5,5'-(m-phenylene)bis[10-(4-n-butylphenyl)-5,10-dihydrophenazine] | 870538-39-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,5'-(m-phenylene)bis[10-(4-n-butylphenyl)-5,10-dihydrophenazine]
• 英文别名: 5,5'-(m-phenylene)bis(10-p-n-butylphenyl-5,10-dihydrophenazine)；5-(4-Butylphenyl)-10-[3-[10-(4-butylphenyl)phenazin-5-yl]phenyl]phenazine
• CAS: 870538-39-9
• 化学式: C₅₀H₄₆N₄
• 分子量: 702.942
• InChiKey: JRRMTNBUQYPRCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C(Solv: methanol (67-56-1); benzene (71-43-2))
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-(m-phenylene)bis[10-(4-n-butylphenyl)-5,10-dihydrophenazine] 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 乙腈 为溶剂， 以73%的产率得到
  参考文献：
  名称：

  Exchange Interaction of 5,5‘-(m- and p-Phenylene)bis(10-phenyl-5,10-dihydrophenazine) Dications and Related Analogues

  摘要：

  5,5'-(m-Phenylene)bis[(10-aryl-5,10-dihydroplienazine) dications, 3a(2+) and 3b(2+) and their p-analogues 4a(2+) and 4b(2+), were prepared, and their exchange interaction was investigated. The EPR spectra of these dications at 123 K in a butyronitrile matrix showed the population of a triplet state. The temperature dependence of the EPR signal intensity (vertical bar Delta m(s)vertical bar = 2) showed that these dications had singlet ground states with Delta E-ST/k(B) = -27 to -21 K for the m-isomer 3(2+) and with Delta E-ST/k(B) = -10 to -8 K for the p-isomer 4(2+). Theoretical calculation of the exchange interaction J for these dications at the orthogonal torsion angle geometries was carried out for 3a(2+) and 4a(2+) and for (m- and p-phenylene)bisphenothiazine dications 1(2+) and 221 using the broken-symmetry approach for the singlet states. A good correlation was observed between the calculated J and a MO-energy term in the triplet state, Delta E-TMO = vertical bar HOMO(alpha) - (HOMO - 1)(alpha)vertical bar. The calculated J values were negative in the order of 10 K for the m-dications (J/k(B) = -14.7 K for 12+, -11.5 K for 3a(2+)), but much smaller negative values were found for the p-isomers (J/k(B) = -0.9 K for 2(2+), -0.8 K for 4a2+). The smaller 1J1 values for the p-dications are qualitatively consistent with the experimental Delta E-ST (2J) values.

  DOI：

  10.1021/jo051791w
• 作为产物：
  描述：

  lithium,butylbenzene 在 三叔丁基膦 、 sodium t-butanolate 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 5,5'-(m-phenylene)bis[10-(4-n-butylphenyl)-5,10-dihydrophenazine]
  参考文献：
  名称：

  Facile Synthesis of 5,10-Diaryl-5,10-dihydrophenazines and Application to EL Devices

  摘要：

  An efficient method for the synthesis of 5,10-diaryldihydrophenazine was developed using a recently developed Pd(0)-mediated cross-coupling reaction. The products 1k and 3c showed excellent properties as hole injection materials in electroluminescent (EL) devices.

  DOI：

  10.1021/ol0274458

文献信息

• Facile Synthesis of 5,10-Diaryl-5,10-dihydrophenazines and Application to EL Devices
  作者：Toshihiro Okamoto、Eriko Terada、Masatoshi Kozaki、Manabu Uchida、Shingo Kikukawa、Keiji Okada

  DOI：10.1021/ol0274458

  日期：2003.2.1

  An efficient method for the synthesis of 5,10-diaryldihydrophenazine was developed using a recently developed Pd(0)-mediated cross-coupling reaction. The products 1k and 3c showed excellent properties as hole injection materials in electroluminescent (EL) devices.
• Exchange Interaction of 5,5‘-(<i>m</i>- and <i>p</i>-Phenylene)bis(10-phenyl-5,10-dihydrophenazine) Dications and Related Analogues
  作者：Eriko Terada、Toshihiro Okamoto、Masatoshi Kozaki、Miyuki Eiraku Masaki、Daisuke Shiomi、Kazunobu Sato、Takeji Takui、Keiji Okada

  DOI：10.1021/jo051791w

  日期：2005.11.1

  5,5'-(m-Phenylene)bis[(10-aryl-5,10-dihydroplienazine) dications, 3a(2+) and 3b(2+) and their p-analogues 4a(2+) and 4b(2+), were prepared, and their exchange interaction was investigated. The EPR spectra of these dications at 123 K in a butyronitrile matrix showed the population of a triplet state. The temperature dependence of the EPR signal intensity (vertical bar Delta m(s)vertical bar = 2) showed that these dications had singlet ground states with Delta E-ST/k(B) = -27 to -21 K for the m-isomer 3(2+) and with Delta E-ST/k(B) = -10 to -8 K for the p-isomer 4(2+). Theoretical calculation of the exchange interaction J for these dications at the orthogonal torsion angle geometries was carried out for 3a(2+) and 4a(2+) and for (m- and p-phenylene)bisphenothiazine dications 1(2+) and 221 using the broken-symmetry approach for the singlet states. A good correlation was observed between the calculated J and a MO-energy term in the triplet state, Delta E-TMO = vertical bar HOMO(alpha) - (HOMO - 1)(alpha)vertical bar. The calculated J values were negative in the order of 10 K for the m-dications (J/k(B) = -14.7 K for 12+, -11.5 K for 3a(2+)), but much smaller negative values were found for the p-isomers (J/k(B) = -0.9 K for 2(2+), -0.8 K for 4a2+). The smaller 1J1 values for the p-dications are qualitatively consistent with the experimental Delta E-ST (2J) values.