2,7-dioctyl-9,10-phenanthrenequinone | 1603928-57-9

• 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: 2,7-dioctyl-9,10-phenanthrenequinone
• 英文别名: 2,7-Dioctylphenanthrene-9,10-dione
• CAS: 1603928-57-9
• 化学式: C₃₀H₄₀O₂
• 分子量: 432.646
• InChiKey: ONHTWADVNLUGKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,7-dioctyl-9,10-phenanthrenequinone 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 10,13-bis(5-bromo-4-hexylthiophen-2-yl)-2,7-dioctyldibenzo[a,c]phenazine
  参考文献：
  名称：

  2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体及其 制备方法与聚合物

  摘要：

  本发明涉及2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体及其制备方法与聚合物。所述的2,7-烷基取代菲并[9,10-b]吡嗪衍生物单元具有大π共轭刚性平面和较强的电子亲和势。2,7-烷基的引入在提高该类单体或相关聚合物的分子量、溶解性、可加工或自组装等方面的性能起着关键性的作用。2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体的合成通过菲醌的溴化、还原、羟基保护、2,7-烷基化、发烟硝酸氧化脱保护和关环等步骤，合成纯化容易，原料价格低廉，有利于大量生产。2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体通过Suzuki、Stille或Yamamoto聚合反应可获得均聚物或共聚物。该系列聚合物在有机溶剂中具有良好的溶解性，适合于溶液加工，在有机平板显示、光伏电池以及有机场效应晶体管领域中有着广泛的应用前景。

  公开号：

  CN103724283B
• 作为产物：
  描述：

  2,7-dibromo-9,10-diethoxylphenanthrene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 硝酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 2,7-dioctyl-9,10-phenanthrenequinone
  参考文献：
  名称：

  2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体及其 制备方法与聚合物

  摘要：

  本发明涉及2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体及其制备方法与聚合物。所述的2,7-烷基取代菲并[9,10-b]吡嗪衍生物单元具有大π共轭刚性平面和较强的电子亲和势。2,7-烷基的引入在提高该类单体或相关聚合物的分子量、溶解性、可加工或自组装等方面的性能起着关键性的作用。2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体的合成通过菲醌的溴化、还原、羟基保护、2,7-烷基化、发烟硝酸氧化脱保护和关环等步骤，合成纯化容易，原料价格低廉，有利于大量生产。2,7-烷基取代菲并[9,10-b]吡嗪衍生物单体通过Suzuki、Stille或Yamamoto聚合反应可获得均聚物或共聚物。该系列聚合物在有机溶剂中具有良好的溶解性，适合于溶液加工，在有机平板显示、光伏电池以及有机场效应晶体管领域中有着广泛的应用前景。

  公开号：

  CN103724283B

文献信息

• σ–π and p–π conjugation induced NIR-emitting iridium(<scp>iii</scp>) complexes anchored by flexible side chains in a rigid dibenzo[<i>a</i>,<i>c</i>]phenazine moiety and their application in highly efficient solution-processable NIR-emitting devices
  作者：Caifa You、Denghui Liu、Mengbing Zhu、Junting Yu、Bin Zhang、Yu Liu、Yafei Wang、Weiguo Zhu

  DOI：10.1039/d0tc00479k

  日期：——

  photoluminescence (PL) and electroluminescence (EL) properties, and to obtain high-efficiency near-infrared (NIR)-emitting iridium(III) complexes, in this work, two rigid C^N ligands of dibenzo[a,c]phenazine (DBPz) derivatives, respectively, anchored by flexible side chains of n-octyl and n-octyloxy and their corresponding iridium(III) complexes of Ir-R and Ir-OR were designed and synthesized. Their photophysical

  为了系统地研究σ–π和p–π共轭对光致发光（PL）和电致发光（EL）性质的影响，并获得高效的近红外（NIR）发射铱（III）配合物，在这项工作中，两个二苯并[刚性C ^ N配体一，ç ]吩嗪（DBPz）衍生物，分别由的柔性侧链锚定ñ辛基和ñ -octyloxy及其相应的铱（III）配合物的Ir-R和铱OR是设计和合成。系统地研究了它们的光物理和电致发光特性。结果发现，σ-π和p-π共轭效应可以使铱（III与没有任何侧链的原型铱配合物相比，该配合物表现出明显的红移NIR发射，具有高的光致发光量子效率（PLQY）。在二氯甲烷溶液中，Ir-R在732 nm（PLQY：24％）和Ir-OR在775 nm（PLQY：8％）处实现了更强的NIR发射。利用Ir-R作为磷光掺杂剂，以CBP为主体的固溶处理有机发光二极管（OLED）和以PVK：OXD-7为共主体的聚合物发光二极管（PLED）表现出出色的EL性能。在Ir-R中获得了最高的6
• Narrow-Band-Gap Conjugated Polymers Based on 2,7-Dioctyl-Substituted Dibenzo[<i>a,c</i>]phenazine Derivatives for Polymer Solar Cells
  作者：Ruifeng He、Lei Yu、Ping Cai、Feng Peng、Jin Xu、Lei Ying、Junwu Chen、Wei Yang、Yong Cao

  DOI：10.1021/ma500333r

  日期：2014.5.13

  A series of new 2,7-dioctyl-substituted dibenzo[a,c]phenazine (BPz) derivatives were designed and synthesized as electron-deficient units, which were copolymerized with an electron-rich indacenodithiophene (IDT) to construct narrow-bandgap copolymers PIDT-OHBPz, PIDT-OFBPz, and PIDT-OBPQ via Stale polycondensation. The 2,7-dioctyl substituents enhanced solubility and offered a new approach for developing various BPz derivatives. All copolymers showed high hole mobilities above 0.01 cm(2) V-1 s(-1) as measured by field effect transistors. The best performance of polymer solar cell was achieved based on PIDT-OFBPz with inverted device structure of ITO/ZnO/PFN/polymer:PC61BM/MoO3/Al, which showed an open-circuit voltage (V-oc) of 0.97 V, a short-circuit current (J(sc)) of 8.96 mA/cm(2), and a fill factor (FF) of 58.99%, leading to a high power conversion efficiency (PCE) of 5.13%. These results indicate that 2,7-alkyl-substituted BPz derivatives can be used as an excellent electron-deficient building block for the construction of high-performance organic electronic materials.
• Side chain effect on photovoltaic properties of dibenzo[a,c]phenazine based donor–acceptor polymers
  作者：Feng Peng、Baofeng Zhao、Jin Xu、Yuhao Zhang、Yiwen Fang、Ruifeng He、Hongbin Wu、Wei Yang、Yong Cao

  DOI：10.1016/j.orgel.2015.12.003

  日期：2016.2

  The electron donor polymers containing dibenzo[a,c]phenazine (BPz) derivatives with 2,7-alkyl and 11,12-alkoxy substituted, PBDT-BPzC and PBDT-OBPz, respectively, were synthesized to investigate the photovoltaic effect of different side chain substitutions. The polymers exhibit similar physical properties, except the HOMO and LUMO of PBDT-BPzC are 0.18 and 0.15 eV deeper than PBDT-OBPz, resulting in the V-oc of polymer solar cells (PSCs) based on PBDT-BPzC are above 0.1 V higher than that of PBDT-OBPz. With the contribution of the superior V-oc, polymer PBDT-BPzC showed preferable photovoltaic performances, and the PCE reached 4.44%, which is 0.49% higher than PBDT-OBPz. This research reveals a preferred side chain substituted way to modify BPz unit, and gives an optimally developing the dibenzo[a,c]phenazine derivatives based electron donor polymers. (C) 2015 Published by Elsevier B.V.