4,4-difluoro-3,7-bis(p-methoxystyryl)-1,7-dimethyl-8-(p-iodophenyl)-4-bora-3a,4a-diaza-s-indacene | 1189528-66-2

• 英文名称: 4,4-difluoro-3,7-bis(p-methoxystyryl)-1,7-dimethyl-8-(p-iodophenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(4-iodophenyl)-1,7-dimethyl-3,5-bis(4-methoxystyryl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；4,4-difluoro-3,5-di(4-methoxystyryl)-1,7-dimethyl-8-(p-iodophenyl)-4-bora-3a,4a-diaza-s-indacene；4,4-difluoro-3,7-di-p-methoxystyryl-1,7-dimethyl-8-p-iodophenyl-4-bora-3a,4a-diaza-s-indacene
• CAS: 1189528-66-2；1260903-50-1
• 化学式: C₃₅H₃₀BF₂IN₂O₂
• 分子量: 686.348
• InChiKey: IVRDQOFUKYHVFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  4,4-difluoro-3,7-bis(p-methoxystyryl)-1,7-dimethyl-8-(p-iodophenyl)-4-bora-3a,4a-diaza-s-indacene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.25h， 生成
  参考文献：
  名称：

  用于红光下细胞成像和线粒体靶向光动力治疗的铂 (II) 硼-二吡咯亚甲基络合物

  摘要：

  Acacplatin-RB是一种顺铂类似物，具有附加有乙酰丙酮的硼二吡咯亚甲基 (BODIPY) 染料，具有线粒体定位和显着的细胞凋亡红光诱导光动力疗法 (PDT)，形成单线态氧作为活性氧。此外，该复合物表现出线粒体膜电位的降低、光诱导条件下微管的破坏以及伤口愈合测定的抗转移特性。

  DOI：

  10.1002/asia.202300667
• 作为产物：
  描述：

  4-碘苯甲酰氯 在 哌啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 76.0h， 生成 4,4-difluoro-3,7-bis(p-methoxystyryl)-1,7-dimethyl-8-(p-iodophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Red and Blue Liquid-Crystalline Borondipyrromethene Dendrimers

  摘要：

  We have designed a series of modular arid fluorescent poly(arylester) dendrimers fimetionalized with cyanobiphenyl subunits and fluorescent borondipyrromethene (Bodipy) dyes. The green emitter is a Bodipy With four Methyl groups, and the Bodipy dye possessing extended conjugation with two methyl and two vinyl, groups acts as a red emitter. The design elerrient of these architectures relates to a secondary amide linkers interposed between the conventional Bodipy and the dendrons. The second- and thirdgeneration dendrimers give rise to ternatic and/or srneetic A phases, whereas the first generation clendrimers show smeCtie A and C phases or an unidentified meSophase. The novel materials are highly fluorescent in solution and in the as obtained powders but not in the ineSophaSe. Dilution of the dendritic dyes with the nonfluorekent acid dendron in the solid phase shifted the fluorescence to higher energy, and demonstrated the presence of aggregates in the solid state, Mixing the red and blue Materials in a solid, phase led to the observation of effective electronic energy transfer from the red dye to the blue one. Increasing the proportion of the red dye (energy donor) from 1 to 2,50 molar with respect to the blue dye (euergy acceptor) resulted in the observation of residual emission of the red dye in the solid state mixture. Increasing the proportion from 1 to 1000 resulted in equal emission in the 540 to 760 nm range.

  DOI：

  10.1021/cm503577y

文献信息

• New insights into the solubilization of Bodipy dyes
  作者：Song-Lin Niu、Gilles Ulrich、Pascal Retailleau、Jack Harrowfield、Raymond Ziessel

  DOI：10.1016/j.tetlet.2009.04.017

  日期：2009.7

  protection of sulfonate groups by pyrrole of indopyrrole appears efficient but the deprotection step does not offer viable routes. Conversion of the bromopyrene or iodo Bodipy compounds to sulfobetaine derivatives is feasible either by cross-coupling directly the ethynylsulfobetaine or by first cross-coupling 1-(N,N-dimethylamino)-prop-2-yne followed by quaternization of the dimethylamino residue with 1,3-propanesultone

  合成了具有各种取代基的几种Bodipy染料，这些取代基旨在改善水溶性。在不同的合成策略中，通过吲哚吡咯的吡咯保护磺酸盐基团似乎是有效的，但是脱保护步骤没有提供可行的途径。通过将乙炔基磺基甜菜碱直接交叉偶联或先将1-（N，N-二甲基氨基）-丙-2-炔进行交叉偶联，然后再将二甲基氨基残基季铵化，将溴化re或碘化的Bodipy化合物转化为磺基甜菜碱衍生物是可行的。 1,3-丙磺酸内酯。这些染料中的一些（Bodipy's和pyr）在水中可适当溶解，并且在极性溶剂和水中仍保持高荧光性。
• Dual Bodipy fluorophores linked by polyethyleneglycol spacers
  作者：Soumyaditya Mula、Gilles Ulrich、Raymond Ziessel

