4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene | 1296130-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(8-hydroxyquinoline)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene；4,4-difluoro-8-(8-hydroxyquinolin-5-yl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene；8-HOQ-BODIPY；5-(2,2-Difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)quinolin-8-ol
• CAS: 1296130-58-9
• 化学式: C₂₂H₂₀BF₂N₃O
• 分子量: 391.228
• InChiKey: KZGPKSPZWKUTST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 碘 、 碘酸 作用下， 以70%的产率得到8-(6-iodine-8-hydroxyquinoline)-4,4-difluoro-1,3,5,7-tetramethyl-2,6-diiodine-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  BODIPY-钴肟-抗坏血酸均相体系中酸性水溶液的光催化制氢

  摘要：

  摘要将在BODIPY核中介孔位具有8-羟基喹啉或苯胺部分的碘化硼二吡咯亚甲基（BODIPY）染料用作酸性水溶液中三组分光驱动H2系统的高效光敏剂（PSs）。与钴肟[CoIII（dmgH）2PyCl]（dmgH =二甲基乙二酰亚胺，py =吡啶）作为质子还原催化剂，抗坏血酸（H2A）作为牺牲电子给体。这是BODIPYs的第一个例子，它是在酸性水性条件下使用的均相制氢PS。它们在酸性溶液中有活性，而在碱性条件下没有活性，这可能表明存在分子内和分子间电子转移反应之间的竞争程度。PS和分子催化剂之间需要进行有效的双分子电子转移反应才能产生H2，而PS的分子内电子转移可能会抑制H2的产生。结果强调可以对BODIPYs进行化学修饰，从而允许酸和碱条件的转化以产生光驱动的H2。

  DOI：

  10.1016/j.cclet.2018.05.003
• 作为产物：
  描述：

  8-羟基喹啉 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  用于线粒体靶向红光光动力疗法的二溴-BODIPY-8-羟基喹啉钴(III)

  摘要：

  硼二吡咯亚甲基 (BODIPY) 染料的光物理特性使其适用于细胞成像和光动力疗法 (PDT)。这些染料的功效可以通过设计它们的二溴/二碘衍生物来增强。四齿N,N,N,O-供体聚吡啶基酚盐 ( HL ) 和二齿N,O-供体 8-羟基喹啉 ( HL 1 ) 及其 BODIPY ( HL 2 ) 或二溴-BODIPY ( HL ) 杂配 Co(III) 配合物3 ) 吊坠，[Co III (L)(L 1−3 )]X ( 1 – 3 ) （其中 X = ClO 4为1 , 2合成并研究了3的 Cl 和 Cl 。对二溴-BODIPY 配体HL 3进行了结构表征。二溴-BODIPY复合物3 的单线态氧量子产率 (ψ Δ ) 值为 ∼0.25，在红光 (600–720 nm) 照射下，在 HeLa 癌细胞中表现出显着的细胞凋亡光细胞毒性，给出半最大抑制浓度 (IC 50）值为0.36 μM（光细胞毒性指

  DOI：

  10.1016/j.poly.2023.116656

文献信息

• BODIPY chromophores as efficient green light sensitizers for lanthanide-induced near-infrared emission
  作者：Yihan Zhong、Liping Si、Hongshan He、Andrew G. Sykes

  DOI：10.1039/c1dt11137j

  日期：——

  A new boron dipyrromethene (BODIPY) modified 8-hydroxylquinoline ligand (8-HOQ-BODIPY) is synthesized for the sensitization of near-infrared emission of lanthanide(III) ions. The BODIPY unit, as revealed by single-crystal X-ray diffraction analysis, aligns almost perpendicularly to the 8-HOQ unit. The ligand exhibits strong absorption at ∼506 nm and fluorescence at 510 nm in organic solvents with quantum yields ranging from ∼0.45 in dichloromethane to 0.015 in ethanol. It forms stable ytterbium(III), erbium(III) and neodymium(III) complexes with 3 : 1 ligand-to-metal molar ratios. Upon excitation (∼522 nm), the neodymium(III) and erbium(III) complexes emit weakly at 1060 and 1382 nm, respectively, whereas the ytterbium(III) complex exhibits strong emission at 976 and 1003 nm. The results demonstrate the potential of BODIPY dyes as efficient and robust visible light sensitizers for lanthanide-based NIR emitters in medical diagnosis.

  我们合成了一种新的硼二吡咯烷（BODIPY）修饰的 8-羟基喹啉配体（8-HOQ-BODIPY），用于敏化镧系元素（III）离子的近红外发射。单晶 X 射线衍射分析表明，BODIPY 单元几乎垂直于 8-HOQ 单元。在有机溶剂中，配体在 506 纳米波长处有强吸收，在 510 纳米波长处有强荧光，量子产率从二氯甲烷中的 0.45 到乙醇中的 0.015 不等。它能形成稳定的镱（III）、铒（III）和钕（III）配合物，配体与金属之间的配位比为 3 ：1 的配体-金属摩尔比。在激发（522 纳米）时，钕（III）和铒（III）络合物分别在 1060 纳米和 1382 纳米处微弱发光，而镱（III）络合物则在 976 纳米和 1003 纳米处强烈发光。这些结果证明了 BODIPY 染料作为镧系近红外发射体的高效、稳健可见光敏化剂在医疗诊断中的潜力。
• 一种于极端pH条件下检测铜离子的荧光探针、制备方法及其应用
  申请人：山西农业大学

