5,5-difluoro-3-phenyl-5H-5l4-imidazo[1',2':3,4][1,3,2]diazaborolo[1,5-a]pyridin-6-ium | 1379794-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,5-difluoro-3-phenyl-5H-5l4-imidazo[1',2':3,4][1,3,2]diazaborolo[1,5-a]pyridin-6-ium
• CAS: 1379794-46-3
• 化学式: C₁₄H₁₀BF₂N₃
• 分子量: 269.061
• InChiKey: ZXAMWHUQHPSVIK-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：

  5,5-difluoro-3-phenyl-5H-5l4-imidazo[1',2':3,4][1,3,2]diazaborolo[1,5-a]pyridin-6-ium 、 罗丹明B 以 氯仿 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  固体发射罗丹明：固态下氢键辅助的高效分子间荧光共振能量转移

  摘要：

  固体发射罗丹明配合物是通过将商业罗丹明 B (RhB) 与最近开发的固体发射硼 2-(2'-吡啶基)咪唑 (BOPIM) 衍生物混合而获得的。RhB 和 BOPIM 染料之间分子间氢键的形成在 RhB 的固态发射中起着关键作用。BOPIM 染料发射的消失表明发生了有效的分子间荧光共振能量转移 (FRET)。氢键还有助于防止 RhB 上的羧基部分之间的分子间相互作用，以减轻浓度诱导的荧光猝灭，因为复合物的发射可以通过在 RhB 吸收 (510 nm) 处的激发直接点亮。

  DOI：

  10.1080/10610278.2013.826807
• 作为产物：
  描述：

  2-(5-Phenyl-1H-imidazol-2-yl)-pyridine 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5,5-difluoro-3-phenyl-5H-5l4-imidazo[1',2':3,4][1,3,2]diazaborolo[1,5-a]pyridin-6-ium
  参考文献：
  名称：

  Solid-emissive boron–fluorine derivatives with large Stokes shift

  摘要：

  Novel BOPIM (boron 2-(2'-pyridyl)imidazole complex) derivatives with large Stokes shift were efficiently synthesized through two-step reactions, starting from commercially available 2-pyridinecarboxaldehyde and alpha-diketone. The dyes exhibit high fluorescent intensity in solution and also in solid state due to the intermolecular non-planar interactions. According to X-ray single crystal measurements, the non-covalent interactions (such as C-H center dot center dot center dot F-B, etc.) play important role in inhibiting planar pi-pi stacking, and the existence of terminal phenyl rings increases the electronic density of pi system, which facilitates the charge transfer from the electron-donating pi system to the electron-accepting boron moiety. DFT calculation based on X-ray crystallographic analysis was carried out for compound 2, giving consistent results with photophysical measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.052

文献信息

• Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state
  作者：Qifei Lin、Shuzhang Xiao、Ruohan Li、Ronghua Tan、Sa Wang、Ronghua Zhang

  DOI：10.1016/j.dyepig.2014.11.001

  日期：2015.3

  between photochromic diarylethenes and solid-emissive Boron–Fluorine dye. Photochromism of the self-assemblies results in slight modulation of the Boron–Fluorine dye's fluorescence in dilute solution, but high-contrast ON/OFF fluorescence switching in nanoparticles and in the solid state. During this process, intermolecular hydrogen bonds between the carboxyl units on diarylethenes and the imidazole ring

  我们描述了一种基于光致变色二硫醚和固体发射性硼-氟染料之间自组装复合物的实现荧光调制的简便方法。自组装体的光致变色作用导致在稀溶液中硼-氟染料的荧光发生轻微调节，但在纳米颗粒和固态时则进行高对比度的ON / OFF荧光转换。在此过程中，二芳硫醚上的羧基单元与硼氟荧光染料上的咪唑环之间的分子间氢键在从硼氟荧光染料到二芳硫醚的封闭异构体的有效荧光共振能量转移中起着重要作用。自组装复合物的激发波长（405 nm）几乎不引起二芳基乙烯分子的光致变色，提供无损读出能力。
• Solid-emissive boron–fluorine derivatives with large Stokes shift
  作者：Miaofu Mao、Shuzhang Xiao、Jianfeng Li、Ying Zou、Ronghua Zhang、Jiarong Pan、Feijun Dan、Kun Zou、Tao Yi

  DOI：10.1016/j.tet.2012.04.052

  日期：2012.6

  Novel BOPIM (boron 2-(2'-pyridyl)imidazole complex) derivatives with large Stokes shift were efficiently synthesized through two-step reactions, starting from commercially available 2-pyridinecarboxaldehyde and alpha-diketone. The dyes exhibit high fluorescent intensity in solution and also in solid state due to the intermolecular non-planar interactions. According to X-ray single crystal measurements, the non-covalent interactions (such as C-H center dot center dot center dot F-B, etc.) play important role in inhibiting planar pi-pi stacking, and the existence of terminal phenyl rings increases the electronic density of pi system, which facilitates the charge transfer from the electron-donating pi system to the electron-accepting boron moiety. DFT calculation based on X-ray crystallographic analysis was carried out for compound 2, giving consistent results with photophysical measurements. (C) 2012 Elsevier Ltd. All rights reserved.
• Solid-emissive rhodamine: hydrogen bonding-assisted efficient intermolecular fluorescence resonance energy transfer in the solid state
  作者：Qiong Cao、Shuzhang Xiao、Ruohan Li、Qifei Lin、Changying Yang、Kun Zou、Feijun Dan

  DOI：10.1080/10610278.2013.826807

  日期：2014.2.1

  fluorescence resonance energy transfer (FRET). The hydrogen bond also helps prevent the intermolecular interaction between the carboxyl moieties on RhB to alleviate concentration-induced fluorescence quenching because the emission of the complexes can be directly lightened by excitation at the RhB absorption (510 nm). Our results indicate that intermolecular FRET assisted by non-covalent interactions can

  固体发射罗丹明配合物是通过将商业罗丹明 B (RhB) 与最近开发的固体发射硼 2-(2'-吡啶基)咪唑 (BOPIM) 衍生物混合而获得的。RhB 和 BOPIM 染料之间分子间氢键的形成在 RhB 的固态发射中起着关键作用。BOPIM 染料发射的消失表明发生了有效的分子间荧光共振能量转移 (FRET)。氢键还有助于防止 RhB 上的羧基部分之间的分子间相互作用，以减轻浓度诱导的荧光猝灭，因为复合物的发射可以通过在 RhB 吸收 (510 nm) 处的激发直接点亮。