3-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]propanoic acid | 303981-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]propanoic acid
• CAS: 303981-49-9
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: AWKAEIFKJFSVOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]propanoic acid 以 氘代二甲亚砜 为溶剂， 生成 1-(beta-羧基乙基)-3,3-二甲基-6'-硝基螺(吲哚啉- 2,2'-2H-苯并吡喃)
  参考文献：
  名称：

  使用核磁共振和原位辐照装置研究光致变色模型系统

  摘要：

  通过 NMR 光谱详细研究了光致变色模型系统的切换行为，以提高对化合物本身的理解，并提供深入了解含有螺吡喃/部花青单元的光可切换（聚合物）材料的组成趋势的方法。除了在磁体外部（非原位）进行的经典辐照外，还测试了核磁共振波谱仪（原位）内部的辐照装置。介绍了这两种设置，描述了它们的优点和缺点以及它们的局限性，并建议了未来光致变色材料研究的设置。

  DOI：

  10.1002/mrc.4403
• 作为产物：
  描述：

  1-(beta-羧基乙基)-3,3-二甲基-6'-硝基螺(吲哚啉- 2,2'-2H-苯并吡喃) 生成 3-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]propanoic acid
  参考文献：
  名称：

  通过开环易位聚合反应制备的新型光致变色吲哚并苯并螺并吡喃型均聚物的合成和光谱性质

  摘要：

  通过紧张的双环吲哚并苯并螺并吡喃衍生物的开环易位聚合反应，制备了三种新型的基于光致变色的吲哚并苯并螺并吡喃衍生物的均聚物。均聚物可溶于常见的有机溶剂，并通过凝胶渗透色谱分析确定显示出异常高的多分散性。溶液中的紫外可见吸收光谱分析表明，保留了各个单体具有吸引力的光致变色行为。

  DOI：

  10.1016/j.dyepig.2009.12.002

文献信息

• Multi-responsive supramolecular hydrogels based on merocyanine–peptide conjugates
  作者：Wei Wang、Jing Hu、Mengmeng Zheng、Li Zheng、Huan Wang、Yan Zhang

  DOI：10.1039/c5ob01912e

  日期：——

  Stimuli-responsive hydrogels are “smart” materials with diverse applications. We now report short peptide conjugates with merocyanine (MC) that are able to form stimuli-responsive hydrogels. Systematic investigation reveals that merocyanine is a highly effective promoter for the self-assembly of its oligopeptide conjugates. Hydrogels formed by MC–peptide conjugates showed responses towards light and

  刺激响应水凝胶是具有多种应用的“智能”材料。我们现在报告与花青素（MC）能够形成刺激响应水凝胶的短肽共轭物。系统研究表明，花青素是其寡肽缀合物自组装的高效启动子。MC-肽结合物形成的水凝胶显示出对光和热的响应，其溶胶-凝胶相变可通过相应的螺吡喃部分的反向光致变色来控制。令人印象深刻的是，MCI –RGD共轭物形成了一种超分子水凝胶，对多种刺激具有响应，包括可见光照射，pH值变化和Ca 2+离子的存在。MCI上的可擦除光刻演示了–RGD水凝胶使用可见光进行书写，并进行了加热和冷却处理以擦除多个回合，而不会显着降低灵敏度。
• Micro-environmental fine-tuning of electronic and kinetic properties of photochromic dyes
  作者：Jamie Whelan、Dalia Abdallah、James Wojtyk、Erwin Buncel

  DOI：10.1039/c0jm00585a

  日期：——

  Despite the recognition of the importance of Spiropyran (SP)–Merocyanine (MC) photochromic materials in molecular switching, the majority of studies have been reported in solution with relatively few in the solid-state as required in modern displays and other devices. In contrast, the present work bridges solution, condensed phase and solid-phase media and is to our knowledge the first micro-environmental study on electronic and kinetic effects for the SP–MC system. Expanding on our previous work we have investigated the photochromic properties of an SP molecule (1b) attached to a 100 μm commercially available polystyrene micro-particle (Wang Resin). The thermal MC → SP reversion kinetics (5a,b → 4a,b and 2a,b → 1a,b) which reflect the critical lifetime of the open MC form were measured. Reduction in kobs of thermal reversion, MC → SP, up to two orders of magnitude, and a blue-shift up to 58 nm was observed with the potential for tailoring or fine tuning. The use of polymeric micro-particles in controlling both electronic and kinetic properties of photochromic molecular switches has been highlighted.

