2-bromobenzo[b]phosphole P-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromobenzo[b]phosphole P-oxide
• 英文别名: 2-bromo-1-phenylbenzo[b]phosphole P-oxide；2-Bromo-1-phenylphosphindole 1-oxide
• 化学式: C₁₄H₁₀BrOP
• 分子量: 305.111
• InChiKey: ZSZDMYWEQAZTRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromobenzo[b]phosphole P-oxide 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 74.0h， 生成 2-(1,3-Benzothiazol-2-yl)-1-phenylphosphindole 1-oxide
  参考文献：
  名称：

  Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using Palladium-Catalyzed Cross-Coupling Reactions

  摘要：

  Heck, Stille, and Sonogashira reactions of 2-bromobenzo[b]phosphole P-oxide afforded a series of 2-alkenyl- and 2-alkynyl-benzo[b]phosphole P-oxides. The charge-transfer character of the new benzo[b]phosphole pi-systems in the excited state is enhanced by the terminal electron-donating substituents. Furthermore, the C-Sn cross-coupling of the bromide was applied to the facile synthesis of a new Stille-coupling precursor, 2-stannylbenzo[b]phosphole.

  DOI：

  10.1021/ol401994e
• 作为产物：
  描述：

  1-phenylphosphindole 1-oxide 在 溴 、 三乙胺 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 2-bromobenzo[b]phosphole P-oxide
  参考文献：
  名称：

  Nief, Francois; Charrier, Claude; Mathey, Francois, Phosphorus and Sulfur and the Related Elements, 1982, vol. 13, p. 259 - 268

  摘要：

  DOI：

文献信息

• Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[<i>b</i>]phosphole oxide <i>via</i> PO-directed lithiation
  作者：Ayana Wakatsuki、Mariko Yukimoto、Mao Minoura、Kaori Fujii、Yoshifumi Kimura、Yoshihiro Matano

  DOI：10.1039/c8dt01503a

  日期：——

  Various 7-substituted benzo[b]phosphole derivatives were prepared by PO-directed lithiation of 1,2,3-triphenylbenzo[b]phosphole P-oxide and subsequent iodination and cross-coupling reactions. The electron-donating groups introduced at the 7-position produced dramatic solvatofluorochromism owing to the strong charge-transfer character of the excited state of the entire π-system.

  通过1,2,3-三苯基苯并[ b ]磷的P-氧化物的P O定向锂化以及随后的碘化和交叉偶联反应，制备了各种7-取代的苯并[ b ]磷的衍生物。由于整个π系统的激发态具有很强的电荷转移特性，在7位引入的给电子基团产生了剧烈的溶剂化氟致变色现象。
• 基于刚性氧膦基团的蓝光-绿光热延迟荧光材料
  申请人：西安交通大学

  公开号：CN109836460A

  公开（公告）日：2019-06-04

  基于刚性氧膦基团的蓝光‑绿光热延迟荧光材料，其具有式(I)所示的结构：本发明所公开的刚性氧膦基团的蓝光‑绿光TADF材料具有非常好的蓝光或绿光的色纯度、非常高的发光量子效率以及电荷注入/传输性能，适合作为发光材料制备高性能有机电致发光器件；另外，该类蓝光材料也具有很高的激发态能级，可以作为主体材料用于制备高性能有机电致发光器件。
• PHOSPHOLE COMPOUND AND FLUORESCENT DYE CONTAINING THE SAME
  申请人：NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY

  公开号：US20160333037A1

  公开（公告）日：2016-11-17

  The following formula is an example of a phosphole compound of the present invention. The phosphole compound of the present invention has the characteristic of maintaining a high fluorescence quantum yield in a wide range of solvents from low-polarity solvents to high-polarity solvents, as well as the characteristic in which the fluorescence wavelength shifts to the longer wavelength side as the polarity of the solvent increases. Because of these characteristics, the phosphole compound of the present invention is expected to be used, for example, for quantitatively determining the polarity in the environment therearound by using the absorption wavelength and fluorescence wavelength thereof, or used as a new fluorescent probe dye or a highly efficient luminescent material in organic electronic devices.

