7,7-Difluoro-4,5-diphenyl-3,6-diaza-8-azonia-7-boranuidatricyclo[6.4.0.02,6]dodeca-1(12),2,4,8,10-pentaene | 1379794-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7,7-Difluoro-4,5-diphenyl-3,6-diaza-8-azonia-7-boranuidatricyclo[6.4.0.02,6]dodeca-1(12),2,4,8,10-pentaene
• 英文别名: 7,7-difluoro-4,5-diphenyl-3,6-diaza-8-azonia-7-boranuidatricyclo[6.4.0.02,6]dodeca-1(12),2,4,8,10-pentaene
• CAS: 1379794-47-4
• 化学式: C₂₀H₁₄BF₂N₃
• 分子量: 345.159
• InChiKey: BHYVFODRPYOXNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,7-Difluoro-4,5-diphenyl-3,6-diaza-8-azonia-7-boranuidatricyclo[6.4.0.02,6]dodeca-1(12),2,4,8,10-pentaene 、 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-(4,5-diphenyl-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， 以32%的产率得到7,7-Difluoro-4,5-diphenyl-3,6-diaza-8-azonia-7-boranuidatricyclo[6.4.0.02,6]dodeca-1(12),2,4,8,10-pentaene
  参考文献：
  名称：

  具有光动力学活性的非聚集硼氟衍生物

  摘要：

  可以轻松合成和表征具有大斯托克斯位移的新型非聚集硼氟衍生物。这些染料显示出中等的吸收系数和强烈的荧光发射，并且在溶剂和固态下均具有出色的光稳定性。根据X射线单晶分析，非共价分子间相互作用可提供刚性结构，从而抑制聚集体形成。这些非聚集的染料在光照射下会产生单线态氧，这使其成为光动力疗法的理想候选者。版权所有©2012 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.2914

文献信息

• Synthesis, structures and photophysical properties of boron–fluorine derivatives based on pyridine/1,8-naphthyridine
  作者：Zhensheng Li、Xiaojun Lv、Yong Chen、Wen-Fu Fu

  DOI：10.1016/j.dyepig.2014.01.022

  日期：2014.6

  Three boron fluorine complexes B1-B3 containing pyridine/1,8-naphthyridine were synthesized and structurally characterized. Compounds B1 and B2 exhibited strong fluorescence in solution and solid state. The solvent-dependent luminous properties and large Stokes shift in solution could be explained by intramolecular charge transfer, which is confirmed by time-dependent density functional theory calculation. The absolute quantum yield of B1 in powder form reached 0.48 because of inhibiting planar pi...pi stacking. Single-crystal X-ray diffraction analyses of B1 and B2 revealed that weak intermolecular C H...F and H...pi interactions hinder further stacking of pi...pi dimers, consequently preventing aggregation-induced quenching. Complex 113, composed of boron-dipyrromethene and 1,8-naphthyridine fluorophore, had potential applications as a pH ratiometric fluorescent sensor. (c) 2014 Elsevier Ltd. All rights reserved.
• 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.
• Structure–property correlation of solid-emissive boron–fluorine derivatives
  作者：Qiong Cao、Shuzhang Xiao、Miaofu Mao、Xiaohong Chen、Sa Wang、Ling Li、Kun Zou

  DOI：10.1016/j.jorganchem.2012.07.043

  日期：2012.10

  A series of solid-emissive BOPIM (boron 2-(2-pyridyl)imidazole complex) dyes, bearing electron-donating or -withdrawing substituents (methoxy, hydrogen, or nitro), are facilely synthesized. The compounds were characterized by H-1 NMR, C-13 NMR and MS. X-ray single crystal diffractions of BOPIM 1 and 2 indicate that nonplanar rigid structures were formed through intermolecular non-covalent interactions. Due to these non-covalent interactions, these dyes exhibit intense fluorescence in solution and also in solid state. According to H-1 NMR analysis, electronic effect of the substitutes plays an important role in contribution to these BOPIMs' electronic states. The photophysical measurements reveal that electron-donating groups (methoxy) lead to significant bathochromism of the absorption and emission. In contrast, electron-withdrawing moieties (nitro) play the reverse role. However, BOPIM 3 bearing nitro groups emits long wavelength fluorescence in solid state, probably due to the formation of intermolecular hydrogen bond. This work elucidates the spectroscopic structure-property relationship of solid-emissive BOPIMs, which would be valuable for design of solid-emissive dyes. (C) 2012 Elsevier B. V. All rights reserved.