2-(2-{4-[N,N-di(4-bromophenyl)amino]phenyl}ethenyl)thien-5-al | 1190764-15-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-{4-[N,N-di(4-bromophenyl)amino]phenyl}ethenyl)thien-5-al
• 英文别名: 5-[2-[4-(4-bromo-N-(4-bromophenyl)anilino)phenyl]ethenyl]thiophene-2-carbaldehyde
• CAS: 1190764-15-8
• 化学式: C₂₅H₁₇Br₂NOS
• 分子量: 539.29
• InChiKey: NHPBMPFDPPJQEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-{4-[N,N-di(4-bromophenyl)amino]phenyl}ethenyl)thien-5-al 、 乙硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以40.7%的产率得到
  参考文献：
  名称：

  汞的荧光和比色探针（II）：电子给体和π共轭电桥的可调结构

  摘要：

  一系列新的分子内电荷转移（ICT）分子（化合物1，2，和3）通过各种供电子基团的噻吩附连到三苯胺骨架与醛基作为电子受体进行合成。基于乙硫醇与醛之间的保护反应，制备了相应的二硫缩醛（化合物S1，S2和S3），用作Hg 2+离子的新型比色和荧光化学传感器。此外，化合物S1还用于构建针对Hg 2+的基于化学反应的共轭聚合物探针（PS1）离子。在低至10 n M Hg 2+的存在下，化合物PS1的荧光强度出现明显变化。依赖于时间的DFT计算证实了传感过程是由ICT介导的。此外，化合物S1已成功应用于比例成像荧光法检测HeLa细胞中Hg 2+的显微成像。

  DOI：

  10.1002/chem.201102376
• 作为产物：
  描述：

  4-二苯胺基苯甲醛 在 potassium tert-butylate 、 溴 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(2-{4-[N,N-di(4-bromophenyl)amino]phenyl}ethenyl)thien-5-al
  参考文献：
  名称：

  Suzuki polycondensation and post-polymerization modification toward electro-optic perfluorocyclobutyl (PFCB) aryl ether polymers: Synthesis and characterization

  摘要：

  Suzuki polycondensation (SPC) as an alternative strategy has been utilized for the first time to readily yield functional perfluorocyclobutyl (PFCB) aryl ether polymers, which are difficult to obtain via the traditional [2+2] thermal cyclopolymerization strategy. Using two reactive PFCB aryl ether molecules as monomers, the biphenyl PFCB aryl ether polymer without any functionality was first prepared and exhibited good thermal stability, up to 450 degrees C at 8% weight loss (N-2). By choosing appropriate functional monomers, aldehyde-functionalized PFCB aryl ether polymer precursor was also successfully prepared. Post-polymerization modification of this polymer precursor via Knoevenagel condensation yielded three distinct PFCB aryl ether polymers containing thermally stable triarylamine-based electro-optic chromophores. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.10.004

文献信息

• 聚(三苯胺-芴)染料及其应用
  申请人：中南大学

  公开号：CN103980731B

  公开（公告）日：2016-06-08

  本发明公开了聚(三苯胺-芴)染料及其应用，该聚(三苯胺-芴)染料是由具有三苯胺结构和具有芴结构的单体通过Stille偶联反应制成，制得的聚(三苯胺-芴)染料具有三苯胺和芴复合给体单元结构，将其应用于染料敏化太阳能电池的制备，可获得大电流密度、高光电转化率染料敏化太阳能电池。
• Reaction-based probe for hydrogen sulfite: dual-channel and good ratiometric response
  作者：Xiaohong Cheng、Ping He、Zhicheng Zhong、Guijie Liang

  DOI：10.1002/bio.3117

  日期：2016.11

  backbone with aldehyde group as the electron acceptor. Based on the nucleophilic addition reaction between hydrogen sulfite and aldehyde, all compounds could act as ratiometric optical probe for hydrogen sulfite and displayed efficient chromogenic and fluorogenic signaling. Upon the addition of hydrogen sulfite anions, probe T3 displayed apparent fluorescent color changes from yellowish‐green to blue, with

