4,9-bis((4-(diphenylamino)phenyl)ethynyl)-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 1426582-13-9

• 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: 4,9-bis((4-(diphenylamino)phenyl)ethynyl)-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• CAS: 1426582-13-9
• 化学式: C₉₄H₁₁₂N₄O₄
• 分子量: 1361.95
• InChiKey: CUHHSAOKJLKDGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.57
• 重原子数：
  102.0
• 可旋转键数：
  42.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.24
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,9-bis((4-(diphenylamino)phenyl)ethynyl)-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 、 双三氟甲烷磺酰亚胺 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Extended π-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials

  摘要：

  In this paper, a new synthetic way to modify naphthalene diimide (NDI) at "shoulder" positions is reported. The key step of the transformation is the intramolecular cyclization involving ethynyl and imidecarbonyl groups. The structure of the intermediate pyrylium cation was confirmed by X-ray crystal structural analysis. New conjugated molecules 1a-g were successfully synthesized in acceptable yields. Their absorption and fluorescence spectra were measured. Among them 1c-f are strongly emissive in solutions. Furthermore, 1b-f are also fluorescent in their solid states; in particular, 1b exhibits a typical aggregation-induced enhanced emission feature. Yellow-emissive microfibrils of Id show potential optical waveguide behavior. HOMO/LUMO energies of 1a-f were determined based on their cyclic voltammograms. The results also reveal that HOMO/LUMO energies of these new conjugated molecules are influenced by the two flanking moieties. Notably, the thin film of 1c that is emissive shows p-type semiconducting behavior with hole mobility up to 0.0063 cm(2) V-1 s(-1) based on the transfer and output characteristics of the OFET (organic field effect transistor).

  DOI：

  10.1021/jo302677k
• 作为产物：
  描述：

  4,9-二溴-2,7-二(2-辛基十二烷基)苯并[lmn][3,8]邻二氮杂菲-1,3,6,8(2H,7H)-四酮 、 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以84%的产率得到4,9-bis((4-(diphenylamino)phenyl)ethynyl)-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  参考文献：
  名称：

  Extended π-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials

  摘要：

  In this paper, a new synthetic way to modify naphthalene diimide (NDI) at "shoulder" positions is reported. The key step of the transformation is the intramolecular cyclization involving ethynyl and imidecarbonyl groups. The structure of the intermediate pyrylium cation was confirmed by X-ray crystal structural analysis. New conjugated molecules 1a-g were successfully synthesized in acceptable yields. Their absorption and fluorescence spectra were measured. Among them 1c-f are strongly emissive in solutions. Furthermore, 1b-f are also fluorescent in their solid states; in particular, 1b exhibits a typical aggregation-induced enhanced emission feature. Yellow-emissive microfibrils of Id show potential optical waveguide behavior. HOMO/LUMO energies of 1a-f were determined based on their cyclic voltammograms. The results also reveal that HOMO/LUMO energies of these new conjugated molecules are influenced by the two flanking moieties. Notably, the thin film of 1c that is emissive shows p-type semiconducting behavior with hole mobility up to 0.0063 cm(2) V-1 s(-1) based on the transfer and output characteristics of the OFET (organic field effect transistor).

  DOI：

  10.1021/jo302677k