(Z)-3-(4-(dimethylamino)phenyl)-2-(4-hydroxyphenyl)acrylonitrile | 1376758-56-3

• 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: (Z)-3-(4-(dimethylamino)phenyl)-2-(4-hydroxyphenyl)acrylonitrile
• 英文别名: (z)-3-(4-(Dimethylamino)phenyl)-2-(4-hydroxyphenyl) acrylonitrile；(Z)-3-[4-(dimethylamino)phenyl]-2-(4-hydroxyphenyl)prop-2-enenitrile
• CAS: 1376758-56-3
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: KPFSVIFTPOTJJQ-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-(dimethylamino)phenyl)-2-(4-hydroxyphenyl)acrylonitrile 、 6-[4-(10-Bromodecyl)piperazin-1-yl]-2-butylbenzo[de]isoquinoline-1,3-dione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 11.0h， 以74.3%的产率得到(Z)-2-[4-[10-[4-(2-butyl-1,3-dioxobenzo[de]isoquinolin-6-yl)piperazin-1-yl]decoxy]phenyl]-3-[4-(dimethylamino)phenyl]prop-2-enenitrile
  参考文献：
  名称：

  Unimolecular Photoconversion of Multicolor Luminescence on Hierarchical Self-Assemblies

  摘要：

  Facile tuning of photophysical properties is highly desirable for boosting the performance and versatility of photoluminescent materials. In an attempt to overcome the challenge of achieving the photoswitching of multicolor luminescence on unimolecular platforms, we here report a novel hierarchical self-assembly of a cyanostilbene-naphthalimide dyad as the realization of phototunable luminescence at the unimolecular level. The work takes advantage of the photoisomerization of the cyanostilbene moiety from the Z form to its E form, which causes a morphological disorder in the molecular self-assembly and gives rise to a dual fluorescent characteristic accompanied by a progressive luminescent color conversion from yellow to green and finally to blue. Such systems with convertible multicolor luminescence might exhibit application potentials for unimolecular selective imaging and labeling, as exemplified by the cell imaging studies presented in this work.

  DOI：

  10.1021/ja400456h
• 作为产物：
  描述：

  对羟基苯乙腈 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 22.0h， 生成 (Z)-3-(4-(dimethylamino)phenyl)-2-(4-hydroxyphenyl)acrylonitrile
  参考文献：
  名称：

  基于α-氰基二苯乙烯的荧光团：聚集诱导的增强发射，溶剂致变色和pH效应†

  摘要：

  合成了一系列被二甲基苯胺，二苯基苯胺和咔唑取代的α-氰基对苯二酚，并研究了它们在均相溶剂，二恶烷-水二元混合物和固态下的光谱性质。Stilbenes（1和4）在均相溶剂中显示出较弱的发射行为，但在水和固态中显示出显着的红移发射以及增强的强度。这种现象是由于聚集引起的增强的发射效应。其他对苯二酚在水和固态中也表现出显着的溶剂变色发光行为，并具有类似的增强发光特性。发射对酸性或碱性强度变化的敏感性确定了这些分子作为荧光探针的实用性。

  DOI：

  10.1039/c4nj01103a

文献信息

• Cholesterol-tethered AIEE fluorogens: formation of self-assembled nanostructures
  作者：Veerabhadraiah Palakollu、Sriram Kanvah

  DOI：10.1039/c5ra04417k

  日期：——

  Design and synthesis of cholesterol conjugated chromophores exhibiting intramolecular charge transfer (ICT) and Aggregation Induced Enhanced Emission (AIEE) and their self-assembling behavior is described.

