4,4-bis(4-methoxyphenyl)-1,3,5,7,8-pentamethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene | 908039-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4-bis(4-methoxyphenyl)-1,3,5,7,8-pentamethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 5,11-Diethyl-2,2-bis(4-methoxyphenyl)-4,6,8,10,12-pentamethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 908039-96-3
• 化学式: C₃₂H₃₉BN₂O₂
• 分子量: 494.485
• InChiKey: YWJLBKIENINOGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  26.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯甲醚 、 硼,[3-乙基-5-[1-(4-乙基-3,5-二甲基-2H-吡咯-2-亚基-kN)乙基]-2,4-二甲基-1H-吡咯酸根-kN]二氟-,(T-4)- 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以40%的产率得到4,4-bis(4-methoxyphenyl)-1,3,5,7,8-pentamethyl-2,4-diethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis and Photophysical Properties of Borondipyrromethene Dyes Bearing Aryl Substituents at the Boron Center

  摘要：

  Several borondipyrromethene (Bodipy) dyes bearing an aryl nucleus linked directly to the boron center have been prepared under mild conditions. The choice of Grignard or lithio organo-metallic reagents allows the isolation of B(F)(aryl) or B(aryl)(2) derivatives; where aryl refers to phenyl, anisyl, naphthyl, or pyrenyl fragments. A single crystal, X-ray structure determination for the bis-anisyl compound shows that the sp(3) hybridized boron center remains pseudo-tetrahedral and that the B-C bond distances are 1.615 and 1.636 angstrom. All compounds are electrode active but replacement of the fluorine atoms by aryl fragments renders the Bodipy unit more easily oxidized by 100 mV in the B(F)(aryl) and 180 mV in the B(aryl)(2) compounds whereas reduction is made more difficult by a comparable amount. Strong fluorescence is observed from the Bodipy fluorophore present in each of the new dyes, with the radiative rate constant being independent of the nature of the aryl substituent. The fluorescence quantum yields are solvent dependent and, at least in some cases (aryl = anisyl or pyrenyl), nonradiative decay from the first-excited singlet state is strongly activated. There is no indication, however, for population of a charge-transfer state, in which the aryl substituent acts as donor and the Bodipy fragment functions as acceptor, that is strongly coupled to the ground state. Instead, it is conjectured that nonradiative decay involves a conformational change driven by the solvophobic effect. Thus, the rate of nonradiative decay in any given solvent increases with increasing surface accessibility (or molar volume) of the aryl substituent. Intramolecular energy transfer from pyrene or naphthalene residues to Bodipy is quantitative.

  DOI：

  10.1021/ja062405a