(9R,10S,11R,15S)-13-(tridecan-7-yl)-1,4-bis((triisopropylsilyl)ethynyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione | 913609-27-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (9R,10S,11R,15S)-13-(tridecan-7-yl)-1,4-bis((triisopropylsilyl)ethynyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione
• CAS: 913609-27-5
• 化学式: C₅₃H₇₉NO₂Si₂
• 分子量: 818.387
• InChiKey: BHOCEKQVXIFCDL-YSMXEILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.33
• 重原子数：
  58.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (9R,10S,11R,15S)-13-(tridecan-7-yl)-1,4-bis((triisopropylsilyl)ethynyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(9R,10S,11R,15S)-1,4-diethynyl-13-(tridecan-7-yl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione
  参考文献：
  名称：

  Conjugated Polymers in an Arene Sandwich

  摘要：

  A series of poly(p-arylene butadiynylene)s containing zero, one, and two co-facial pi-pi interactions per repeat unit were synthesized and characterized. A surprisingly selective and high-yielding Diels-Alder cycloaddition of anthracene and nonsymmetric, sterically hindered anhydrides proved essential to generating the cofacial arene-containing monomers. Single-crystal X-ray structures display nearly parallel cofacial arenes that are within the van der Waals contact distances. The precursor molecules with cofacial arenes undergo reversible one- and two-electron oxidations to the radical cation and dication in CH2Cl2. The anhydrides were converted to N-alkyl imides to increase the solubility. High-molecular weight poly(p-arylene butadiynylene)s were prepared via Pd/Cu(I)/benzoquinone oxidative coupling of the diacetylene monomers. The resulting polymers are highly emissive in solution and thin films. The ionization potentials were measured using ultraviolet photoelectron spectroscopy with thin films. Last, fluorescence measurements of polymer thin films during continuous irradiation indicate that the most hindered polymer is more resistant to photobleaching.

  DOI：

  10.1021/ja0648099
• 作为产物：
  描述：

  Tri(propan-2-yl)-[2-[4-[2-tri(propan-2-yl)silylethynyl]anthracen-1-yl]ethynyl]silane 在 咪唑 作用下， 以 甲苯 为溶剂， 生成 (9R,10S,11R,15S)-13-(tridecan-7-yl)-1,4-bis((triisopropylsilyl)ethynyl)-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione
  参考文献：
  名称：

  Conjugated Polymers in an Arene Sandwich

  摘要：

  A series of poly(p-arylene butadiynylene)s containing zero, one, and two co-facial pi-pi interactions per repeat unit were synthesized and characterized. A surprisingly selective and high-yielding Diels-Alder cycloaddition of anthracene and nonsymmetric, sterically hindered anhydrides proved essential to generating the cofacial arene-containing monomers. Single-crystal X-ray structures display nearly parallel cofacial arenes that are within the van der Waals contact distances. The precursor molecules with cofacial arenes undergo reversible one- and two-electron oxidations to the radical cation and dication in CH2Cl2. The anhydrides were converted to N-alkyl imides to increase the solubility. High-molecular weight poly(p-arylene butadiynylene)s were prepared via Pd/Cu(I)/benzoquinone oxidative coupling of the diacetylene monomers. The resulting polymers are highly emissive in solution and thin films. The ionization potentials were measured using ultraviolet photoelectron spectroscopy with thin films. Last, fluorescence measurements of polymer thin films during continuous irradiation indicate that the most hindered polymer is more resistant to photobleaching.

  DOI：

  10.1021/ja0648099