviscosity monitoring

  摘要：

  Local microviscosity monitoring in living cells is a powerful tool to determine their healthy status in either a specific organelle or in the cytosol. Here is presented the rational design of a new family of self-calibrating dual-microviscosity probes as a strategy to improve the probe response at low viscosity ranges. We found one of the probes is useful to determine low viscosity variations in living cells where subtle stiffening of the rotor group in the probe can increase its viscosity sensitivity. Further X-ray structure analysis, fluorescence anisotropic measurements, and quantum chemical calculations of the electronic excitation by means of a natural transition orbital (NTO) analysis confirmed the observed response. The present work demonstrates that small viscosity variations (0.01-0.1 cP) in cells require improved analytical sensitivity to be properly monitored.

  DOI：

  10.1016/j.dyepig.2018.05.009
• 作为产物：
  描述：

  香豆素 110 在 四(三苯基膦)钯 、 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 7-diethylamino-3-(4-formylphenyl)coumarin
  参考文献：
  名称：

  钌（II）-聚亚胺-香豆素光捕获分子阵列：基于三重态-三重态Ann灭的上转换的设计原理和应用

  摘要：

  Ru II –双吡啶复合物通常在紫外光谱中吸收450 nm以下，并且其摩尔消光系数仅为中等（ε <16000  M -1  cm -1）。因此，具有强烈可见光吸收的Ru II-聚亚胺络合物引起了人们的极大兴趣。但是，没有有效的光捕获钌（II）/有机发色团阵列的报道。在此，我们报告了第一个可见光捕获Ru II-香豆素阵列，其在475 nm处吸收（ε高达63 300  M -1  cm -1，比典型的Ru II高4倍。–聚亚胺配合物）。这些阵列中的供体激发态可以有效地转化为受体激发态（即有效的能量转移），而不会损失受体的磷光量子产率。基于稳态和时间分辨光谱以及DFT计算，我们提出了设计Ru II-聚吡啶-发色团光捕获阵列的一般规则，该规则指出配体的1 IL能级必须接近于金属到配体电荷转移（M LCT）状态的各自能级。能量水平低于相应的1 M LCT / 3 M的1 IL / 3 ILLCT状态

  DOI：

  10.1002/chem.201101377

文献信息

• 一种次氯酸荧光探针及其制备方法和应用
  申请人：齐鲁工业大学

  公开号：CN109400563B

  公开（公告）日：2022-06-03

  一种次氯酸荧光探针及其制备方法和应用，该探针的分子式为：C26H24N4O6S；本发明设计的次氯酸荧光探针，合成步骤简单、原料易得、合成路线成熟，能够对细胞中的次氯酸进行快速准确检测并可以进行荧光成像研究。
• Ruthenium(II)–Polyimine–Coumarin Light‐Harvesting Molecular Arrays: Design Rationale and Application for Triplet–Triplet‐Annihilation‐Based Upconversion
  作者：Wanhua Wu、Shaomin Ji、Wenting Wu、Jingyin Shao、Huimin Guo、Tony D. James、Jianzhang Zhao

  DOI：10.1002/chem.201101377

  日期：2012.4.16

  calculations, we proposed a general rule for the design of RuII–polypyridine–chromophore light‐harvesting arrays, which states that the 1IL energy level of the ligand must be close to the respective energy level of the metal‐to‐ligand charge‐transfer (MLCT) states. Lower energy levels of 1IL/3IL than the corresponding 1MLCT/3MLCT states frustrate the cascade energy‐transfer process and, as a result, the harvested

