2,2-Difluoro-20-(2,4,6-trimethylphenyl)-3-aza-1-azonia-2-boranuidanonacyclo[19.15.0.03,19.04,17.05,10.011,16.023,36.024,29.030,35]hexatriaconta-1(36),4(17),5,7,9,11,13,15,18,20,22,24,26,28,30,32,34-heptadecaene | 1356355-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,2-Difluoro-20-(2,4,6-trimethylphenyl)-3-aza-1-azonia-2-boranuidanonacyclo[19.15.0.03,19.04,17.05,10.011,16.023,36.024,29.030,35]hexatriaconta-1(36),4(17),5,7,9,11,13,15,18,20,22,24,26,28,30,32,34-heptadecaene
• CAS: 1356355-17-3
• 化学式: C₄₂H₂₉BF₂N₂
• 分子量: 610.513
• InChiKey: SSRCHNLBIKIQPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  47
• 可旋转键数：
  1
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-Difluoro-5,11-bis(2-phenylphenyl)-8-(2,4,6-trimethylphenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene 在 三氟化硼乙醚 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以65%的产率得到2,2-Difluoro-20-(2,4,6-trimethylphenyl)-3-aza-1-azonia-2-boranuidanonacyclo[19.15.0.03,19.04,17.05,10.011,16.023,36.024,29.030,35]hexatriaconta-1(36),4(17),5,7,9,11,13,15,18,20,22,24,26,28,30,32,34-heptadecaene
  参考文献：
  名称：

  Facile Synthesis of Biphenyl-Fused BODIPY and Its Property

  摘要：

  A biphenyl-fused BODIPY was synthesized through a facile oxidative cyclization of peripheral aryl-substituents at the beta-position of the BODIPY unit. The extended pi-system of the fused BODIPY induces near-infrared (NIR) absorption and strong pi-pi interactions in the solid state. These features are beneficial for the application of the dye as a functional material. The biphenyl-fused BODIPY dye was demonstrated to exhibit photocurrent conversion ability on the basis of its n-type semiconducting property.

  DOI：

  10.1021/ol2033916

文献信息

• Phenanthro[<i>b</i>]-Fused BODIPYs through Tandem Suzuki and Oxidative Aromatic Couplings: Synthesis and Photophysical Properties
  作者：Wei Miao、Yuanmei Feng、Qinghua Wu、Wanle Sheng、Mao Li、Qingyun Liu、Erhong Hao、Lijuan Jiao

  DOI：10.1021/acs.joc.9b01425

  日期：2019.8.2

  A new synthetic method to build phenanthrene-fused boron dipyrromethenes (BODIPYs) through tandem Suzuki couplings on readily available 2,3,5,6-tetrabromoBODIPYs, followed by an intramolecular oxidative aromatic coupling mediated by iron(III) chloride is reported. This efficient synthesis allows a very straightforward approach for tuning the absorption and emission of BODIPYs in the red/near-infrared

  报道了一种新的合成方法，该方法通过在易于获得的2,3,5,6-tetrabromoBODIPYs上串联Suzuki偶合，然后通过由氯化铁（III）介导的分子内氧化性芳族偶合，来构建菲稠合的硼二茂铁（BODIPYs）。这种有效的合成方法提供了一种非常简单的方法来调节红色/近红外（NIR）范围内BODIPY的吸收和发射。这些生成的与菲融合的BODIPY具有很强的吸收性（消光系数高达2.2×10 5 M –1 cm –1），并且在近红外（NIR）范围内（688-754 nm）发射。所得菲环上的取代基对这些菲稠合的BODIPY的光物理性质有重大影响。