meso-(p-trimethylsilylphenyl)-BODIPY | 1564225-94-0

• 英文名称: meso-(p-trimethylsilylphenyl)-BODIPY
• CAS: 1564225-94-0
• 化学式: C₁₈H₁₉BF₂N₂Si
• 分子量: 340.256
• InChiKey: VEKUOARCZXCMTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  2-((4-(trimethylsilyl)phenyl)(1H-pyrrol-2-yl)methyl)-1H-pyrrole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 11.0h， 以28%的产率得到meso-(p-trimethylsilylphenyl)-BODIPY
  参考文献：
  名称：

  Effect of substituent position on optical properties of boron-dipyrromethane isomers

  摘要：

  Three isomeric meso-SiMe3C6H4 substituted BODIPYs have been synthesized and their optical properties studied. The constitutional isomers show similar absorption properties but vastly different emissive properties as a result of their different conformational flexibility. Fluorine-19 NMR study is used to unravel the conformational state of the BODIPY isomers at a molecular level. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.11.032

文献信息

• Scope and Limitations of the Liebeskind–Srogl Cross-Coupling Reactions Involving the Biellmann BODIPY
  作者：Lourdes Betancourt-Mendiola、Ismael Valois-Escamilla、Teresa Arbeloa、Jorge Bañuelos、Iñigo López Arbeloa、Juan O. Flores-Rizo、Rongrong Hu、Erik Lager、César F. A. Gómez-Durán、José L. Belmonte-Vázquez、Mayra R. Martínez-González、Ismael J. Arroyo、Carlos A. Osorio-Martínez、Enrique Alvarado-Martínez、Arlette Urías-Benavides、Brenda D. Gutiérrez-Ramos、Ben Zhong Tang、Eduardo Peña-Cabrera

  DOI：10.1021/acs.joc.5b00731

  日期：2015.6.5

  Several new examples of meso-(het)aryIBODIPY were prepared via the Liebeskind-Srogl (L-S) cross-coupling reaction of the Biellmann BODIPYs (1a,b) and aryl- and heteroarylboronic acids in good to excellent yield. It was shown that this reaction could be carried out under microwave heating to shorten reaction times and/or increase the yield. It was illustrated that organostannanes also participate in the L-S reaction to give the corresponding BODIPY analogues in short reaction times and also with good to excellent yields. We analyze the role of the substituent at the sensitive meso position in the photophysical signatures of these compounds. In particular, the rotational motion of the aryl ring and the electron donor ability of the anchored moieties rule the nonradiative pathways and, hence, have a deep impact in the fluorescence efficiency.