2-(3-cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile | 902465-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-(3-cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile
• 英文别名: 2-(3-cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)propanedinitrile；4-cyano-3-methyl-5-dicyanomethylene-2-oxo-3-pyrroline；tricyanopyrroline；TCP；2-(3-Cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile；2-(3-cyano-4-methyl-5-oxopyrrol-2-ylidene)propanedinitrile
• CAS: 902465-05-8
• 化学式: C₉H₄N₄O
• 分子量: 184.157
• InChiKey: KRHYVDPRGSPVRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.58h， 生成 2-(1-benzyl-4-(4-(bis(2-((tert-butyldimethylsilyl)oxy)ethyl)amino)styryl)-3-cyano-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile
  参考文献：
  名称：

  Synthesis and electro-optic activities of novel polycarbonates bearing tricyanopyrroline-based nonlinear optical chromophores with excellent thermal stability of dipole alignment

  摘要：

  Two series of novel electro-optic (EO) polycarbonates incorporating two kinds of tricyanopyrroline-based nonlinear optical (NLO) chromophores were designed and synthesized. These new polycarbonates were prepared through the facile copolymerization of dial NLO chromophores and bisphenol A bis(chloroformate), and the successful preparations were demonstrated by H-1 NMR and Fourier transform infrared (FT-IR) spectra. These polycarbonates possessed good thermal stabilities and also showed higher glass transition temperatures (T-g) in the range of 156-165 degrees C. After corona poling, the EO coefficients (r(33)) of two poled polycarbonates films were up to 52 pm/V (PC-DTCPC-Ph-2) and 46 pm/V (PC-DTCPCFPh-2) at the wavelength of 1310 nm. The higher T(g)s endow the polycarbonates' poled films with good temporal stability of poling-induced dipole alignment, and the resulting poled films of PC-DTCPC-Ph-2 and PC-DTCPC-FPh-2 could retain 95% and 93% of the initial EO activities at 85 degrees C for more than 500 h respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.09.042
• 作为产物：
  描述：

  丙酮酸乙酯 、 2-氨基-1-丙烯基-1,1,3-三甲腈 以 乙醇 为溶剂， 生成 2-(3-cyano-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile
  参考文献：
  名称：

  基于三氰基吡咯啉的比色 NIR 探针，用于快速“肉眼”检测氟离子

  摘要：

  在此，开发了两种基于三氰基吡咯啉的 NIR 染料（TCP-Tph 和 TCP-HyDe）。这些 NIR 染料对溶剂极性和溶剂的性质高度敏感，并在溶液中显示出反向溶剂化显色特性。两种染料都可作为探针，在各种阴离子上“肉眼”选择性检测氟化物离子。已在溶液中研究了建立探针与氟离子之间相互作用的位点特异性机理研究。此外，这些探头还用于高效实时监测牙膏（溶液）和污水中的氟离子。还开发了一种具有成本效益的纸基氟化物检测试剂盒（固态）。

  DOI：

  10.1016/j.dyepig.2023.111376

文献信息

• Nonlinear optical activity of push–pull indolizine-based chromophores with various acceptor moieties
  作者：Alexey A. Kalinin、Guzel M. Fazleeva、Timur I. Burganov、Liliya N. Islamova、Alina I. Levitskaya、Yulia B. Dudkina、Gulnara R. Shaikhutdinova、Gulshat G. Yusupova、Maxim A. Smirnov、Tatyana A. Vakhonina、Nataliya V. Ivanova、Ayrat R. Khamatgalimov、Sergey A. Katsyuba、Yulia H. Budnikova、Irek R. Nizameev、Marina Yu. Balakina

  DOI：10.1016/j.jphotochem.2018.07.018

  日期：2018.9

  respectively, good agreement with DFT estimations is obtained. The nonlinear optical coefficient for poled PMMA-based films, containing 20 wt% of isomeric indolizine chromophores with weaker dicyanomethylene (DCM) acceptor and with π- bridge expanded by isophorone moiety, achieves 36 pm/V, thus exceeding those for materials containing chromophores with stronger Ph-TCF or Hex-TCP acceptors and with short vinylene

