phenyl-boron subphthalocyanine | 163616-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phenyl-boron subphthalocyanine
• 英文别名: phenyl-BsubPc；phenylsubphthalocyaninatoboron；Phenylsubphthalocyaninatobor；1-Phenyl-11,20,29,30,31-pentaza-2-azonia-1-boranuidanonacyclo[17.10.1.13,28.02,10.04,9.012,30.013,18.021,29.022,27]hentriaconta-2(10),3(31),4,6,8,11,13,15,17,19,21,23,25,27-tetradecaene
• CAS: 163616-02-2
• 化学式: C₃₀H₁₇BN₆
• 分子量: 472.316
• InChiKey: WCFIAWCKCAZYBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  1
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四苯硼钠 以 甲醇 为溶剂， 生成 phenyl-boron subphthalocyanine
  参考文献：
  名称：

  硼次酞菁的合成及结构表征

  摘要：

  卤代亚酞菁硼，[B (X) spc] (X = F, Cl, Br) 当邻苯二甲腈与三卤化硼在喹啉 (X = F) 或相应的卤代苯中加热时形成。[B (C6H5) spc] 由邻苯二甲腈和硼酸四苯酯或四苯氧化硼制备。[B (Br) spc]用于在吡啶/HOR中通过配体取代制备[B (OR) spc] (R = H, CH (CH3) 2, C (CH3) 3, C6H5)。[B (OOCR) spc] (R = H, CX3 (X = H, Cl, F), CH2X (X = Cl, C6H5), C6H5) 最终通过将 [B (Br) spc] 替换为相应的羧酸，用作溶剂。配合物的电化学特性以及 UV-VIS、IR/FIR、共​​振拉曼和 1H/10B-NMR 光谱。典型的 B – X 伸缩振动为 622 (X = Br)、950 (Cl)、1063 (F)、1096 cm – 1 (OH)

  DOI：

  10.1002/(sici)1521-3749(200002)626:2<588::aid-zaac588>3.0.co;2-b

文献信息

• Triflate-Subphthalocyanines: Versatile, Reactive Intermediates for Axial Functionalization at the Boron Atom
  作者：Julia Guilleme、David González-Rodríguez、Tomas Torres

  DOI：10.1002/anie.201007240

  日期：2011.4.4

  On the leave: Easily generated triflate boron subphthalocyanines are highly activated universal substrates for efficient axial substitution reactions with oxygen, sulfur, nitrogen, and carbon nucleophiles (see picture).

  休假：容易产生的三氟甲磺酸硼亚酞菁硼是高度活化的通用底物，可与氧，硫，氮和碳亲核试剂进行有效的轴向取代反应（见图）。
• Subphthalocyanines Having Axial Substituent with Direct B–C Bond: General Preparation and Physical Properties
  作者：Yasuhiro Yamasaki、Tomohiro Mori

  DOI：10.1246/cl.2010.1108

  日期：2010.10.5

  A novel synthetic methodology and the characterization of subphthalocyanines (SubPcs) having an axial substituent with a direct boron–carbon bond are reported. The SubPcs are found to be more light...

  报道了一种新的合成方法和对具有直接硼-碳键的轴向取代基的亚酞菁 (SubPcs) 的表征。发现 SubPcs 更轻...
• Aryl-Substituted Boron Subphthalocyanines and their Application in Organic Photovoltaics
  作者：Catherine Bonnier、David S. Josey、Timothy P. Bender

  DOI：10.1071/ch15381

  日期：——

  A family of five axial aryl-substituted boron subphthalocyanine (BsubPc) derivatives bearing a hydrido, methyl, methoxy, phenyl, or fluoro substituent at the para position of the aryl were synthesised from Br-BsubPc and the corresponding aryl Grignard reagent in moderate yields. The physicochemical characterisation of these derivatives gave similar absorption, photoluminescence, and cyclic voltammetry profiles and photoluminescence quantum yields, indicating that the nature of the substituent at the para position does not influence the basic photophysical properties of this generic class of BsubPcs. Conversely, the solid-state structural arrangement obtained from single crystals is highly dependent on the para substituent; for the non-polar hydrido, methyl, and phenyl substituents, only concave isoindole π interactions are present. Substitution for the polar methoxy or fluoro ligand affords one-dimensional ribbons formed by convex π interactions, where these ribbons further interact through concave isoindole π interactions with the adjacent ribbon, creating an extended two-dimensional π network. On incorporation of the hydrido, methyl, and fluoro derivatives into organic photovoltaic (OPV) devices, similar results and device metrics were obtained with the methyl and fluoro derivatives. Both, however, were significantly outperformed by the hydrido derivative. The uniqueness of the hydrido derivative is only realised once incorporated into OPVs as it shares the same basic physical properties as the other derivatives. Given these findings, we identify the hydrido derivative as the aryl-BsubPc with the most promise for future work in OPVs.

  我们以 Br-BsubPc 和相应的芳基格氏试剂为原料，以中等产率合成了五种轴向芳基取代的亚酞菁硼（BsubPc）衍生物，这些衍生物在芳基的对位上具有氢基、甲基、甲氧基、苯基或氟取代基。这些衍生物的物理化学特性具有相似的吸收、光致发光、循环伏安曲线和光致发光量子产率，表明对位取代基的性质并不影响这一类 BsubPc 的基本光物理特性。相反，从单晶体中获得的固态结构排列在很大程度上取决于对位取代基；对于非极性的水螅、甲基和苯基取代基，只存在凹异吲哚 π 相互作用。取代极性甲氧基或氟配体后，通过凸π相互作用形成一维带状结构，这些带状结构通过凹异吲哚π相互作用与相邻的带状结构进一步相互作用，形成一个扩展的二维π网络。在将氢rido、甲基和氟衍生物加入有机光伏（OPV）器件时，甲基和氟衍生物获得了相似的结果和器件指标。但是，甲基和氟衍生物的性能明显优于氢rido 衍生物。由于氢rido 衍生物与其他衍生物具有相同的基本物理性质，因此只有在加入 OPV 后才能体现出其独特性。鉴于这些发现，我们认为氢rido 衍生物是未来最有希望用于 OPV 的芳基-BsubPc。