1',3',3'-trimethylspiro[chromene-2,2'-indolin]-6-yl acrylate | 724460-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1',3',3'-trimethylspiro[chromene-2,2'-indolin]-6-yl acrylate
• 英文别名: 1',3',3'-trimethyl-6-acryloyloxyspiro[2H-1-benzopyran-2,2'-indoline]；SPAA；1',3',3'-Trimethylspiro[chromene-2,2'-indolin]-6-ylacrylate；(1',3',3'-trimethylspiro[chromene-2,2'-indole]-6-yl) prop-2-enoate
• CAS: 724460-11-1
• 化学式: C₂₂H₂₁NO₃
• 分子量: 347.414
• InChiKey: BRBBYZGMQNNZQV-UHFFFAOYSA-N

物化性质

• 沸点：
  502.3±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯酰氯 、 1’,3’,3’-三甲基-6-羟基螺环 以 甲苯 为溶剂， 生成 1',3',3'-trimethylspiro[chromene-2,2'-indolin]-6-yl acrylate
  参考文献：
  名称：

  Photo-reversible Pb2+-complexation of thermosensitive poly(N-isopropyl acrylamide-co-spiropyran acrylate) in water

  摘要：

  利用一种由 N-异丙基丙烯酰胺和螺丙基丙烯酸酯组成的合成共聚物，在较低的临界溶液温度下实现了纯水环境中 Pb2+ 的光可逆络合，并表现出热敏相变。

  DOI：

  10.1039/b407342h

文献信息

• Characteristic Phase Transition of Aqueous Solution of Poly(<i>N</i>-isopropylacrylamide) Functionalized with Spirobenzopyran
  作者：Kimio Sumaru、Mitsuyoshi Kameda、Toshiyuki Kanamori、Toshio Shinbo

  DOI：10.1021/ma049661x

  日期：2004.6.1

  synthesized by modifying poly(N-isopropylacrylamide) with spirobenzopyran. The phase transition properties of the aqueous solution of this copolymer exhibited a logic-gate response to the light irradiation and to increased temperature, which has three different modes depending on the pH of the solution. Especially, a great increase in turbidity was observed even in dilute aqueous solution containing only 0

  通过用螺并苯并吡喃改性聚（N-异丙基丙烯酰胺）合成了一种新型的功能共聚物。该共聚物水溶液的相变性能表现出对光照射和温度升高的逻辑门响应，取决于溶液的pH值，其具有三种不同的模式。特别是，即使共聚物仅含有1.1摩尔％的螺并苯并吡喃，即使在仅含有0.10重量％的共聚物的稀水溶液中，也观察到浊度的极大增加。还证实了在相同系统的热诱导相变的影响下，螺并苯并吡喃残基被异构化。紧密连接在一起的热响应性聚合物和光响应性发色团的主链相互影响。
• Photo-reversible and selective Cu2+ complexation of a spiropyran-carrying sulfobetaine copolymer in saline solution
  作者：Takayuki Suzuki、Yuki Hirahara、Kaori Bunya、Hiraku Shinozaki

  DOI：10.1039/b921169a

  日期：——

  A sulfobetaine copolymer (1) carrying a photochromic spiropyran residue was synthesized, which reversibly isomerized between the closed and open forms in pure water and in saline by irradiation with visible light. The thermodynamic stability of the open form of the spiropyran methacrylate (SPMA) units of compound 1 was reduced upon increasing NaCl concentration. In addition, photo-reversible and selective Cu2+ complexation in saline solution ([NaCl] = 1.0 wt%) was achieved using compound 1 with metal ions (Cu2+, Zn2+, Ni2+, or Co2+). Covalently cross-linked compound 1 showed selective Cu2+ adsorption in pure water. In contrast, the other metal ions were increasingly adsorbed as NaCl concentration increased, resulting in lower selectivity of Cu2+ ion adsorption with 1, e.g., the ratios of adsorption of Cu2+, Zn2+, Ni2+, and Co2+ with 1 in 10 wt% saline were 73, 20, 10, and 3%, respectively, while only Cu2+ adsorption was observed in a solution of 1.0 wt% NaCl. Because the stability of the open form of the SPMA units and the metal complexation of 1 were influenced by NaCl concentration, the electrostatically cross-linked networks of the zwitterionic sulfobetaine units of 1 may be loosened by NaCl addition, resulting in easy entry of metal ions into the network. The order of metal complexation among the four metals corresponded to the Irving–Williams series. Hydrogen-bonded networks of water molecules also may contribute to the relatively ineffective selective adsorption of Cu2+ ions by 1 compared to the electrically neutral spiropyran-carrying copolymer of N-isopropylacrylamide, 2.

