7-(3,4-dicyanophenoxy)-4-methylcoumarin | 1051388-30-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(3,4-dicyanophenoxy)-4-methylcoumarin
• 英文别名: 4-(4-methyl-2-oxo-2H-chromen-7-yloxy)-phthalonitrile；4-Methyl-7-(3,4-dicyanophenoxy)coumarin；4-(4-methyl-2-oxochromen-7-yl)oxybenzene-1,2-dicarbonitrile
• CAS: 1051388-30-7
• 化学式: C₁₈H₁₀N₂O₃
• 分子量: 302.289
• InChiKey: IAOFYTHQODJJIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(3,4-dicyanophenoxy)-4-methylcoumarin 在 N,N-二甲基乙醇胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 24.0h， 以63%的产率得到
  参考文献：
  名称：

  带有香豆素衍生物的新型非金属和金属酞菁的便捷合成：合成、表征、聚集行为和抗菌活性

  摘要：

  无金属和在外围带有四个香豆素基团的金属酞菁 3-10 是通过新前体的环四聚反应制备的，即 4-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-phthalitrile 1 和 4- (2-Oxo-2H-chromen-7-yloxy)-phthalonitrile 2 在相应的二价金属盐（Zn (II)、Cu(II) 和 Co(II)）存在下。未金属化的 3 和金属酞菁的聚集行为5 进行了研究。新型邻苯二甲腈衍生物 1-2 是通过 4-硝基邻苯二甲腈与 7-羟基-4-甲基香豆素和 7-羟基香豆素在极性非质子溶剂（DMF 或 DMSO）中在干燥 K2CO3 为碱存在下反应合成的新产品的表征涉及多种方法的组合，包括元素分析、IR、UV-vis、1H NMR、13C NMR 和质谱。大多数新化合物 3-10 表现出重要的抗菌活性。

  DOI：

  10.1007/s10847-016-0655-7
• 作为产物：
  描述：

  羟甲香豆素 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63.7%的产率得到7-(3,4-dicyanophenoxy)-4-methylcoumarin
  参考文献：
  名称：

  具有轴向氯化物配体的新型7-羟基-4-甲基香豆素四取代金属酞菁的合成，光物理和热性质

  摘要：

  这项工作首次报道了带有轴向氯化物配体的7-羟基-4-甲基香豆素四取代的钌（III）（4a），铟（III）（4b），锡（IV）（4c）酞菁的合成。这些新的金属酞菁在许多有机溶剂中显示出良好的溶解性。这项研究还研究了化合物4a，4b和4c的光物理性质（荧光量子产率和寿命）。通过添加1,4-苯醌（BQ）可有效地猝灭这三种金属酞菁的荧光。热稳定性研究表明，4a和4b在300°C的温度下都是稳定的。

  DOI：

  10.1016/j.dyepig.2011.10.006

文献信息

• Synthesis and properties of carboxyl-substituted coumarin–phthalocyanine dyad dyes: effect of linker unit
  作者：Xuejun Zhang、Xilin Pei、Chaoqiang Liao、Li Zou

  DOI：10.1007/s11164-016-2792-4

  日期：2017.5

  Two novel coumarin-substituted phthalocyanine dyes (CAPc and CSPc) with different linking units, using carboxylic groups as electron acceptor and injector, were designed, synthesized, and applied as panchromatic organic sensitizers in I−/I 3 − -based dye-sensitized solar cells (DSSCs). The asymmetric coumarin–phthalocyanine dyad analogue (OAPc) and the symmetric coumarin-phthalocyanine dyad analogue

  两种新型香豆素取代的酞菁染料（CAPC和CSPC）具有不同的连接单元，使用羧基作为电子受体和喷射器，设计，合成，和作为全色有机增感剂施加在我- / I 3 - 染料敏化太阳能电池（DSSC）。还合成了不对称香豆素-酞菁二联体类似物（OAPC）和对称香豆素-酞菁二联体类似物（COPc）进行比较。通过吸收光谱法，循环伏安法和热重分析法研究了这些染料的结构-性质关系。接头的性质极大地影响了紫外线（UV-Vis）吸收。值得注意的是，对π共轭香豆素-酞菁二聚体CAPC和CSPc的调制导致了大的红移（高于710 nm的Q波段）。特别是二元CAPC在450-650 nm的光谱窗口中显示出明显的强烈吸收。染料的电化学数据表明，偶氮双键香豆素-酞菁双染料具有较低的E HOMO值，这可能有利于抑制电子从TiO 2的导带向氧化染料的反向转移，这是因为电解质容易还原氧化的染料。热重分析表明，三种香豆素-酞菁双染料
• High-selective room-temperature NO₂ sensors based on a coumarin-substituted tris(phthalocyaninato) europium
  作者：Yanling Wu、Chuangyu Wei、Hongyuan Wang、Zhuang Mei、Qianli Xing、Jie Su、Zeyu Ning、Yanli Chen、Jianzhuang Jiang

