1'-(2-acryloxyethyl)-3',3'-dimethyl-6-nitrospiro(2-H-1-benzopyran-2,2'-indoline)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1'-(2-acryloxyethyl)-3',3'-dimethyl-6-nitrospiro(2-H-1-benzopyran-2,2'-indoline)
• 英文别名: 2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl prop-2-enoate
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: YFPPLUROUFVKRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1'-(2-acryloxyethyl)-3',3'-dimethyl-6-nitrospiro(2-H-1-benzopyran-2,2'-indoline) 生成 2-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]ethyl prop-2-enoate
  参考文献：
  名称：

  FRET Phenomenon in Photoreversible Dual-Color Fluorescent Polymeric Nanoparticles Based on Azocarbazole/Spiropyran Derivatives

  摘要：

  Incorporation of chromophores into a polymer chain results in prominent photoreversibility and fatigue resistance, photostability over the long term, and restriction of the internal conversion (IC). Here, we report the copolymerization of two photoactive monomers with methyl methacrylate via emulsion polymerization in order to obtain photoswitchable dual-color fluorescent nanoparticles. For this purpose, azocarbazole ethyl acrylate (AzoCzEA) and spiropyran ethyl acrylate (SPEA) were synthesized and the fluorescence polymeric latex nanoparticles were prepared correspondingly. FT-IR and (HNMR)-H-1 spectra were used to confirm the structure of novel fluorescent AzoCzEA. UV vis studies of the obtained nanoparticles displayed the spectral features of both AzoCzEA and SPEA under stimuli-irradiation and inclusion of these chromophores into the polymer particles. DSC analysis revealed an increase in Tg of the prepared copolymer, indicating covalently incorporation of the photoactive monomers into the polymer chains. The optimum ratio of two chromophores to achieve complete quenching and highest energy transfer was determined by UV vis spectroscopy. DLS and SEM results demonstrated particle size distribution of 40-80 nm with spherical morphology. Fluorescence spectra revealed remarkable fluorescence resonance energy transfer (FRET) from AzoCzEA to SPEA after UV irradiation at 365 nm and dual-color characteristic of the prepared nanoparticles. Besides, an enhancement in the photoreversibility, photostability, prevention of IC, dye leakage, and aggregation were studied elaborately. The obtained results were attributed to the involvement of such chromophores into the polymeric matrix via covalent bonding. Labeling and tracking of living cells and rewriteable patterning are potential applications for such dual-color fluorescent nanoparticles.

  DOI：

  10.1021/acs.macromol.5b02401
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 哌啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 1'-(2-acryloxyethyl)-3',3'-dimethyl-6-nitrospiro(2-H-1-benzopyran-2,2'-indoline)
  参考文献：
  名称：

  Development of light-responsive porous polycarbonate membranes for controlled caffeine delivery

  摘要：

  为了控制咖啡因的释放，我们开发了光响应膜。与日光下的测量结果相比，在紫外线照射下，膜的咖啡因渗透阻力降低了约 97%。这是通过将具有光致变色单元的聚合物接枝到轨迹边缘聚碳酸酯膜上实现的。多孔聚碳酸酯膜上的共价连接涂层是通过等离子活化膜表面，然后进行等离子诱导接枝聚合而获得的。在涂层过程中对螺环化合物进行共聚，以及用螺环吡喃对预制涂层进行后修饰，均可获得光致变色膜。在共聚过程中，成功合成了五种具有光致变色作用的甲基丙烯酸和丙烯酸螺吡喃以及螺恶嗪。此外，我们还合成了一种具有羧酸功能的螺吡喃，用于后改性工艺。这使我们能够对含有醇或胺基团的聚合物材料进行后修饰，从而获得光致变色材料。对这些光响应膜进行紫外线照射后，膜会产生强烈的颜色变化，表面张力降低，从而降低了咖啡因的抗渗透性。利用 XPS 测定涂层的元素组成、接触角测量表面张力、固态 UV/VIS 测量动力学和稳定性能，以及双光子显微镜测定光致变色物质在多孔膜中的定位。

  DOI：

  10.1039/c3ra44399j

文献信息

• Magneto-responsive photochromic acrylic copolymer nanoparticles: An investigation into the mutual interactions and photoisomerization kinetics
  作者：Alireza Mouraki、Zeinab Alinejad、Samira Sanjabi、Hamid Salehi-Mobarakeh、Ali Reza Mahdavian

  DOI：10.1016/j.polymer.2021.123524

  日期：2021.3

  were investigated. The results revealed the existence of mutual interactions and successful increment in the absorption intensity (up to 176%) and optical stability, 9% changes in the rate of photoisomerization and increment in the half life time of MC isomers. These were achieved in the presence of magnetite as well as enhancement in the magnetic properties by 10% under UV irradiation at 365 nm. Such

