(E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline | 1016164-01-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline
• 英文别名: 2-{(E)-2-[4-(diphenylamino)phenyl]vinyl}benzothiazole；4-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-N,N-diphenylaniline
• CAS: 1016164-01-4
• 化学式: C₂₇H₂₀N₂S
• 分子量: 404.535
• InChiKey: AEZMCBLZCAYKFF-LVZFUZTISA-N

物化性质

• 熔点：
  155 °C (decomp)
• 沸点：
  601.4±58.0 °C(predicted)
• 密度：
  1.261±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基苯并噻唑 、 4-二苯胺基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以98%的产率得到(E)-N-{4-[2-(benzothiazol-2-yl)vinyl]phenyl}-N-phenylaniline
  参考文献：
  名称：

  Synthesis and Study of Novel Benzothiazole Derivatives with Potential Nonlinear Optical Properties

  摘要：

  描述了合成新的苯并噻唑推-拉系统作为NLO荧光团的候选物。对所制备化合物进行了光谱（UV/VIS和溶剂致色性）和理论研究（基于半经验AM1和PM3方法的电子性质）。研究了影响推-拉性质和分子内电荷转移（ICT）的结构和物理化学参数，并预测了具有增强高极化率β的化合物。与相应的中性苯并噻唑相比，苯并噻唑盐在NLO荧光团中表现出更高的效果。4-NPh2基团是最有效的给体。共轭桥的延伸改善了研究的NLO特性。附加的受体基团与杂环相结合导致了λmax的红移，但并不增加高极化率。

  DOI：

  10.1135/cccc20071069

文献信息

• Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption
  作者：Rémy Lartia、Clémence Allain、Guillaume Bordeau、Falk Schmidt、Céline Fiorini-Debuisschert、Fabrice Charra、Marie-Paule Teulade-Fichou

  DOI：10.1021/jo702002y

  日期：2008.3.1

  [Graphics]A versatile synthetic strategy to access a set of highly fluorescent g-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole JP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.