  以下公式是本发明的一种膦烯化合物的示例。本发明的膦烯化合物具有在从低极性溶剂到高极性溶剂的广泛范围内保持高荧光量子产率的特性，以及随着溶剂极性增加，荧光波长向较长波长侧移动的特性。由于这些特性，本发明的膦烯化合物预计可用于例如通过使用其吸收波长和荧光波长来定量确定其周围环境的极性，或者用作新的荧光探针染料或在有机电子器件中作为高效发光材料。
• π-Conjugated Molecules Containing Tetrathiafulvalene and Benzo[<i>b</i>]phosphole Oxide: Synthesis, Structure, and Electrochemical and Optical Properties
  作者：Shunki Ikeda、Aya Yoshimura、Takashi Shirahata、Yoshihiro Matano、Yohji Misaki

  DOI：10.1246/cl.210218

  日期：2021.8.5

  Three new π-conjugated molecules containing a tetrathiafulvalene (TTF) unit and a benzo[b]phosphole oxide unit were successfully synthesized. X-ray structual analysis revealed that the benzo[b]phosphole oxide unit exhibits high planarity, whereas the TTF unit adopts a bending structure. Electrochemical analysis by cyclic voltammetry revealed two pairs of redox waves derived from the TTF site. The absorption

  成功合成了三个含有四硫富瓦烯（TTF）单元和苯并[ b ]磷氧化物单元的新型π共轭分子。X射线结构分析表明，苯并[ b ]磷氧化物单元表现出高平面度，而TTF单元采用弯曲结构。循环伏安法的电化学分析揭示了来自 TTF 位点的两对氧化还原波。吸收带与 TTF 和苯并[ b ]磷氧化物部分的吸收带几乎相同，尽管它们的荧光被分子内电子转移显着淬灭。
• Synthesis and Structure-Property Relationships of 2,2′-Bis(benzo[<i>b</i>]phosphole) and 2,2′-Benzo[<i>b</i>]phosphole-Benzo[<i>b</i>]heterole Hybrid π Systems
  作者：Yukiko Hayashi、Yoshihiro Matano、Kayo Suda、Yoshifumi Kimura、Yoshihide Nakao、Hiroshi Imahori

  DOI：10.1002/chem.201203047

  日期：2012.12.7

  2′‐benzo[b]phosphole–benzo[b]heterole hybrid π systems is reported. 2‐Bromobenzo[b]phosphole P‐oxide underwent copper‐assisted homocoupling (Ullmann coupling) and palladium‐catalyzed cross‐coupling (Stille coupling) to give new classes of benzo[b]phosphole derivatives. The benzo[b]phosphole–benzo[b]thiophene and ‐indole derivatives were further converted to P,X‐bridged terphenylenes (X=S, N) by a palladium‐catalyzed

  首次对2,2'-双（苯并[ b ]磷脂）和2,2'-苯并[ b ]磷脂-苯并[ b ]杂原子杂化π系统的合成及其结构与性质的关系进行了首次综合研究。2-溴-苯并[ b ]磷杂环P氧化物后行铜辅助自偶联（Ullmann偶联）和钯-催化的交叉偶联（Stille偶联），得到苯并新类[ b ]磷杂环衍生物。所述苯并[ b ]磷杂-苯并[ b ]噻吩和吲哚衍生物进一步通过用4-辛炔通过C钯催化氧化环加成反应而转化为P，X桥连terphenylenes（X = S，N）β H激活。对三种化合物的X射线分析表明，由于通过CC键间的有效共轭作用，苯并[ b ]磷脂-苯并[ b ]杂环衍生物具有共面π平面。双（苯并[ b ]磷脂）P-氧化物的顺式和反式异构体的π-π*跃迁能和氧化还原电位非常接近，表明它们的光学和电化学性质几乎不受相对立体化学的影响。两个磷原子。苯并[ b ]磷-苯并[ b ]杂杂化物的光学性质高度依赖于苯并[