  Ru II –双吡啶复合物通常在紫外光谱中吸收450 nm以下，并且其摩尔消光系数仅为中等（ε <16000  M -1  cm -1）。因此，具有强烈可见光吸收的Ru II-聚亚胺络合物引起了人们的极大兴趣。但是，没有有效的光捕获钌（II）/有机发色团阵列的报道。在此，我们报告了第一个可见光捕获Ru II-香豆素阵列，其在475 nm处吸收（ε高达63 300  M -1  cm -1，比典型的Ru II高4倍。–聚亚胺配合物）。这些阵列中的供体激发态可以有效地转化为受体激发态（即有效的能量转移），而不会损失受体的磷光量子产率。基于稳态和时间分辨光谱以及DFT计算，我们提出了设计Ru II-聚吡啶-发色团光捕获阵列的一般规则，该规则指出配体的1 IL能级必须接近于金属到配体电荷转移（M LCT）状态的各自能级。能量水平低于相应的1 M LCT / 3 M的1 IL / 3 ILLCT状态
• Visible‐Light Harvesting with Cyclometalated Iridium(III) Complexes Having Long‐Lived ³ IL Excited States and Their Application in Triplet–Triplet‐Annihilation Based Upconversion
  作者：Jifu Sun、Wanhua Wu、Huimin Guo、Jianzhang Zhao

  DOI：10.1002/ejic.201100501

  日期：2011.7

  (TTA) upconversion (upconversion quantum yields, ΦUC, are up to 23.4 %). We propose that weakly phosphorescent or even nonphosphorescent transition metal complexes can be used as triplet sensitizers for TTA upconversion, instead of the currently used phosphorescent complexes. Our design of the light-harvesting IrIII complexes will be helpful for the preparation of transition metal complexes with intense

  通过将捕光香豆素掺入二亚胺配体中，制备了在可见光区（ϵ = 70920 M–1 cm–1，466 nm 处）具有强吸收的环金属化铱 (III) 配合物（用于比较：ϵ = 7030 M–1 cm –1 对于没有光捕获能力的模型二亚胺复合物，在 371 nm 处）。该复合物具有长寿命的内配体三重激发态（3IL，由三重态的自旋密度分析支持）。在室温下，寿命 τT 高达 75.5 μs，由纳秒时间分辨瞬态吸收光谱确定。尽管观察到复合物的磷光较弱（ΦP = 0.6–0.7 %），但证明三重激发态（T1）在光激发时有效填充，通过在三重态-三重态湮灭 (TTA) 上转换中使用复合物作为三重态敏化剂（上转换量子产率，ΦUC，高达 23.4%）。我们建议弱磷光甚至非磷光过渡金属配合物可用作 TTA 上转换的三线态敏化剂，而不是目前使用的磷光配合物。我们设计的捕光 IrIII 配合物将有助于制备具有强烈吸收可
• Highly selective fluorescence turn-on probe for glutathione
  作者：Soo-Yeon Lim、Sanghee Lee、Seung Bum Park、Hae-Jo Kim

  DOI：10.1016/j.tetlet.2011.05.086

  日期：2011.7

  An activated coumarin-3-phenyl enone (1) by an intramolecular hydrogen bond has shown a selective and ratiometric response toward GSH and Cys over other natural amino acids through the Michael addition reaction of a thiol group to 1. When GSH was added to 1, a prominent color change together with a fluorescence turn-on property was observed so that submillimolar GSH was detectable. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and density functional theory study of novel coumarin-type dyes for dye sensitized solar cells
  作者：Liang Han、Huabiao Wu、Yanhong Cui、Xiaoyan Zu、Qing Ye、Jianrong Gao

  DOI：10.1016/j.jphotochem.2014.06.001

  日期：2014.9

  A series of novel coumarin-type dyes were synthesized with coumarin donor, pi bridges containing benzene and cyanoacetic acid or rhodanine acetic acid acceptor. The light-harvesting capabilities and photovoltaic performance of these dyes were investigated systematically. Moreover, density functional theory study of these coumarin dyes was performed. Among these compounds, dye with phenylthiophene bridge exhibits obvious superiority on optical and photovoltaic properties when compared with those of benzene or biphenyl bridge. Dyes bearing cyanoacetic acid acceptor have higher IPCE value and hence display better photovoltaic performance than those with rhodanine acetic acid acceptor. Dye with phenylthiophene bridge and cyanoacetic acid acceptor shows the most efficient photoelectricity conversion efficiency and has the maximum eta value of 3.62% (V-oc = 660 mV, J(sc) = 7.72 mA/cm(2), ff = 0.71) under simulated AM 1.5 irradiation (100 mW/cm(2)). (C) 2014 Elsevier B.V. All rights reserved.