4,4-difluoro-8-(4-methoxy-1-naphthyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4-difluoro-8-(4-methoxy-1-naphthyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 1,3,5,7-tetramethyl-8-(4-methoxynaphthalene-1-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；4,4-difluoro-8-meoxynaphthyl-1,3,5,7-tetramethyl-4-boron-3a,4a-diaza-s-indacene；5,5-Difluoro-10-(4-methoxy-1-naphthyl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；2,2-difluoro-8-(4-methoxynaphthalen-1-yl)-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 化学式: C₂₄H₂₃BF₂N₂O
• 分子量: 404.267
• InChiKey: BDGRLWVZXLUCMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-(4-methoxy-1-naphthyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 碘 、 碘酸 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 2,6-diiodo-1,3,5,7-tetramethyl-8-(4-methoxynaphthalene-1-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  一系列BODIPY的合成，光动力活性和定量构效关系模型

  摘要：

  这里，我们报告的11个新BODIPYs（合成14 - 24），其特征在于通过在8（芳香环的存在内消旋）的位置和碘原子对吡咯2,6位。这些分子中，连同已被我们（报道12个BODIPYs 1  -  12），代表BODIPYs表示不同的原子或基团作为芳族结构部分的取代基的一个大的面板。已经研究了两个物理化学特征（1 O 2生成速率和亲脂性），它们在光敏剂的结果中起着至关重要的作用。在体外在SKOV3细胞系中，在黑暗中处理细胞24小时，然后用绿色LED装置（通量25.2 J / cm 2）照射2 h，研究了23种PS的光诱导杀伤功效。用MTT试验评估细胞杀伤功效，并将其与内消旋未取代化合物之一进行比较（13）。为了理解取代基的可能作用，建立了基于理论整体分子描述符的预测定量构效关系（QSAR）回归模型。结果清楚地表明，芳环的存在是优异的光动力学响应的基础，而芳环上的电子效应和取代基的位置不影响光动力学功效。

  DOI：

  10.1016/j.jphotobiol.2017.01.012
• 作为产物：
  描述：

  4-甲氧基-1-萘甲醛 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4,4-difluoro-8-(4-methoxy-1-naphthyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis and photo-physical properties of a series of BODIPY dyes

  摘要：

  A series of 39 boron-dipyrrolylmethenes (BODIPYs) have been synthesized and characterized. Their spectroscopic properties, degree of lipophilicity, chemical stability under irradiation, and singlet-oxygen generation rate have also been studied. These compounds differ in the presence of ethyl groups (group A), hydrogens (group B) or iodines (group C) on the 2,6 positions; these appendices confer particular characteristics to each group. The presence of an aromatic substituent or hydrogen on the indacene 8 position produces 13 different molecules of each group. Besides the effects exerted by the group or atom on the 2,6 positions, the substituent on the 8 position exerts a further effect on the physico-chemical parameters, thus the desired properties of BODIPYs, concerning fluorescence, lipophilicity, and singlet oxygen production can be modulated accordingly. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.064

文献信息

• Attaching naphthalene derivatives onto BODIPY for generating excited triplet state and singlet oxygen: Tuning PET-based photosensitizer by electron donors
  作者：Xian-Fu Zhang、Nan Feng

  DOI：10.1016/j.saa.2017.08.005

  日期：2018.1

  a facile one pot reaction. The naphthalene functionalization of BODIPY leads up to a 5-fold increase in the formation efficiency of excited triplet state and singlet oxygen in polar solvents. Steady state and time resolved fluorescence, laser flash photolysis, and quantum chemistry methods were used to reveal the mechanism. All measured data and quantum chemical results suggest that these systems can

