2,6-diiodo-1,3,5,7-tetramethyl-8-(4-hydrox-3,5-diiodoyphenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1434003-46-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,6-diiodo-1,3,5,7-tetramethyl-8-(4-hydrox-3,5-diiodoyphenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-(4-hydroxy-3,5-diiodophenyl)-2,6-diiodo-1,3,5,7-tetramethyl-4-bora-3a, 4a-diaza-s-indacene；4,4-difluoro-2,6-diiodo-1,3,5,7-tetramethyl-8-(4′-hydroxy-3′,5′-diiodophenyl)-4-bora-3a,4a-diaza-s-indacene；4-(2,2-Difluoro-5,11-diiodo-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)-2,6-diiodophenol
• CAS: 1434003-46-9
• 化学式: C₁₉H₁₅BF₂I₄N₂O
• 分子量: 843.767
• InChiKey: OPUMUBWXOLBWIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-8-(4-hydroxyphenyl)-4-bora-3a,4a-diaza-s-indacene 在 碘 、 碘酸 作用下， 以 乙醇 为溶剂， 以61%的产率得到2,6-diiodo-1,3,5,7-tetramethyl-8-(4-hydrox-3,5-diiodoyphenyl)-4,4-difluoro-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

• 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。
• Effect of iodine substitution pattern on the singlet oxygen generation and solvent depended keto-enol tautomerization behavior of BODIPY photosensitizers
  作者：Baybars Köksoy、Esra Nur Kaya、Ferda Hacıvelioğlu、Serkan Yeşilot、Mahmut Durmuş

  DOI：10.1016/j.dyepig.2017.01.067

  日期：2017.5

  The novel iodinated-BODIPY derivatives (la and 1c) containing one or three iodine atoms were synthesized for the first time. The photochemical and photophysical properties of these BODIPYs were investigated and results were compared with two (lb) and four (1d) iodine bearing BODIPY derivatives. Surprisingly, the addition of iodine atoms to the meso-aryl positions of the phenyl moiety caused a color change due to the transformation of the enol form of the aromatic OH group to its keto form depending on the using solvent. This solvent affected keto-enol tautomerization on the BODIPY compounds was determined for the first time.