  DOI：10.1142/s1088424621500681

  日期：2021.10

  A novel coumarin-substituted phthalocyaninato triple-decker complex, Eu₂[Pc(Cou)₄]₃ is designed and synthesized successfully. Introduction of the coumarin substituents onto the periphery of a phthalocyanine ring in the sandwich-type phthalocyaninato triple-decker not only increased the solubility and improved the film-forming ability, but also importantly ensured the suitable HOMO and LUMO energy levels. The solution-processed thin film of the Eu₂[Pc(Cou)₄]₃ was prepared by a simple and low-cost quasi–Langmuir–Shäfer (QLS) method and applied as the gas sensor for the detection of NO₂. Importantly, within the dynamic exposure period of 1 min, balanced, stable, a reproducible [Formula: see text]-type response to electron-accepting gas NO₂ in the range of 4–35 ppm, was revealed, based on the QLS film of Eu₂[Pc(Cou)₄]₃ complex at room temperature, dependant on the optimized molecular packing in [Formula: see text]-aggregation mode with a large specific surface area and good film conductivity.

  我们设计并成功合成了一种新型香豆素取代的酞菁三迭代复合物 Eu2[Pc(Cou)4]3。将香豆素取代基引入夹层型酞菁三迭合络合物中的酞菁环外围，不仅增加了溶解度，提高了成膜能力，更重要的是确保了合适的 HOMO 和 LUMO 能级。通过简单、低成本的准朗缪尔-舍弗（QLS）法制备了 Eu2[Pc(Cou)4]3溶液加工薄膜，并将其用作检测二氧化氮的气体传感器。重要的是，基于室温下 Eu2[Pc(Cou)4]3 复合物的 QLS 薄膜，在[式中：见正文]聚合模式下的优化分子堆积具有较大的比表面积和良好的薄膜导电性，在 1 分钟的动态暴露时间内，对 4-35 ppm 范围内的电子接受气体 NO2 显现出平衡、稳定和可重现的[式中：见正文]型响应。
• The effect of coadsorbent and solvent on the photovoltaic performance of 2,9,16,23-Tetrakis(7-coumarinoxy-4-methyl)-phthalocyaninatocopper-sensitized solar cells
  作者：Fei Zhang、Shi-Rong Wang、Xiang-Gao Li、Yin Xiao、Jun-Jie Guo

  DOI：10.1016/j.molstruc.2015.11.074

  日期：2016.3

  The synthesis, characterization and thermal properties of CuPc-Cou were reported and the effects of chenodeoxycholic acid (CHENO) as a coadsorbent and the solvent on the solar cell's performance were investigated. The ground state absorbance of CuPc-Cou showed the molar extinction coefficients as high as 2.90 x 10(4) dm(3) mol(-1) cm(-1) in DMF and 2.74 x 10(4) dm(3) mol(-1) cm(-1) in CH2Cl2. The thermal stability studies indicated that CuPc-Cou was stable up to 370 degrees C. Furthermore, HOMO and LUMO energies made it clear that CuPc-Cou can be used as a sensitizer for DSSC. Adding CHENO onto TiO2 nanoparticles not only reduced the adsorption of phthalocyanine sensitizers but also prevented the aggregation behavior, leading to different photovoltaic performance. The open circuit voltage of the solar cells with CHENO coadsorbent increased due to the enhanced electron lifetime in TiO2 nanoparticles coupled with the band edge shift of TiO2 to negative potentials. The optimal dye adsorption condition of the TiO2 electrode was found to be 3 x 10(-4) M CuPc-Cou solution containing 6.0 mM CHENO in dichloromethane, which could contribute to improve the PCE by 69% as compared to the solar cell fabricated with TiO2 electrode sensitized by the CuPc-Cou in absence of CHENO and the optimal condition in DMF. It indicated that CuPc-Cou in DMF was easy to aggregate than in CH2Cl2 for the solvent effect. (C) 2015 Elsevier B.V. All rights reserved.