  内消旋-萘取代的以容易的一锅反应制备BODIPY化合物。BODIPY的萘功能化导致极性溶剂中激发三重态和单重态氧的形成效率提高5倍。稳态和时间分辨荧光，激光闪光光解和量子化学方法被用来揭示机理。所有测得的数据和量子化学结果表明，这些系统可以看作是电子给体-受体（DA）对（BODIPY充当受体），光诱导的电荷转移（PCT）或光诱导的电子转移（PET）在光激发（DA）时发生+hν→d δ+ -A δ -，0 <δ≤1）和诱导的三重态的形成（电荷复合d δ+-A δ -  →DA（T 1）。这些新颖的基于PCT或PET的光敏剂（PS）显示出与传统PS不同的功能，例如通过轻松的结构修饰实现的强大可调性以及对中等极性的良好选择性。这种PS的新特性可以导致在有机氧合反应和肿瘤的光动力疗法中的重要应用。
• Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching
  作者：Hisato Sunahara、Yasuteru Urano、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja068551y

  日期：2007.5.1

  We systematically examined the mechanism of the solvent polarity dependence of the fluorescence ON/OFF threshold of the BODIPY (boron dipyrromethene) fluorophore and the role of photoinduced electron transfer (PeT). In a series of BODIPY derivatives with variously substituted benzene moieties at the 8-position, the oxidation potential of the benzene moiety became more positive and the reduction potential of the BODIPY fluorophore became more negative as the solvent polarity was decreased; consequently, the free energy change of PeT from the benzene moiety becomes larger in a more nonpolar environment. Utilizing this finding, we designed and synthesized a library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity. These environment-sensitive probes were used to examine bovine serum albumin (BSA) and living cells. The polarity at the surface of albumin was concluded to be similar to that of acetone, while the polarity of the internal membranes of HeLa cells was similar to that of dichloromethane.
• Synthesis, photodynamic activity, and quantitative structure-activity relationship modelling of a series of BODIPYs
  作者：Enrico Caruso、Marzia Gariboldi、Alessandro Sangion、Paola Gramatica、Stefano Banfi

  DOI：10.1016/j.jphotobiol.2017.01.012

  日期：2017.2

  Here we report the synthesis of eleven new BODIPYs (14–24) characterized by the presence of an aromatic ring on the 8 (meso) position and of iodine atoms on the pyrrolic 2,6 positions. These molecules, together with twelve BODIPYs already reported by us (1 − 12), represent a large panel of BODIPYs showing different atoms or groups as substituent of the aromatic moiety. Two physico-chemical features

  这里，我们报告的11个新BODIPYs（合成14 - 24），其特征在于通过在8（芳香环的存在内消旋）的位置和碘原子对吡咯2,6位。这些分子中，连同已被我们（报道12个BODIPYs 1  -  12），代表BODIPYs表示不同的原子或基团作为芳族结构部分的取代基的一个大的面板。已经研究了两个物理化学特征（1 O 2生成速率和亲脂性），它们在光敏剂的结果中起着至关重要的作用。在体外在SKOV3细胞系中，在黑暗中处理细胞24小时，然后用绿色LED装置（通量25.2 J / cm 2）照射2 h，研究了23种PS的光诱导杀伤功效。用MTT试验评估细胞杀伤功效，并将其与内消旋未取代化合物之一进行比较（13）。为了理解取代基的可能作用，建立了基于理论整体分子描述符的预测定量构效关系（QSAR）回归模型。结果清楚地表明，芳环的存在是优异的光动力学响应的基础，而芳环上的电子效应和取代基的位置不影响光动力学功效。
• Synthesis and photo-physical properties of a series of BODIPY dyes
  作者：Stefano Banfi、Gianluca Nasini、Stefano Zaza、Enrico Caruso

  DOI：10.1016/j.tet.2013.04.064

  日期：2013.6

  A series of 39 boron-dipyrrolylmethenes (BODIPYs) have been synthesized and characterized. Their spectroscopic properties, degree of lipophilicity, chemical stability under irradiation, and singlet-oxygen generation rate have also been studied. These compounds differ in the presence of ethyl groups (group A), hydrogens (group B) or iodines (group C) on the 2,6 positions; these appendices confer particular characteristics to each group. The presence of an aromatic substituent or hydrogen on the indacene 8 position produces 13 different molecules of each group. Besides the effects exerted by the group or atom on the 2,6 positions, the substituent on the 8 position exerts a further effect on the physico-chemical parameters, thus the desired properties of BODIPYs, concerning fluorescence, lipophilicity, and singlet oxygen production can be modulated accordingly. (C) 2013 Elsevier Ltd. All rights reserved.