  合成了带有光致变色螺吡喃残基的磺基甜菜碱共聚物(1)，该共聚物在纯水和盐水中通过可见光照射在闭合和开放形式之间可逆地异构化。化合物 1 的螺吡喃甲基丙烯酸酯 (SPMA) 单元的开放形式的热力学稳定性随着 NaCl 浓度的增加而降低。此外，使用化合物 1 与金属离子（Cu2+、Zn2+、Ni2+ 或 Co2+）在盐水溶液（[NaCl] = 1.0 wt%）中实现了光可逆和选择性 Cu2+ 络合。共价交联的化合物 1 在纯水中表现出选择性吸附 Cu2+。相反，随着 NaCl 浓度的增加，其他金属离子的吸附量增加，导致 Cu2+ 离子对 1 的吸附选择性较低，例如，10 wt% 盐水中 Cu2+、Zn2+、Ni2+ 和 Co2+ 对 1 的吸附比例为 73分别为 20%、10% 和 3%，而在 1.0 wt% NaCl 溶液中仅观察到 Cu2+ 吸附。由于SPMA单元开放形式的稳定性和1的金属络合受到NaCl浓度的影响，1的两性离子磺基甜菜碱单元的静电交联网络可能会因NaCl的添加而松弛，导致金属离子容易进入进入网络。四种金属之间的金属络合顺序对应于欧文-威廉姆斯系列。与电中性的带有螺吡喃的 N-异丙基丙烯酰胺共聚物 2 相比，水分子的氢键网络也可能导致 Cu2+ 离子 1 的选择性吸附相对无效。
• LIGHT- AND HEAT-RESPONSIVE ADSORBENTS AND PROCESS FOR RECOVERY OF SOLUTES
  申请人：Tokyo Denki University

  公开号：EP1679116A1

  公开（公告）日：2006-07-12

  A light- and heat-response adsorbent, having an optically responding ability reversibly showing transition to adsorption and release of a soluble substance in a soluble-substance solution in response to whether light is irradiated or not and a thermally responding ability reversibly showing transition to solubilization and precipitation, or swelling and contraction, in response to temperature, preferably containing a copolymer of monomers including 1',3',3'-trimethyl-6-(acryloyloxy)spiro(2H-1-benzopyran-2,2 '-indole] and N-isopropylacrylamide. Thus, the invention provides an adsorbent functioning both to adsorb and release a soluble substance from and into solution and having higher soluble-substance recovery efficiency.

  一种光和热响应吸附剂，其光学响应能力可逆地显示可溶性物质在可溶性物质溶液中随光照与否而过渡到吸附和释放，热响应能力可逆地显示可溶性物质在可溶性物质溶液中随光照与否而过渡到溶解和沉淀、本发明还提供了一种吸附剂，它具有对温度可逆地显示出溶解和沉淀或膨胀和收缩的转变，最好含有单体的共聚物，这些单体包括 1',3',3'-三甲基-6-（丙烯酰氧基）螺（2H-1-苯并吡喃-2,2'-吲哚）和 N-异丙基丙烯酰胺。因此，本发明提供了一种既能吸附可溶性物质又能将其从溶液中释放出来的吸附剂，具有更高的可溶性物质回收效率。
• Spiropyran Photoisomerization Dynamics in Multiresponsive Hydrogels
  作者：Amos Meeks、Michael M. Lerch、Thomas B. H. Schroeder、Ankita Shastri、Joanna Aizenberg

  DOI：10.1021/jacs.1c08778

  日期：2022.1.12

  and temperature responsivity: acrylamide, acrylic acid, N-isopropylacrylamide, and 2-(dimethylamino)ethyl methacrylate. In acidic and neutral gels, we observe unusual nonmonotonic, triexponential fluorescence dynamics under 405 nm irradiation that cannot be explicated by either the established spiropyran–merocyanine interconversion model or hydrolysis. To explain these results, we introduce an analytical

  光响应性螺吡喃功能化水凝胶已被用于创建可逆光驱动结构，用于从微流体到非线性光学的应用。为特定应用定制螺吡喃功能化水凝胶系统需要了解共聚单体组成如何影响螺吡喃发色团的转换动力学。这种凝胶通常被设计成对不同的刺激（如光、温度和 pH 值）有反应。这些影响的耦合可以显着改变螺吡喃的行为方式，目前尚不为人所知。为了更好地了解响应共聚单体对螺吡喃异构化动力学的影响，N-异丙基丙烯酰胺和甲基丙烯酸2-(二甲氨基)乙酯。在酸性和中性凝胶中，我们观察到在 405 nm 照射下不寻常的非单调三指数荧光动力学，这不能通过已建立的螺吡喃-部花青相互转化模型或水解来解释。为了解释这些结果，我们介绍了螺吡喃相互转化的分析模型，其中包括 H-聚集部花青及其在 405 nm 照射下的光触发解聚。该模型非常适合观察到的荧光动力学，并准确阐明了创建酸性内部凝胶环境如何促进亲水部花青物质快速和完全转化为疏水螺吡喃形式，这是大
• Reversible and Efficient Proton Dissociation of Spirobenzopyran-Functionalized Poly(<i>N</i>-isopropylacrylamide) in Aqueous Solution Triggered by Light Irradiation and Temporary Temperature Rise
  作者：Kimio Sumaru、Mitsuyoshi Kameda、Toshiyuki Kanamori、Toshio Shinbo

  DOI：10.1021/ma0487249

  日期：2004.10.1