11-(dimesitylboraneyl)-9,9,18,18-tetraoctyl-6,6,15,15-tetrakis(4-octylphenyl)-N,N-di-p-tolyl-6,9,15,18-tetrahydro-s-indaceno[1,2-b:5,6-b']difluoren-2-amine | 1056477-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 11-(dimesitylboraneyl)-9,9,18,18-tetraoctyl-6,6,15,15-tetrakis(4-octylphenyl)-N,N-di-p-tolyl-6,9,15,18-tetrahydro-s-indaceno[1,2-b:5,6-b']difluoren-2-amine
• CAS: 1056477-93-0
• 化学式: C₁₅₄H₂₀₀BN
• 分子量: 2076.1
• InChiKey: FVDKOFJSQAFZRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  44.01
• 重原子数：
  156.0
• 可旋转键数：
  66.0
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (11-bromo-9,9,18,18-tetraoctyl-6,6,15,15-tetrakis(4-octylphenyl)-6,9,15,18-tetrahydro-s-indaceno[1,2-b:5,6-b']difluoren-2-yl)dimesitylborane 、 4,4'-二甲基二苯胺 在 三叔丁基膦 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 、 正己烷 为溶剂， 反应 8.0h， 以74%的产率得到11-(dimesitylboraneyl)-9,9,18,18-tetraoctyl-6,6,15,15-tetrakis(4-octylphenyl)-N,N-di-p-tolyl-6,9,15,18-tetrahydro-s-indaceno[1,2-b:5,6-b']difluoren-2-amine
  参考文献：
  名称：

  Mesitylboron-Substituted Ladder-Type Pentaphenylenes: Charge-Transfer, Electronic Communication, and Sensing Properties

  摘要：

  A series of dimesitylboron (B)- or ditolylamino (N)-substituted ladder-type pentaphenylenes (PP) has been designed and synthesized. The UV-vis absorption spectra of compounds BPPN, BPPB, and NPPN reveal an identical maximum wavelength at 432 rim, which indicates that the B and N centers have very similar contributions to the extended conjugation. A rather weak solvatochromism in the UV-vis absorption spectra is observed for compound BPPN, while a remarkable solvatochromic emission is achieved even though the distance between the B and the N centers is as huge as 22 angstrom. The photoluminescence of BPPN shows a bathochromic shift of 108 nm when the solvent polarity is increased from cyclohexane (453 nm) to acetone (561 nm). Compound BPPN acts as a colorimetric and fluorescent chemosensor with high sensitivity (10(-5) M) and selectivity for F- over other halogen ions. By inhibiting the charge transfer (CT) from the N center to the B center, the intense green CT emission of compound BPPN rapidly switches into the sky-blue emission of PP when F- is bound to the B center. Furthermore, a CT emission can be switched "on" and "off" when compound BPPB is used as F- sensory material. Such an intramolecular CT emission between the two B centers has so far never been reported. Corresponding studies by cyclic voltammetry and differential pulse voltammetry reveal a two-step reduction of the two bridged B centers in compound BPPB, which might suggest that the charge delocalizes through the whole molecule and that the terminal redox centers communicate through the pentaphenylene bridge.

  DOI：

  10.1021/ja803627x