  尽管人们已经认识到螺吡喃（SP）-花青素（MC）光致变色材料在分子转换中的重要性，但大多数研究报告都是在溶液中进行的，而在固态中进行的研究相对较少，而这正是现代显示器和其他设备所需要的。相比之下，目前的研究在溶液、凝聚相和固相介质之间架起了桥梁，据我们所知，这是首次对 SP-MC 系统的电子和动力学效应进行微环境研究。在先前工作的基础上，我们研究了附着在 100 μm 市售聚苯乙烯微粒（王氏树脂）上的 SP 分子（1b）的光致变色特性。测量了反映开放 MC 形式临界寿命的热 MC → SP 还原动力学（5a,b → 4a,b 和 2a,b → 1a,b）。观察到热还原 kobs（MC → SP）降低了两个数量级，蓝移高达 58 纳米，具有定制或微调的潜力。聚合物微粒在控制光致变色分子开关的电子和动力学特性方面的应用得到了强调。
• Effects of metal ion complexation on the spiropyran–merocyanine interconversion: development of a thermally stable photo-switch
  作者：James T.C. Wojtyk、Erwin Buncel、Peter M. Kazmaier

  DOI：10.1039/a804908d

  日期：——

  Spectrophotometric absorption and fluorescence measurements of spiropyrans 2 and 3 modified with chelating functionalities, in the presence of Ca2+ and Zn2+, provide evidence of a thermally stable spiropyran–merocyanine photoswitch that is modulated by the metal cations.

  在 Ca2+ 和 Zn2+ 的存在下，对用螯合功能修饰的螺吡喃 2 和 3 进行的分光光度吸收和荧光测量，证明了一种热稳定的螺吡喃珀青色光开关受金属阳离子的调节。
• Holographic relaxation spectroscopy of a benzospiropyran in mixtures of water and dioxane
  作者：Danny G. Miles、Patrick D. Lamb、Kee Woo Rhee、Charles S. Johnson

  DOI：10.1021/j150642a011

  日期：1983.11
• Photo-dynamic and fluorescent zinc complex based on spiropyran ligand
  作者：Flávio B. Miguez、Thiago G. Menzonatto、Jorge Fernandes Z. Netto、Igor M.S. Silva、Thiago Verano-Braga、Juliana Fedoce Lopes、Frederico B. De Sousa

  DOI：10.1016/j.molstruc.2020.128105

  日期：2020.7

  Spiropyrans are among a class of organic molecules widely studied as molecular photoswitches. A photochromic and solvatochromic spiropyran-containing Zinc (II) complex (ZnMC) was successfully synthesized and characterized, and its chromic properties were studied. A solid complex was isolated through a precipitation process induced by UV radiation. The binding specificities were studied by FTIRATR spectroscopy and DFT calculations, demonstrating that phenolate and carboxylic acid are the binding sites of merocyanine. Mass spectrometry and computational methods revealed the possibility of two complexes with different geometries, tetrahedral and octahedral; the complex with tetrahedral characteristics proved to be more stable and abundant. ZnMC solvatochromic properties were analyzed, presenting a wide variation in its absorption band in the visible region. We addressed the issue of ZnMC photodegradation in different solvents, and the observed absorbance did not vary after the first cycles for acetonitrile, while, in tetrahydrofuran, the absorbance decayed throughout the 48 cycles of switching between UV and visible light irradiation. (C) 2020 Elsevier B.V. All rights reserved.