  我们设计并合成了一系列新的分子内电荷转移（ICT）分子（化合物T1，T2和T3），方法是将各种给电子噻吩基团与醛基作为电子受体的三苯胺骨架相连。基于亚硫酸氢与醛之间的亲核加成反应，所有化合物均可作为亚硫酸氢的配比光学探针，并显示出有效的发色和发荧光信号。添加亚硫酸氢根阴离子后，探针T3表现出明显的荧光颜色变化，从黄绿色变为蓝色，并具有较大的发射波长偏移（Δλ= 120 nm）。T3以高灵敏度响应亚硫酸氢盐，并且检测限被确定为低至0.9μM。同时，还可以观察到紫外可见光谱的明显变化。由于与醛的特殊亲核加成反应，T3相对于其他阴离子显示出高选择性。版权所有©2016 John Wiley＆Sons，Ltd.
• Development of New Conjugated Polymers with Donor−π-Bridge−Acceptor Side Chains for High Performance Solar Cells
  作者：Fei Huang、Kung-Shih Chen、Hin-Lap Yip、Steven K. Hau、Orb Acton、Yong Zhang、Jingdong Luo、Alex K.-Y. Jen

  DOI：10.1021/ja9066139

  日期：2009.10.7

  Two new conjugated polymers have been designed and synthesized for polymer solar cells. Both of them exhibit excellent photovoltaic properties with a power conversion efficiency as high as 4.74%. Different from the traditional linear donor-acceptor (D-A) type conjugated polymers, these newly designed polymers have a two-dimensional conjugated structure with their tunable acceptors located at the end of D-A side chains and connected with the donors on the main chain through an efficient in-bridge. This approach provides great flexibility in fine-tuning the absorption spectra and energy levels of the resultant polymers for achieving high device performance.
• Suzuki polycondensation and post-polymerization modification toward electro-optic perfluorocyclobutyl (PFCB) aryl ether polymers: Synthesis and characterization
  作者：Jingbo Wu、Benjamin R. Lund、Benjamin Batchelor、Daniel K. Dei、Shawna M. Liff、Dennis W. Smith

  DOI：10.1016/j.jfluchem.2015.10.004

  日期：2015.12

  Suzuki polycondensation (SPC) as an alternative strategy has been utilized for the first time to readily yield functional perfluorocyclobutyl (PFCB) aryl ether polymers, which are difficult to obtain via the traditional [2+2] thermal cyclopolymerization strategy. Using two reactive PFCB aryl ether molecules as monomers, the biphenyl PFCB aryl ether polymer without any functionality was first prepared and exhibited good thermal stability, up to 450 degrees C at 8% weight loss (N-2). By choosing appropriate functional monomers, aldehyde-functionalized PFCB aryl ether polymer precursor was also successfully prepared. Post-polymerization modification of this polymer precursor via Knoevenagel condensation yielded three distinct PFCB aryl ether polymers containing thermally stable triarylamine-based electro-optic chromophores. (C) 2015 Elsevier B.V. All rights reserved.
• Fluorescent and Colorimetric Probes for Mercury(II): Tunable Structures of Electron Donor and π-Conjugated Bridge
  作者：Xiaohong Cheng、Shuang Li、Huizhen Jia、Aoshu Zhong、Cheng Zhong、Jun Feng、Jingui Qin、Zhen Li

  DOI：10.1002/chem.201102376

  日期：2012.2.6

  1, 2, and 3) were synthesized by attaching various electron‐donating thiophenes groups to a triphenylamine backbone with an aldehyde group as the electron acceptor. Based on the protection reaction between ethanethiol and aldehyde, the corresponding dithioacetals (compounds S1, S2, and S3) were prepared to serve as novel colorimetric and fluorescent chemosensors for Hg2+ ions. Also, compound S1 was

  一系列新的分子内电荷转移（ICT）分子（化合物1，2，和3）通过各种供电子基团的噻吩附连到三苯胺骨架与醛基作为电子受体进行合成。基于乙硫醇与醛之间的保护反应，制备了相应的二硫缩醛（化合物S1，S2和S3），用作Hg 2+离子的新型比色和荧光化学传感器。此外，化合物S1还用于构建针对Hg 2+的基于化学反应的共轭聚合物探针（PS1）离子。在低至10 n M Hg 2+的存在下，化合物PS1的荧光强度出现明显变化。依赖于时间的DFT计算证实了传感过程是由ICT介导的。此外，化合物S1已成功应用于比例成像荧光法检测HeLa细胞中Hg 2+的显微成像。