(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 | 1056477-91-8

• 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-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
• CAS: 1056477-91-8
• 化学式: C₁₄₀H₁₈₆BBr
• 分子量: 1959.73
• InChiKey: LLFGTSISWFDMCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  40.69
• 重原子数：
  142.0
• 可旋转键数：
  63.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  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 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以93%的产率得到2-dimesitylboron-6,6,15,15-tetra(p-octylphenyl)-9,9,18,18-tetraoctyl(ladder-type pentaphenylene)
  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
• 作为产物：
  描述：

  二(三甲苯基)氟化硼 、 10,27-Dibromo-7,7,24,24-tetraoctyl-17,17,34,34-tetrakis(4-octylphenyl)nonacyclo[18.14.0.03,18.04,16.06,14.08,13.021,33.023,31.025,30]tetratriaconta-1(20),2,4(16),5,8(13),9,11,14,18,21(33),22,25(30),26,28,31-pentadecaene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以36%的产率得到(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
  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