α-Cyan-4'-hydroxy-4-nitro-stilben

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-Cyan-4'-hydroxy-4-nitro-stilben
• 英文别名: * 3-<4-Hydroxy-phenyl>-2-<4-nitro-phenyl>-acrylonitril；4-nitro-4'-hydroxy-α-cyanostilbene；4-Nitro-4'-hydroxy-alpha-cyanostilbene；3-(4-hydroxyphenyl)-2-(4-nitrophenyl)prop-2-enenitrile
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: XQQQEGKTKATSSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-Cyan-4'-hydroxy-4-nitro-stilben 在 乌洛托品 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  An unusual AIE fluorescent sensor for sequentially detecting Co2+-Hg2+-Cu2+ based on diphenylacrylonitrile Schiff-base derivative

  摘要：

  Aggregation-induced emission (AIE) molecules with strong fluorescence in aggregated states are favourable for preparing the organic fluorescence sensor in aqueous phase. In this work, a red fluorescent sensor 5 based on AIE diphenylacrylonitrile Schiff-base derivative was prepared in yield of 83.7%. Sample 5 exhibited strong AIE property in water with red fluorescence at lambda(ex) = 620 nm and the Stokes shift was as large as 260 nm. The experiments of sensing series of metallic ions suggested that sample 5 possessed the sequentially detecting abilities for Co2+-Hg2+-Cu2+, which was observed firstly for organic fluorescence sensor. The fluorescence of sample 5 was quenched rapidly in presence of Co2+, then recovered by adding Hg2+ and quenched once more by further adding Cu2+. The detection limits for Co2+, Hg2+ and Cu2+ were 0.0937, 0.0221, and 0.0988 mu M, respectively. The sensor mechanism was confirmed by fluorescence titration, H-1 NMR and MS spectra, indicating the 2:1 stoichiometric ratios of sample 5 with ions. The sensor for ions was successfully applied in test paper, exhibiting good practical application potential for detecting Co2+-Hg2+-Cu2+ sequentially. Sample 5 showed good bioimaging performance on living cell. The fluorescence of living cells with sample 5 also displayed the similar change of quenching-recovering-quenching by adding Co2+-Hg2+-Cu2+ orderly, implying the good ions-detecting prospect in living body environment.

  DOI：

  10.1016/j.dyepig.2019.107590
• 作为产物：
  描述：

  对硝基苯乙腈 、 对羟基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以60%的产率得到α-Cyan-4'-hydroxy-4-nitro-stilben
  参考文献：
  名称：

  一种简单有效的修饰PCBM的方法，以用作高效大容量异质结太阳能电池中的电子受体

  摘要：

  [6,6]-苯基-C-61-丁酸甲酯（PCBM）和聚（3-己基噻吩）（P3HT）分别是聚合物太阳能电池（PSC）中使用最广泛的受体和供体材料。但是，PCBM的低LUMO（最低未占用分子轨道）能级限制了基于P3HT的PSC的开路电压（V oc）。本文报道了一种简单，低成本，有效的修饰PCBM并提高其吸收率的方法，该方法可以扩展到所有具有酯结构的富勒烯衍生物。特别地，将PCBM水解为羧酸，然后转化为相应的羰基氯。后者与4-硝基-4'-羟基-α-氰基二苯乙烯缩合，得到改性的富勒烯F。由于有机部分的增加，它比PCBM在普通有机溶剂中的溶解度更高。在250-900 nm的范围内，溶液和F薄膜均显示出比PCBM更强的吸收能力。F和PCBM的电化学性质和电子能级通过循环伏安法测量。F的LUMO能级比PCBM高0.25 eV。基于F的P3HT的PSC显示出0.86 V的更高V oc和8.5 mA cm -2的短路电流（J