  首次研究并比较了具有不同受体部分的基于吲哚嗪的推挽发色团的非线性光学（NLO）活性。所有发色团在光谱的可见（橙红色）部分均显示出较强的吸收带，其ε为。10 5 L∙cm -1 ∙M -1特别取决于介质极性。用Hex-TCP代替Ph-TCF受体会导致第一个超极化率值增加两倍。通过电化学方法估算的能隙按系列ΔE1a ，b >ΔE3a ，b >ΔE2a ，b减小对于分别具有Ph-TCF，DCM和Hex-TCP受体的化合物，与DFT估计值具有良好的一致性。极化PMMA基薄膜的非线性光学系数达到36 pm / V，包含具有20重量％的异构吲哚嗪发色团，较弱的二氰基亚甲基（DCM）受体和被异佛尔酮部分扩展的π桥的非线性光学系数，因此超过了包含更强的Ph-TCF或Hex-TCP受体，并带有短的亚乙烯基π桥。
• 含有三蝶烯刚性立体结构的发色团分子及其合 成方法和应用
  申请人：中国科学院理化技术研究所

  公开号：CN103373990B

  公开（公告）日：2016-03-09

  本发明涉及含有三蝶烯刚性立体结构的发色团分子及其合成方法，以及该含有三蝶烯刚性立体结构的发色团分子在聚合物电光材料中的应用。本发明是利用N-苯基马来酰亚胺与蒽的环加成反应，再通过反应连接上如“碳碳双键”或“噻吩类”结构的电子桥部分和如“三氰基呋喃”或“三氰基吡咯啉”结构的电子受体部分，得到结构如下所示的含有三蝶烯三维刚性立体结构的发色团分子。将本发明的含有三蝶烯刚性立体结构的发色团分子掺杂至聚合物(如无定型聚碳酸酯APC)中，经极化处理，可得到高性能的聚合物电光材料。本发明的含有三蝶烯刚性立体结构的发色团分子易于合成和分离。
• A novel molecular probe for the detection of phosphorylated proteins
  作者：Yongkang Zeng、Yanfang Wang、Na Yang、Yi Liu

  DOI：10.1515/hc-2017-0264

  日期：2018.4.25

  The compound ZKY-1 with a D-π-A structure was designed and synthesized in four steps. It undergoes complexation with a tetravalent zirconium ion and the complex can be used for the detection of phosphorylated proteins. The detection limit is estimated to be 100 nm in vitro. The successful detection of phosphorylated proteins in placental tissue samples indicates that this probe holds great potential for clinical diagnosis.

  具有D-π-A结构的化合物ZKY-1经过四个步骤的设计和合成。它与四价锆离子发生络合作用，该络合物可用于检测磷酸化蛋白。检测限度估计为100 nm 体外。在胎盘组织样本中成功检测到磷酸化蛋白表明，该探针具有很大的临床诊断潜力。

• Pyrroline chromophores
  申请人：University of Washington

  公开号：US07307173B1

  公开（公告）日：2007-12-11

  Electron acceptor compounds, nonlinear optical chromophores, methods for making the compounds and chromophores, and materials and electro-optic devices that include the chromophores.

  电子受体化合物，非线性光学色团，制备这些化合物和色团的方法，以及包含这些色团的材料和电光器件。
• Formyl Derivatives of Amino-Substituted Polyfluorotriphenyl-4,5-dihydro-1H-pyrazoles: Synthesis and Use as Donor Blocks of Nonlinear Optical Chromophores
  作者：V. V. Shelkovnikov、N. A. Orlova、I. Yu. Kargapolova、K. D. Erin、A. M. Maksimov、A. A. Chernonosov

  DOI：10.1134/s1070428019100087

  日期：2019.10

  5-dihydro-1H-pyrazoles containing various amine residues in the fluorinated benzene ring have been synthesized and used as donor building blocks in the synthesis of donor–acceptor dyes as potential chromophores for nonlinear electro-optics. Effects of substituents in the donor and acceptor moieties of the obtained chromophores on their spectral characteristics have been studied.

  合成了一系列在氟化苯环中含有各种胺残基的多氟代三苯基-4,5-二氢-1 H-吡唑的新甲酰基衍生物，并将其用作合成供体-受体染料的供体构件，作为潜在的发色团。非线性电光学。研究了所得生色团的供体和受体部分中的取代基对其光谱特性的影响。