  DOI：10.1016/j.tetlet.2009.08.091

  日期：2009.11

  for the substitution of the fluoro groups on the boron by Grignard reagents. Single alkylation on the amino-Bodipy compounds by a polyethyleneglycol chain bearing an alkyne end group is feasible using a biphasic strategy. Linkage of a blue dye on the alkyne fragment is promoted by palladium(0) and it provides novel dual donor–acceptor dyes. Fluorescence of the monoalkylated amino dyes is heavily quenched

  合成了具有各种取代基的几种Bodipy染料，这些取代基旨在与包括质子在内的冒险阳离子发生相互作用。在不同的合成策略中，用BOC保护氨基对于用格氏试剂代替硼上的氟基似乎很有效。使用双相策略，通过带有炔基端基的聚乙二醇链对氨基-二联吡啶化合物进行单烷基化是可行的。钯（0）促进了炔烃片段上蓝色染料的键合，并提供了新颖的双供体-受体染料。单烷基化氨基染料的荧光被严重淬灭，但通过质子化或与Fe（II）盐相互作用而得以恢复。来自供体的非常有效的能量转移（能量输入为20,000 cm -1到受体的能量（在15,100 cm -1处的能量输出）是定量的，与距离无关。
• Energy Transfer by Way of an Exciplex Intermediate in Flexible Boron Dipyrromethene-Based Allosteric Architectures
  作者：Soumyaditya Mula、Kristopher Elliott、Anthony Harriman、Raymond Ziessel

  DOI：10.1021/jp106626v

  日期：2010.10.7

  connects the terminal dyes. A critical design element of this type of dyad relates to a secondary amine linkage interposed between the conventional Bodipy and the tether. Cyclic voltammetry shows both Bodipy dyes to be electroactive and indicates that the secondary amine is quite easily oxidized. The ensuing fluorescence quenching is best explained in terms of the rapid formation of an intermediate

  我们已经设计并合成了一系列模块化双色染料，其中包括作为黄色发射体的常规硼二吡咯亚甲基（Bodipy）染料，以及具有扩展共轭功能的Bodipy染料，其作为红色发射体。由乙二醇残基构成的可变长度的柔性束线连接末端染料。这种类型的二元组的关键设计元素涉及介于常规Bodipy和系链之间的仲胺键。循环伏安法表明两种Bodipy染料均具有电活性，并表明仲胺非常容易被氧化。最好用快速形成中间电荷转移状态来解释随后的荧光猝灭。实际上，在弱极性溶剂和临界温度范围内观察到激基复合物型发射。-1。用较高能量的吸收剂（即pyr）代替红色发射器，有助于收集近紫外光，并将虚拟斯托克斯位移扩展到8000 cm -1。分子内能量转移功效的调节是通过在某些阳离子存在下对连接器进行预组织来实现的。后者的行为是完全可逆的，对应于人为的变构效应。
• Improved push-pull-push E-Bodipy fluorophores for two-photon cell-imaging
  作者：Pascal Didier、Gilles Ulrich、Yves Mély、Raymond Ziessel

  DOI：10.1039/b911587k

  日期：——

  Quadrupolar Bodipy dyes exhibiting TPA activity and high brightness with an emission at 660 nm were synthesized and internalized in HeLa cells, whereupon FLIM experiments were conducted.

  合成了具有 TPA 活性和高亮度的四极 Bodipy 染料，其发射波长为 660 纳米，并将其内化到 HeLa 细胞中，然后进行了 FLIM 实验。
• Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation
  作者：Nerea Epelde-Elezcano、Eduardo Palao、Hegoi Manzano、Alejandro Prieto-Castañeda、Antonia R. Agarrabeitia、Andrea Tabero、Angeles Villanueva、Santiago de la Moya、Íñigo López-Arbeloa、Virginia Martínez-Martínez、María J. Ortiz

  DOI：10.1002/chem.201605822

  日期：2017.4.6

  library of halogen‐free photosensitizers (PS) based on orthogonal boron dipyrromethene (BODIPY) dimers are reported. Herein we establish key structural factors in order to enhance singlet oxygen generation by judiciously choosing the substitution patterns according to key electronic effects and synthetic accessibility factors. The photosensitization mechanism of orthogonal BODIPY dimers is demonstrated

  报道了基于正交硼二吡咯亚甲基（BODIPY）二聚体的无卤光敏剂（PS）新文库的合成，光物理特性和建模。在这里，我们建立关键的结构因素，以便通过根据关键的电子效应和合成可及性因素明智地选择取代模式来增强单线态氧的产生。正交BODIPY二聚体的光敏化机制通过自旋轨道电荷转移系统间穿越（SOCT-ISC）机制与它们的固有分子内电荷转移（ICT）特性密切相关。因此，可以通过溶剂极性以及其中一个BODIPY单元中存在给电子或吸电子基团来有效地调节单线态氧的产生。-6  m）。