  DOI：

  10.1002/adfm.201001807

文献信息

• 一种用于检测铜离子的吡啶席夫碱结构荧光探针及其制备方法与应用
  申请人：福建师范大学

  公开号：CN109970634B

  公开（公告）日：2022-03-15

  本发明涉及一种用于检测铜离子的吡啶席夫碱结构荧光探针及其制备方法与应用。所述的荧光探针是一种带羟基的氰基二苯基乙烯化合物。制备时将4‑硝基苯乙腈与4‑羟基苯甲醛室温反应得到化合物2；将化合物2与六亚甲基四胺以摩尔比1:2~4的比例，加入到三氟乙酸中进行回流反应得到化合物3；将化合物3与2‑氨基吡啶以1:1.1~1.5溶解于甲醇中，冷凝回流后，冷却至室温，提纯得到荧光探针。本发明制备的化合物1可用于高选择性灵敏检测铜离子，这对于复杂环境中铜离子的检测有重要的现实应用价值。
• Synthesis and characterization of a bis-methanofullerene-4-nitro-α-cyanostilbene dyad as a potential acceptor for high-performance polymer solar cells
  作者：Boram Kim、Hye Rim Yeom、Won-Youl Choi、Jin Young Kim、Changduk Yang

  DOI：10.1016/j.tet.2012.05.114

  日期：2012.8

  We report the synthesis, characterization, and electrochemical properties of bis-PCBM dyad containing 4-nitro-α-cyanostilbene units for potential usage in efficient organic solar cells. The bis-PCBM dyad is fully characterized by NMR, UV–vis absorption, and electrochemical cyclic voltammetry. It is found that the presence of 4-nitro-α-cyanostilbenes affects the cyclic voltammetry and absorption spectrum

  我们报道了含有4-硝基-α-氰基二苯乙烯单元的bis-PCBM dyad的合成，表征和电化学性能，可用于高效有机太阳能电池。所述双- PCBM成对完全通过NMR，UV-Vis吸收和电化学循环伏安法。发现4-硝基-α-氰基苯甲酸酯的存在对循环伏安法和吸收光谱的影响很小。而双官能化富勒烯笼中的56π电子系统显着影响电化学和光物理性质，与PCBM相比，导致LUMO上移并吸收更宽。尽管基于P3HT / bis-PCBM dyad的常规电池和倒置电池的效率由于与优化的高性能PSC相比，初步结果较低，因此可以相信，通过成功地对P3HT / bis-PCBM dyad细胞进行设备优化，可以提高效率。
• Simple sensitizers of low band gap based on 4-nitro-α-cyanostilbene prepared from a one-step reaction for efficient dye-sensitized solar cells
  作者：J.A. Mikroyannidis、D.V. Tsagkournos、P. Balraju、G.D. Sharma

  DOI：10.1016/j.orgel.2010.05.002

  日期：2010.7

  Two simple dyes D1 and D2 based on 4-nitro-alpha-cyanostilbene were conveniently synthesized from a one-step reaction. These dyes were prepared from the condensation of 4-carboxybenzaldehyde or 4-hydroxybenzaldehyde with 4-nitrobenzyl cyanide to afford 4-nitro-4'-carboxy-alpha-cyanostilbene (D1) and 4-nitro-4'-hydroxy-alpha-cyanostilbene (D2) respectively. Photophysical and electrochemical properties of the dyes were investigated by UV-vis spectroscopy and cyclic voltammetry. Their absorption spectra were broad with long-wavelength absorption maximum at 617-655 nm and optical band gap of 1.63 eV. These two dyes were used as sensitizers in quasi solid state dye-sensitized solar cells (DSSCs). Photovoltaic devices with D1 showed a maximum monochromatic incident photon to current efficiency (IPCE) of 70% and overall power conversion efficiency (PCE) of 4.8%, under illumination intensity 100 mW/cm(2). The photovoltaic performance of the cell with D-2 was lower because of less dye loading on the TiO2 surface, since it has OH anchoring group, and lower electron lifetime. Additionally, we have investigated the photovoltaic response of the DSSCs with nitrogen doped TiO2 photoanode and found that the PCE has been enhanced. The enhancement in PCE has been attributed to the increase in open circuit voltage and fill factor. (c) 2010 Elsevier B.V. All rights reserved.