9-bis(trimethylsilyl)amino-9-borafluorene | 1539305-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 9-bis(trimethylsilyl)amino-9-borafluorene
• 英文别名: (Me3Si)2NBFl；N,N-bis(trimethylsilyl)benzo[b][1]benzoborol-5-amine
• CAS: 1539305-73-1
• 化学式: C₁₈H₂₆BNSi₂
• 分子量: 323.393
• InChiKey: CHWSMKJOSHDWHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  9-bromo-9-borafluorene 以 甲苯 为溶剂， 反应 72.0h， 生成 9-bis(trimethylsilyl)amino-9-borafluorene
  参考文献：
  名称：

  Synthesis and Luminescent Properties of Lewis Base-Appended Borafluorenes

  摘要：

  A series of Lewis base adducts of 9-bromo-9-borafluorene (BrBFl-LB, LB = IPr, IPrCH2, PPh3, and PCy3), parent borafluorenes (HBFl-IPr and HBFl-IPrCH2), and the bisadduct [(DMAP)(2)BFl]Br were prepared and structurally characterized (IPr = [(HCNDipp)(2)C:], IPrCH2 = [(HCNDipp)(2)C=CH2], Dipp = 2,6-i-Pr2C6H3, and DMAP = N,N-dimethylaminopyridine). The adducts BrBFl-IPr, BrEFl-PPh3, BrBFl-PCy3, [(DMAP)(2)BFI]Br, BrBFl-IPrCH2, and HBFl-IPrCH2 were found to exhibit bright blue luminescence with low to moderately high quantum efficiencies (19 to 63%). Selective irradiation at different excitation wavelengths revealed the presence of two distinct emission processes in the adducts BrBFl-LB, leading to a ligand-independent, presumably borafluorene-based, blue light emission at 435 nm and another less intense emission band in the ultraviolet region (315-324 nm); [(DMAP)(2)BFl]Br exhibits an emission profile that tails into the visible region. Time-dependent density functional theory studies are also included for representative borafluorene adducts. With a judicious choice of functional groups at boron, one can envisage the future generation of a whole library of 4-coordinate borafluorene-based luminogens that complement the efficient light-emitting behavior known for the widely studied boron-dipyrromethene analogues.

  DOI：

  10.1021/ic402408t

文献信息

• Photo electron transfer induced desilylation of <i>N</i>,<i>N</i>-bis(trimethylsilyl)aminodibenzoborole to aminodibenzoborole
  作者：Constanze Keck、Cäcilia Maichle-Mössmer、Holger F. Bettinger

  DOI：10.1039/c9cc03415c

  日期：——

  The synthesis of 9-amino-9-borafluorene is described using a photoinduced twofold desilylation of the N,N-bis(trimethylsilyl) derivative 2. The mechanistic analysis suggests an initial single electron transfer step from 2 to the halogen containing solvent. 9-Amino-9-borafluorene undergoes a photoinduced cyclooligomerization, most reasonably to the dimer.

  使用光诱导的N，N-双（三甲基甲硅烷基）衍生物2的两倍去甲硅烷基化反应，描述了9-氨基-9-硼芴的合成。机理分析表明初始的单电子转移步骤是从2到含卤素的溶剂。9-氨基-9-硼芴经历了光诱导的环寡聚，最合理地是二聚体。