10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophene | 1263143-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophene
• 英文别名: 10-phenyl[1]benzophospholo[3,2-b][1]benzothiophene；10-phenylphosphindolo[3,2-b][1]benzothiophene；C14H8SPPh
• CAS: 1263143-04-9
• 化学式: C₂₀H₁₃PS
• 分子量: 316.363
• InChiKey: ZTUAOLDSNKVJOA-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophene 在 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(C14H8SPPh)BH3
  参考文献：
  名称：

  Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P−S System

  摘要：

  New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of the materials' properties by exploitation of the different reactivities between sulfur and phosphorus. P-31 NMR. spectroscopy and X-ray crystallographic studies revealed that the different electronic effects of the secondary heteroatom, sulfur, influence not only the conjugation in the heterotetracene core but also the behavior of the phosphorus center. UV-vis and fluorescence spectroscopy showed that the scaffold's band gap is mainly controlled by the electronic nature of sulfur, while the fluorescence quantum yield highly depends on the electronic nature of phosphorus. Cyclic voltammetry indicated that the redox properties of the system could be altered by selective modification of the respective heteroatom (oxidation of sulfur and/or functionalization of trivalent phosphorus). Importantly, oxidation of the phosphorus center results in enhanced reduction features of the heterotetracene system, and oxidation of the sulfur center further enhances the electron acceptor character of the core. Theoretical calculations provided insights on both selectivity of phosphorus chemistry and communication between the two heteroatoms (sulfur and phosphorus). Macroscopic self-organization of the heterotetracenes was observed when the tetracene core is functionalized with pendant functional groups. Preliminary results showed that extension of the molecule with an alkyl chain along the long axis of molecules induces the formation of ID microfibers, which was confirmed by fluorescence microscopy and scanning electron microscopy.

  DOI：

  10.1021/ja108081b
• 作为产物：
  描述：

  2-溴苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 溴 、 二乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.75h， 生成 10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophene
  参考文献：
  名称：

  含15和16族元素的苯并噻吩稠合的苯并杂杂环的一般合成，结构和光学性质

  摘要：

  通过通用方法合成了一系列含有第15组（N，P，As和Sb）和第16组（O，S，Se和Te）元素的苯并噻吩并[3,2- b ]苯并杂环。X射线分析表明，所有的四环杂并苯骨架都是平面的。与第15族-杂蒽相比，在第16族-杂蒽的激发能和它们的原子半径之间发现线性关系。进行密度泛函理论计算和电化学测量以了解结构与光学性质之间的关系。

  DOI：

  10.1016/j.tet.2016.10.048

文献信息

• External-Stimuli Responsive Photophysics and Liquid Crystal Properties of Self-Assembled “Phosphole-Lipids”
  作者：Yi Ren、Wang Hay Kan、Matthew A. Henderson、Paolo G. Bomben、Curtis P. Berlinguette、Venkataraman Thangadurai、Thomas Baumgartner

  DOI：10.1021/ja206784f

  日期：2011.10.26

  induce liquid crystalline and soft crystal phase behavior in the solid state, which was studied by differential scanning calorimetry (DSC), polarized optical microscopy (POM), and variable temperature powder X-ray diffraction (VT-PXRD). The studies revealed that both conjugated backbones and counteranions work together to organize the systems into different morphologies (liquid crystal/soft crystal). Dithieno[3

  合成了一系列结合磷的电子特征和脂质自组装特征的新型两亲性鏻材料。可变浓度/温度和 2D NMR 研究表明，系统在“封闭”和“开放”形式之间发生分子内构象变化，这是由分子间相互作用触发的。通过差示扫描量热法 (DSC)、偏光显微镜 (POM) 和变温粉末 X 射线衍射 (VT- PXRD）。研究表明，共轭骨架和反阴离子共同作用将系统组织成不同的形态（液晶/软晶体）。迪西诺[3, 由于聚集诱导增强发射 (AIEE)，2-b:2',3'-d] 磷基化合物在固态和低温溶液中表现出增强的发射。可以通过非融合系统主支架内的分子间电荷转移 (ICT) 过程有效抑制通过稠环系统中鏻中心的烷氧基苄基诱导的光致电子转移 (PET)，静态和动态荧光证实了这一点光谱学。这些新材料的动态特性还赋予系统外部刺激响应光物理特性，可以由温度和/或机械力触发。-d]磷基化合物在固态和低温溶液中由于聚集诱导增强发射（AIEE
• JP5780624
  申请人：——

  公开号：——

  公开（公告）日：——
• Ladder-Type <i>P</i>,<i>S</i>-Bridged <i>trans</i>-Stilbenes
  作者：Wannes Weymiens、Mark Zaal、J. Chris Slootweg、Andreas W. Ehlers、Koop Lammertsma

  DOI：10.1021/ic201116p

  日期：2011.9.5

  Phosphole-containing pi-systems have emerged as building blocks with enormous potential as electronic materials because of the tunability of the phosphorus center. Among these, asymmetric P-bridged trans-stilbenes are still rare, and here an elegant and efficient synthesis toward such fluorescent molecular frameworks is described. Fine-tuning of the photophysical properties is attempted by enforcing the planarization of the phosphorus tripod and thus increasing the interaction between the phosphorus lone pair and the pi-system, The electronic structure of the pi-conjugated frameworks is analyzed with NMR, UV-vis and fluorescence spectroscopy, and time-dependent density functional theory (TD-DFT) calculations.
• Structure–Property Studies Toward the Stimuli-Responsive Behavior of Benzyl–Phospholium Acenes
  作者：Yi Ren、Thomas Baumgartner

  DOI：10.1021/ic2026335

  日期：2012.2.20

  A series of new phospholium acenes, quaternized with benzyl groups, was synthesized. Both different pi-conjugated backbones and electron-donating/-withdrawing benzyl groups were systematically studied to reveal details on the nature of their structural dynamics. Extensive NMR studies (including variable concentration/temperature and 2D) suggested that the systems undergo intramolecular conformation changes in solution that are strongly affected by the electronic nature of the benzyl group, and thereby significantly affecting the phosphole-typical sigma*-pi* interaction. This class of "smart" phosphole system exhibits enhanced emission in the solid state and at low temperature in solution, due to aggregation-induced enhanced emission (AIEE). The dynamic features of these smart phospholes also endow the systems with external-stimuli (thermal and mechanical force) responsive photophysical properties. Crystallographic studies and theoretical calculations confirmed that the thermal response of the phospholium system is mainly clue to the conformation changes in solution, while the mechanical response of the system can be attributed to both the intramolecular conformation and the intermolecular organization changes in the solid state.