  描述了胆固醇共轭色团的设计和合成，展示了分子内电荷转移（ICT）和聚集诱导增强发光（AIEE）以及它们的自组装行为。
• Polymeric temperature and pH fluorescent sensor synthesized by reversible addition-fragmentation chain transfer polymerization
  作者：Guofeng Liu、Wei Zhou、Jiaqi Zhang、Ping Zhao

  DOI：10.1002/pola.25995

  日期：2012.6.1

  thermo‐ and pH‐responsive fluorescent signaling parts, respectively, has been synthesized by reversible addition–fragmentation chain transfer polymerization. The copolymer PCN250 (m/n = 250) shows absorbance enhancement or decrease at different pH value. However, the fluorescence intensity of this copolymer shows enhancement with a rise in temperature regardless of pH value in the range of pH = 4–10. In

  由N-异丙基甲基丙烯酰胺（NIPMAM）和（Z）-4-（1-氰基-2-（4-（二甲氨基）苯基）乙烯基）苯基甲基丙烯酸酯（CPMA ）组成的简单结构共聚物聚（NIPMAM- co -CPMA）通过可逆的加成-断裂链转移聚合反应分别合成了作为热响应和pH响应的荧光信号转导单元。共聚物PCN250（m / n= 250）表示在不同pH值下吸光度增加或降低。但是，无论pH = 4-10，pH值越高，该共聚物的荧光强度都会随温度的升高而增强。另外，在高质子浓度下观察到共聚物（PCN250）的荧光抑制。此外，还研究了具有不同组分的共聚物聚（NIPMAM- co- CPMA）的较低临界溶液温度。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年
• A sensitive AIEE probe for amphiphilic compounds
  作者：Veerabhadraiah Palakollu、Anuji K. Vasu、Vijay Thiruvenkatam、Sriram Kanvah

  DOI：10.1039/c5nj02398j

  日期：——

  crystallographic data suggest a zigzag molecular packing arrangement with intermolecular hydrogen bonding between –CN and –OH moieties. This unique observation is exploited as a diagnostic tool to probe amphiphilic compounds in aqueous media. Fluorescence investigations reveal that at lower surfactant concentrations emission due to aggregation is preserved, while at higher surfactant concentrations

  与有机溶剂相比，被二甲基苯胺和羟基取代的α-氰基二苯在水介质中显示出显着的增强的红移现象。这些明显的发射变化归因于分子内旋转受限的聚集。这种观察通常被称为聚集诱导的增强发射（AIEE）。单晶X射线晶体学数据表明–CN和–OH部分之间具有分子间氢键的曲折分子堆积排列。这种独特的观察被用作诊断工具，以探测水性介质中的两亲化合物。荧光研究表明，在较低的表面活性剂浓度下，由于聚集导致的发射得以保留，而在较高的表面活性剂浓度下，总的发射损失了，伴随着胶束结构的变化。使用动态光散射（DLS）和扫描电子显微镜（SEM）实验分别检查表面活性剂对粒径和形貌的影响。这种敏感的AIEE荧光响应也可以通过使用手持式紫外线灯在视觉上观察到。
• Fluorescent Linear Supramolecular Polymer Based on Host-Guest Interactions
  作者：Chenxiao Xiong、Ruyi Sun

  DOI：10.1002/cjoc.201700229

  日期：2017.11

  monomer components are held together by noncovalent interactions, is considered as a promising design principle for functional materials. Linear fluorescent supramolecular polymer assembled on account of electrostatic attractions based host‐guest interaction is synthesized and illustrated here. 1H NMR was involved to ensure the structure of guest and polymer, UV–vis and fluorescent spectra were recorded

  通过非共价相互作用将功能单体成分结合在一起的超分子聚合物的构造被认为是功能材料的一种有前途的设计原则。合成并说明了基于静电吸引的基于主体-客体相互作用组装的线性荧光超分子聚合物。参与1 H NMR以确保客体和聚合物的结构，紫外可见光谱和荧光光谱被记录为读出信号，以研究聚合物的组装过程。进行TEM和AFM测量以确认均一的纳米级分子组装。它显示了将来用作远程读出荧光功能材料的方法。
• Photo-triggered transformation from vesicles to branched nanotubes fabricated by a cholesterol-appended cyanostilbene
  作者：Pengyao Xing、Hongzhong Chen、Linyi Bai、Yanli Zhao

  DOI：10.1039/c5cc02816g

  日期：——

  Vesicles constructed from cholesteryl cyanostilbene could transform into nanotubes upon UV light irradiation, in which the photoluminescence could be fine-tuned.

  由胆固醇氰基芝芊构建的囊泡在紫外光照射下可以转化为纳米管，其中光致发光可以进行微调。