5,5'-(m-phenylene)bis(10-phenyl-5,10-dihydrophenazine) | 870527-85-8

• 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-phenyl-5,10-dihydrophenazine)
• 英文别名: 5-Phenyl-10-[3-(10-phenylphenazin-5-yl)phenyl]phenazine
• CAS: 870527-85-8
• 化学式: C₄₂H₃₀N₄
• 分子量: 590.727
• InChiKey: YGFWLGBKLKMODC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 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-phenyl-5,10-dihydrophenazine) 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 乙腈 为溶剂， 以76%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：

  酚嗪 在 palladium diacetate 、 三叔丁基膦 、 sodium t-butanolate 作用下， 以 乙醚 、 邻二甲苯 、 环己烷 为溶剂， 反应 4.5h， 生成 5,5'-(m-phenylene)bis(10-phenyl-5,10-dihydrophenazine)
  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

文献信息

• Multi-electron redox phenazine for ready-to-charge organic batteries
  作者：Minah Lee、Jihyun Hong、Byungju Lee、Kyojin Ku、Sechan Lee、Chan Beum Park、Kisuk Kang

  DOI：10.1039/c7gc00849j

  日期：——

  Organic redox compounds represent an emerging class of cathode materials in rechargeable batteries for low-cost and sustainable energy storage. However, the low operating voltage (< 3 V) and necessity of using lithium-containing anodes have significantly limited their practical applicability to battery systems. Here, we introduce a new class of p-type organic redox centers based on N, N’-substituted

  有机氧化还原化合物代表了可充电电池中用于低成本和可持续能源存储的新兴正极材料类别。但是，低工作电压（<3 V）和使用含锂阳极的必要性已大大限制了它们在电池系统中的实际适用性。在这里，我们介绍一种基于N，N'-取代的吩嗪（NSPZ）的新型p型有机氧化还原中心，以构建可充电的有机电池。在不存在含锂阳极的情况下，NSPZ阴极在3.7和3.1 V时伴随阴离子缔合促进了可逆的两电子转移，这在双离子电池中产生了622 Wh / kg的比能。
• ORGANISCHE MOLEKÜLE, INSBESONDERE ZUR VERWENDUNG IN OPTOELEKTRONISCHEN BAUELEMENTEN
  申请人：cynora GmbH

  公开号：EP3048155A1

  公开（公告）日：2016-07-27

  Die Erfindung betrifft organische Moleküle, insbesondere zur Verwendung in optoelektronischen Bauelementen, wie OLED. Erfindungsgemäß weist das organische Molekül eine Struktur der Formel 1 auf wobei in Formel 1 gilt: w sind unabhängig voneinander ausgewählt aus sp2-hybridisiertem Kohlenstoff, sp3-hybridisiertem Kohlenstoff, sp2-hybridisiertem Silizium, sp3-hybridisiertem Silizium, sp2-hybridisiertem Stickstoff, sp3-hybridisiertem Stickstoff, oder eine direkte Bindung, wobei in einem erfindungsgemäßen Molekül jeweils nur ein w eine direkte Bindung sein kann und wobei das zyklische Gerüst aus w, x, y maximal 3 Atome aufweist, die nicht gleich Kohlenstoff sind; x ist ausgewählt aus sp2-hybridisierten Kohlenstoff, sp2-hybridisierten Silizium oder sp2-hybridisierten Stickstoff; y ist ausgewählt aus sp2-hybridisierten Kohlenstoff, sp2-hybridisierten Silizium oder sp2-hybridisierten Stickstoff; n kann alle ganzzahligen Werte von 2 bis q annehmen, wobei q der Gesamtzahl der substituierbaren H-Atome des zyklischen Gerüsts aus w, x, y entspricht; R** ist entweder ein Rest R* oder eine chemische Einheit AF, wobei in Formel 1 mindestens zwei R** gleich AF sein müssen, wobei mindestens zwei unterschiedliche chemische Einheiten AF1 und AF2 enthalten sind, wobei die Einheiten AF ausgewählt sind aus den in Tabelle 3 aufgeführten Strukturen.

  本发明涉及有机分子，特别是用于光电设备（如有机发光二极管）的有机分子。根据本发明，有机分子具有式 1 的结构 式 1 中 w独立地选自sp2-杂化碳、sp3-杂化碳、sp2-杂化硅、sp3-杂化硅、sp2-杂化氮、sp3-杂化氮或直接键，其中在根据本发明的分子中，每次只能有一个w是直接键，并且 其中 w、x、y 的环状骨架最多有 3 个不等同于碳的原子； x 选自 sp2-杂化碳、sp2-杂化硅或 sp2-杂化氮； y 选自 sp2-杂化碳、sp2-杂化硅或 sp2-杂化氮； n 可以是 2 到 q 之间的所有整数值，其中 q 相当于 w、x、y 的环状结构中可被取代的 H 原子的总数； R** 是自由基 R* 或化学单元 AF，其中在式 1 中，至少两个 R** 必须等于 AF，其中至少包含两个不同的化学单元 AF1 和 AF2，其中单元 AF 选自表 3 所列结构。
• 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.