4,4-difluoro-8-(2-furyl)-3,5-bis(pyridin-3-yloxy)-4-bora-3a,4a-diaza-s-indacene | 1228186-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-difluoro-8-(2-furyl)-3,5-bis(pyridin-3-yloxy)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 2,2-Difluoro-8-(furan-2-yl)-4,12-dipyridin-3-yloxy-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1228186-27-3
• 化学式: C₂₃H₁₅BF₂N₄O₃
• 分子量: 444.205
• InChiKey: OTYRKGYNBQSNKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  zinc tetraphenylporphyrin 、 4,4-difluoro-8-(2-furyl)-3,5-bis(pyridin-3-yloxy)-4-bora-3a,4a-diaza-s-indacene 反应 0.5h， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of non-covalent BODIPY–metalloporphyrin dyads and triads

  摘要：

  Boron-dipyrromethenes (BODIPY) containing oxypyridine substituents at 3- and 3,5-positions and metalloporphyrins (Zn(II), Ru(II)) were used to synthesize four non-covalent BODIPY-metalloporphyrin dyads and four BODIPY-metalloporphyrin triads assembled using metal pyridine 'N' interaction. The formation of BODIPY-metalloporphyrin assemblies was confirmed by 1D and 2D NMR methods and X-ray crystal structure obtained for one of the BODIPY-metalloporphyrin dyad. In H-1 NMR, the signals of oxypyridine group(s) of BODIPY unit showed significant upfield shifts supporting the coordination of oxypyridine group of BODIPY unit to metalloporphyrin unit. The NMR study also indicated that Zn(II) porphyrin forms relatively weak BODIPY-Zn(II) porphyrin conjugates, whereas Ru(II) porphyrin forms strong BODIPY-Ru(II) porphyrin conjugates. The X-ray structure solved for BODIPY-Zn(II)porphyrin dyad revealed that the Zn(II) porphyrin coordinated to the BODIPY unit obliquely and the angle between the Zn(II) porphyrin and the pyridyl ring is 70 degrees. The absorption properties of stable BODIPY-Ru(II) porphyrin conjugates showed the overlapping absorption features of both the components and the fluorescence studies indicated that the BODIPY unit emission was significantly quenched on coordination with RuTPP(CO) unit. The electrochemical studies exhibited the features of both BODIPY and metalloporphyrin units in dyads and traids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.048
• 作为产物：
  描述：

  3-羟基吡啶 、 3,5-dibromo-4,4-difluoro-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以62%的产率得到4,4-difluoro-8-(2-furyl)-3,5-bis(pyridin-3-yloxy)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  3,5-双(氧代吡啶基)-和3,5-双(吡啶氧基)-取代的硼-二吡咯亚甲基的合成和光物理性质

  摘要：

  2-、3-和 4-羟基吡啶与 3,5-二溴内消旋芳基和内消旋呋喃基硼二吡咯亚甲基 (BODIPY) 的亲核取代反应导致形成相应的 3,5-双(氧代吡啶基)-BODIPY 和3,5-双-（吡啶基氧基）-BODIPY 的产率不错。作为溶剂的函数，研究了在 3 位和 5 位的吡啶酮与氧吡啶对光谱、电化学和光物理性质的影响。与 3,5-双（吡啶氧基）-BODIPY 相比，3,5-双（氧代吡啶基）-BODIPY 表现出广泛的红移吸收和发射带，降低了量子产率和寿命，显示出较大的斯托克斯位移和更容易还原。

  DOI：

  10.1002/ejoc.200901460

文献信息

• Synthesis and Photophysical Properties of 3,5-Bis(oxopyridinyl)- and 3,5-Bis(pyridinyloxy)-Substituted Boron-Dipyrromethenes
  作者：Tamanna K. Khan、M. Rajeswara Rao、M. Ravikanth

  DOI：10.1002/ejoc.200901460

  日期：2010.4

  meso-aryl and meso-furyl borondipyrromethenes (BODIPYs) resulted in the formation of the corresponding 3,5-bis(oxopyridinyl)-BODIPYs and 3,5-bis-(pyridinyloxy)-BODIPYs in decent yields. The effect of a pyridone versus an oxypyridine at the 3- and 5-positions on the spectral, electrochemical and photophysical properties were studied as a function of solvent. The 3,5-bis(oxopyridinyl)-BODIPYs exhibit broad, red-shifted

  2-、3-和 4-羟基吡啶与 3,5-二溴内消旋芳基和内消旋呋喃基硼二吡咯亚甲基 (BODIPY) 的亲核取代反应导致形成相应的 3,5-双(氧代吡啶基)-BODIPY 和3,5-双-（吡啶基氧基）-BODIPY 的产率不错。作为溶剂的函数，研究了在 3 位和 5 位的吡啶酮与氧吡啶对光谱、电化学和光物理性质的影响。与 3,5-双（吡啶氧基）-BODIPY 相比，3,5-双（氧代吡啶基）-BODIPY 表现出广泛的红移吸收和发射带，降低了量子产率和寿命，显示出较大的斯托克斯位移和更容易还原。
• Synthesis of non-covalent BODIPY–metalloporphyrin dyads and triads
  作者：Tamanna K. Khan、Mangalampalli Ravikanth

  DOI：10.1016/j.tet.2011.11.048

  日期：2012.1

  Boron-dipyrromethenes (BODIPY) containing oxypyridine substituents at 3- and 3,5-positions and metalloporphyrins (Zn(II), Ru(II)) were used to synthesize four non-covalent BODIPY-metalloporphyrin dyads and four BODIPY-metalloporphyrin triads assembled using metal pyridine 'N' interaction. The formation of BODIPY-metalloporphyrin assemblies was confirmed by 1D and 2D NMR methods and X-ray crystal structure obtained for one of the BODIPY-metalloporphyrin dyad. In H-1 NMR, the signals of oxypyridine group(s) of BODIPY unit showed significant upfield shifts supporting the coordination of oxypyridine group of BODIPY unit to metalloporphyrin unit. The NMR study also indicated that Zn(II) porphyrin forms relatively weak BODIPY-Zn(II) porphyrin conjugates, whereas Ru(II) porphyrin forms strong BODIPY-Ru(II) porphyrin conjugates. The X-ray structure solved for BODIPY-Zn(II)porphyrin dyad revealed that the Zn(II) porphyrin coordinated to the BODIPY unit obliquely and the angle between the Zn(II) porphyrin and the pyridyl ring is 70 degrees. The absorption properties of stable BODIPY-Ru(II) porphyrin conjugates showed the overlapping absorption features of both the components and the fluorescence studies indicated that the BODIPY unit emission was significantly quenched on coordination with RuTPP(CO) unit. The electrochemical studies exhibited the features of both BODIPY and metalloporphyrin units in dyads and traids. (C) 2011 Elsevier Ltd. All rights reserved.