N,N'-dibutylboryl-5-phenyldipyrrin | 870753-31-4

• 英文名称: N,N'-dibutylboryl-5-phenyldipyrrin
• CAS: 870753-31-4
• 化学式: C₂₃H₂₉BN₂
• 分子量: 344.308
• InChiKey: PTOGAJCEWISUDS-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：

  三氟甲磺酸二丁硼 、 5-苯基联吡咯甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N,N'-dibutylboryl-5-phenyldipyrrin
  参考文献：
  名称：

  Boron complexation strategy for use in manipulating 1-acyldipyrromethanes

  摘要：

  制备金属配合物的方法包括将1-单酰基二吡咯甲烷与化合物R1R2MX（其中M为硼，R1和R2分别为有机取代基；X为离子离去基团）结合，以产生配合物DMR1R2的金属配合物，其中DH为1-单酰基二吡咯甲烷。这些方法和配合物对于二吡咯甲烷和卟啉的纯化和合成是有用的。

  公开号：

  US20050282778A1

文献信息

• Structural Control of the Photodynamics of Boron−Dipyrrin Complexes
  作者：Hooi Ling Kee、Christine Kirmaier、Lianhe Yu、Patchanita Thamyongkit、W. Justin Youngblood、Matthew E. Calder、Lavoisier Ramos、Bruce C. Noll、David F. Bocian、W. Robert Scheidt、Robert R. Birge、Jonathan S. Lindsey、Dewey Holten

  DOI：10.1021/jp0525078

  日期：2005.11.1

  Boron-dipyrrin chromophores containing a 5-aryl group with or without internal steric hindrance toward aryl rotation have been synthesized and then characterized via X-ray diffraction, static and time-resolved optical spectroscopy, and theory. Compounds with a 5-phenyl or 5-(4-tert-butylphenyl) group show low fluorescence yields (similar to 0.06) and short excited-singlet-state lifetimes (similar to 500 ps), and decay primarily (> 90%) by nonradiative internal conversion to the ground state. In contrast, sterically hindered analogues having an o-tolyl or mesityl group at the 5-position exhibit high fluorescence yields (similar to 0.9) and long excited-state lifetimes (similar to 6 ns). The X-ray structures indicate that the phenyl or 4-tert-butylphenyl ring lies at an angle of similar to 60 degrees with respect to the dipyrrin framework whereas the angle is similar to 80 degrees for mesityl or o-tolyl groups. The calculated potential energy surface for the phenyl-substituted complex indicates that the excited state has a second, lower energy minimum in which the nonhindered aryl ring rotates closer to the mean plane of the dipyrrin, which itself undergoes some distortion. This relaxed, distorted excited-state conformation has low radiative probability as well as a reduced energy gap from the ground state supporting a favorable vibrational overlap factor for nonradiative deactivation. Such a distorted conformation is energetically inaccessible in a complex bearing the sterically hindered o-tolyl or mesityl group at the 5-position, leading to a high radiative probability involving conformations at or near the initial Franck-Condon form of the excited state. These combined results demonstrate the critical role of aryl-ring rotation in governing the excited-state dynamics of this class of widely used dyes.