5-[N,N-di(2-picolyl)amino]-4,4-difluoro-3-[4-(ethynyl)phenylethynyl]-8-(p-tolyl)-4-bora-3a,4a-diaza-s-indacene | 1251539-99-7

• 英文名称: 5-[N,N-di(2-picolyl)amino]-4,4-difluoro-3-[4-(ethynyl)phenylethynyl]-8-(p-tolyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 5-N,N-bis(2-picolyl)amino-4,4-difluoro-3-(4-(ethynyl)phenylethynyl)-8-(4-tolyl)-4-bora-3a,4adiaza-s-indacene
• CAS: 1251539-99-7
• 化学式: C₃₈H₂₈BF₂N₅
• 分子量: 603.482
• InChiKey: GBXJSAMOSGAKHS-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

• 作为反应物：
  描述：

  5-[N,N-di(2-picolyl)amino]-4,4-difluoro-3-[4-(ethynyl)phenylethynyl]-8-(p-tolyl)-4-bora-3a,4a-diaza-s-indacene 、 1,4-二(十二烷氧基)-2,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以48%的产率得到1,4-bis((4-((5-N,N-bis(2-picolyl)amino-4,4-difluoro)-8-(4-tolyl)-4-bora-3a,4a- diaza-s-indacen-3-yl)ethynyl)phenylethynyl)-2,5-bis(dodecyloxy)benzene
  参考文献：
  名称：

  The synthesis and spectroscopic characterization of poly(p-phenylene ethynylene) with 3-connected BODIPY end groups

  摘要：

  A novel 3-connected BODIPY end-capped poly(p-phenylene ethynylene) and a matching model compound were synthesized by palladium-catalyzed cross-coupling reaction The structures were confirmed using (1)H NMR UV-vis spectrophotometry and fluorescence spectroscopy Both the polymer and the model compound showed absorption and emission bands characteristic for the BODIPY chromophore and the p-phenylene ethynylene linker However while upon excitation of the p-phenylene ethynylene linker energy transfer occurs for nearly 100% in the model compound it is only a minor decay channel of the singlet excited state of the p-phenylene ethynylene linker in the polymer (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.dyepig.2010.08.006

文献信息

• Oligo(p-phenylene ethynylene)-BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum-Chemical Calculations
  作者：Shouchun Yin、Volker Leen、Carine Jackers、David Beljonne、Bernard Van Averbeke、Mark Van der Auweraer、Noël Boens、Wim Dehaen

  DOI：10.1002/chem.201100454

  日期：2011.11.18

  ethynylene)–BODIPY (OPEB) cassettes are reported. A series of oligo(p‐phenylene ethynylene)s (OPEs) with different conjugated chain lengths as energy donor subunit in the energy‐transfer system were capped at both ends with BODIPY chromophores as energy‐acceptor subunits. The effect of the conjugated chain of OPEs on energy transfer in the OPEB cassettes was investigated by UV/Vis and fluorescence spectroscopy

  报道了一系列低聚对苯撑乙炔-BODIPY（OPEB）盒的合成和能量转移特性。一系列具有不同共轭链长的低聚对苯乙炔（OPE）作为能量转移系统中的能量供体亚基，其两端均被BODIPY发色团作为能量受体亚基。通过紫外/可见光，荧光光谱和建模研究了OPE的共轭链对OPEB盒中能量转移的影响。随着n苯基乙炔单元数量的增加（n = 1–7），OPE n的最大吸收和发射红移。在OPEB n类似物中，分配给BODIPY部分的最大吸收量与OPE间隔基的长度无关。然而，当苯基乙炔单元的数目增加时，BODIPY带的相对吸收强度降低。OPEB n的发射光谱以在613 nm处的峰峰值为主，这与BODIPY部分的发射相对应，无论激发是在420 nm还是在550 nm处。此外，观察到非常小的谱带，其最大值在450和500 nm之间，并且其强度相对于BODIPY发射的强度随n的增加而增加，即OPE的激发态通过将能量转移至BODIPY部分，可有效地淬灭OPEB