  光敏和磁敏智能材料受到了特别关注。在这里，通过微乳液聚合制备了新型的双功能聚丙烯丙烯酸纳米颗粒，其中磁铁矿纳米颗粒（10-15 nm）驻留在芯中，聚（甲基丙烯酸甲酯-共螺吡喃丙烯酸乙酯）（聚（MMA-co-SPEA））位于外壳中。螺吡喃与磁铁矿表面的化学键合提供了它们的近距离，从而导致了以前从未研究过的有效相互作用。螺吡喃（SP）基花青两性离子的激发态与超顺磁性Fe 3 O 4的磁场之间的相互作用对NP进行了调查。结果表明存在相互作用，并且吸收强度（高达176％）和光学稳定性成功增加，光异构化速率发生9％的变化，MC异构体的半衰期增加。这些是在磁铁矿存在下以及在365 nm的紫外线照射下将磁性提高10％时实现的。超顺磁性Fe 3 O 4 NP的磁场与MC中产生的瞬时偶极矩之间的这种协同和双向相互作用可能为制备用于光触发磁开关，磁触发光开关的双响应纳米复合粒子提供一条新途径。以及同步传感和分离探头。
• Photo and Thermo Dual-Responsive Copolymer Surfaces for Efficient Cell Capture and Release
  作者：Yuwei Hao、Hongliang Liu、Guannan Li、Haijun Cui、Lei Jiang、Shutao Wang

  DOI：10.1002/cphc.201701145

  日期：2018.8.17

  overcome the low efficiency of single‐responsive smart surfaces, we have constructed a dual‐responsive smart surface – poly(spiropyran‐co‐N‐isopropylacrylamide) (poly(SP‐co‐NiPAAm))‐grafted silicon nanowire arrays – by combining photo‐responsive SP and thermo‐responsive NiPAAm units for enhancing the efficiencies of cancer‐cell capture and release. These enhanced efficiencies probably originate from

  为了克服单个响应智能表面的效率低，我们已经建立了一个双响应智能表面-聚（spiropyran-共-N异丙基丙烯酰胺）（聚（SP-共-NiPAAm）） -接枝的硅纳米线阵列-通过组合光敏SP和热敏NiPAAm装置可增强癌细胞捕获和释放的效率。这些提高的效率可能源于两个响应性建筑单元的二元协同作用：NiPAAm单元可以降低异构化过程中SP单元之间的空间位阻，而SP单元则可以促进NiPAAm单元的相变。这项研究提供了一种新策略，用于设计对生物医学应用具有有效响应能力的智能材料和表面。
• Device for measuring the concentration of an analyte in the blood or tissue of an animal or a human, particularly a premature infant, in a self-calibrating manner
  申请人：Universität Zürich

  公开号：EP2974656A1

  公开（公告）日：2016-01-20

  The invention relates to a device for measuring the concentration of an analyte in the blood or tissue of a an animal or a human, particularly a premature infant, wherein for measuring said concentration the device comprises a means (30) comprising at least a first and a second permeability with respect to said analyte, wherein the first permeability for said analyte differs from the second permeability for the analyte. Further, the invention relates to a corresponding method.

  本发明涉及一种用于测量动物或人类（尤其是早产儿）血液或组织中分析物浓度的装置，其中，用于测量所述浓度的装置包括一个装置（30），该装置至少包括对所述分析物的第一和第二渗透性，其中，对所述分析物的第一渗透性不同于对分析物的第二渗透性。此外，本发明还涉及一种相应的方法。
• Spiropyran-Conjugated Thermoresponsive Copolymer as a Colorimetric Thermometer with Linear and Reversible Color Change
  作者：Yasuhiro Shiraishi、Ryo Miyamoto、Takayuki Hirai

  DOI：10.1021/ol900188m

  日期：2009.4.2

  A simple copolymer, poly(NIPAM-co-SP), consisting of N-isopropylacrylamide and spiropyran units, behaves as a colorimetric thermometer exhibiting temperature-responsive linear and reversible bathochromic/hypsochromic shift of the absorption spectra under UV irradiation.
• Synthesis of amphiphilic spiropyran-based random copolymer by atom transfer radical polymerization for Co2+ recognition
  作者：Huanqing Cui、Hui Liu、Si Chen、Ruimeng Wang

  DOI：10.1016/j.dyepig.2014.12.008

  日期：2015.4

  An amphiphilic spiropyran-based random copolymer containing methacrylic acid unit has been prepared and investigated with obvious negative solvatochromism in five different solvents. It was found that the polarity of comonomer influenced the photochromic behavior of spiropyran. The synthesized copolymer exhibited a good reversible behavior in aqueous solution: the addition of strong acid promoted the isomerization from spiropyran (SP) to merocyanine (MC), and the inverse process was achieved by the introduction of strong base. Much more importance, the effect of comonomer was utilized for the selective Co2+ recognition. The locations of the maximum absorption peak stay almost as same as MC when it is complexed with Cu2+, Mn2+ and Hg2+. The location, however, moves from 551 nm to 526 nm upon complexation with Co2+. The obvious color change of the solution from purple to claret-red after complexation with Co2+ was observed. This interesting phenomenon is practically convenient for the visual recognition of Co2+. (C) 2014 Elsevier Ltd. All rights reserved.