  公开号：CN113943316B

  公开（公告）日：2023-04-21

  本发明公开了一种于极端pH条件下检测铜离子的荧光探针、制备方法及其应用，制备方法为：将8‑羟基喹啉‑5‑醛BODIPY和1‑(6‑(氯甲基)吡啶‑2‑基)‑N,N‑二(吡啶‑2‑亚甲基)甲胺溶解于乙腈中，搅拌至溶解后加入碳酸钾，混合物加热至回流反应7～9小时，TLC监测反应进程，判断反应终止；反应结束后，反应液经过过滤、除溶剂，残留物用硅胶柱层析色谱分离纯化，即得。本发明提高了检测的专一性和稳定性，灵敏度高，抗干扰性强，适用的pH范围广，荧光探针同Cu2+作用前后溶液变化明显，裸眼识别效果好。
• The naphthoate-modifying Cu2+-detective Bodipy sensors with the fluorescent ON-OFF performance unaffected by molecular configuration
  作者：Yuting Chen、Luyang Zhao、Jianzhuang Jiang

  DOI：10.1016/j.saa.2016.12.034

  日期：2017.3

  revealed by the close torsion angle of C-C-O-C bridge, 174.15 and 171.81° for 1 and 2, respectively, despite the different dihedral angle between quinoline moiety and Bodipy fluorophore for 1 (73.46°) and 2 (82.26°) due to the steric hindrance originated from the C-1/C-7 methyl substituents on Bodipy core for the latter species. Systemic optical studies unravel the red-shifted absorption and fluorescence

  用8-羟基喹啉-萘甲酸酯部分修饰的两个新的硼二吡咯烷酮，即4,4-二氟-8-（5-（5-（8-羟基喹啉-萘甲酸酯））-3,5-二甲基-4-硼-3a，4a-二氮杂-s-茚并四烯（8-HQ-N-DMe-Bodipy）（1）和4,4-二氟-8-（5-（8-羟基喹啉-萘甲酸酯））-1,3,5,7-四甲基-4合成了-硼-3a，4a-二氮杂-s-茚并茂（8-HQ-N-TMe-Bodipy）（2）。单晶X射线衍射分析揭示了这两种化合物中8-羟基喹啉-萘甲酸酯部分的非常相似的空间排列，尽管CCOC桥的扭转角分别为174.15和171.81°（分别为1和2），但尽管存在不同，但仍显示出相似的空间排列由于空间位阻，喹啉部分与Bodipy荧光团之间的二面角分别为1（73.46°）和2（82.26°），这是由于后者的Bodipy核上的C-1 / C-7甲基取代基引起的。系统光学研究揭示了红移吸收和荧光发射，以及相
• Iodized BODIPY as a long wavelength light sensitizer for the near-infrared emission of ytterbium(iii) ion
  作者：Hongshan He、Liping Si、Yihan Zhong、Mukul Dubey

  DOI：10.1039/c2cc17037j

  日期：——

  Novel 8-HOQ–BODIPY–3I was developed as an efficient sensitizer for the near-infrared emission of ytterbium(III) ion at 980 nm under long wavelength excitation.

  新型 8-HOQ-BODIPY-3I 被开发为一种高效敏化剂，用于在长波长激发下在 980 nm 处发射近红外镱 (III) 离子。
• 8-Hydroxyquinoline-Substituted Boron–Dipyrromethene Compounds: Synthesis, Structure, and OFF–ON–OFF Type of pH-Sensing Properties
  作者：Yuting Chen、Hailong Wang、Liang Wan、Yongzhong Bian、Jianzhuang Jiang

  DOI：10.1021/jo200050a

  日期：2011.5.20

  A series of four novel 8-hydroxyquinoline-substituted boron-dipyrromethene derivatives, namely 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (1), 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5, 7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (2), 4,4-difluoro-8-(5-azastyryl-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a, 4a-diaza-s-indacene (3), and 4,4-difluoro-8-(5-azastyry1-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3 a,4a-diaza-s-indacene (4), have been synthesized and characterized by a series of spectroscopic methods. The molecular structures of 1 and 2 have been determined by single-crystal X-ray diffraction analyses. The two methyl substituents attached at C-1 and C-7 positions of boron-dipyrromethene (Bodipy) in compound 2 was revealed to prevent the free rotation of the 8-hydroxyquinoline (8-HQ) moiety, resulting in an almost vertical 8-HQ-Bodipy configuration of this compound. This is obviously different from those for 1 with the dihedral angle between 8-hydroxyquinoline and Bodipy moieties of 65.44 and 66.79 degrees due to the lack of methyl substituents in the latter compound. The intense fluorescence from the Bodipy subunit of these compounds was revealed to gradually get diminished along with either decreasing or increasing the pH value under acidic and basic conditions, respectively, in particular for 1, 2, and 4 because of the photoinduced intramolecular electron transfer from excited Bodipy moiety to 8-HQ unit and just an opposite process. This renders these compounds the first OFF-ON-OFF type of pH-dependent fluorescent sensors. Nevertheless, both the intrinsic fluorescence of these compounds and their fluorescent quenching properties along with the change in the pH value have been found to depend on the steric configuration as well as the linking group between 8-hydroxyquinoline and Bodipy moieties, revealing the effect of molecular structure on their fluorescence properties.