5,8-dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline | 1415800-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,8-dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline
• 英文别名: 5,8-Dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline；5,8-dibromo-6-fluoro-2,3-bis(3-octoxyphenyl)quinoxaline
• CAS: 1415800-22-4
• 化学式: C₃₆H₄₃Br₂FN₂O₂
• 分子量: 714.556
• InChiKey: NASRHGCEWPKBGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,8-dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 60.0h， 生成 5,8-bis(5-bromothiophen-2-yl)-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline
  参考文献：
  名称：

  Performance comparison of fluorinated and chlorinated donor–acceptor copolymers for polymer solar cells

  摘要：

  氯化可能是一种有效且简单的策略，用于开发高效的聚合物给体。

  DOI：

  10.1039/c8tc00948a
• 作为产物：
  描述：

  5-氟-4,7-二溴-[2,1,3]苯并噻二唑 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 5,8-dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline
  参考文献：
  名称：

  氟代喹喔啉化合物

  摘要：

  本发明属于有机化学领域，公开了一种氟代喹喔啉化合物，其化学通式如下式所示：该化合物由于在喹喔啉上引入强吸电特性的氟原子，因此能够降低材料的HOMO能级，从而提升聚合物光伏电池的开路电压。经循环伏安法测定本发明的化合物的HOMO能，与未氟代的喹喔啉衍生物相比，单氟代材料的HOMO能级比未氟代的材料低0.02～0.15eV，双氟代材料的HOMO能级比未氟代材料低0.05～0.3eV。该化合物可以作为聚合物光伏材料的中间体，用于制备性能优良的聚合物光活性材料。经循环伏安法测定化合物A～H的HOMO能，与未氟代的喹喔啉衍生物相比，单氟代材料的HOMO能级比未氟代的材料低0.02～0.15eV，双氟代材料的HOMO能级比未氟代材料低0.05～0.3eV。

  公开号：

  CN102827088B

文献信息

• 氟代喹喔啉化合物
  申请人：西安近代化学研究所

  公开号：CN102827088B

  公开（公告）日：2016-01-20

  本发明属于有机化学领域，公开了一种氟代喹喔啉化合物，其化学通式如下式所示：该化合物由于在喹喔啉上引入强吸电特性的氟原子，因此能够降低材料的HOMO能级，从而提升聚合物光伏电池的开路电压。经循环伏安法测定本发明的化合物的HOMO能，与未氟代的喹喔啉衍生物相比，单氟代材料的HOMO能级比未氟代的材料低0.02～0.15eV，双氟代材料的HOMO能级比未氟代材料低0.05～0.3eV。该化合物可以作为聚合物光伏材料的中间体，用于制备性能优良的聚合物光活性材料。经循环伏安法测定化合物A～H的HOMO能，与未氟代的喹喔啉衍生物相比，单氟代材料的HOMO能级比未氟代的材料低0.02～0.15eV，双氟代材料的HOMO能级比未氟代材料低0.05～0.3eV。
• Synthesis and photovoltaic properties of an alternating polymer based fluorene and fluorine substituted quinoxaline derivatives
  作者：Haimei Wu、Bo Qu、Di Tian、Zhiyuan Cong、Bowen Gao、Jianqun Liu、Zhongwei An、Chao Gao、Lixin Xiao、Zhijian Chen、Qihuang Gong、Wei Wei

  DOI：10.1016/j.reactfunctpolym.2013.07.015

  日期：2013.11

  An alternating polymer (PFOFTQx) with 9,9-dioctylfluorene (FO) as electron-rich unit and fluorine substituted quinoxaline (FTQx) as electron-withdrawing unit was synthesized and characterized. PFOFTQx showed similar absorption property with that of the counterpart polymer without fluorine atom (synthesized APFO-15). However, the low-lying highest occupied molecular orbit (HOMO) energy level of PFOFTQx was -5.37 eV, about 0.07 eV smaller than that of synthesized APFO-15. In order to study the photovoltaic properties of the materials, polymer solar cells (PSCs) were fabricated with PFOFTQx as donor blended with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor. The power conversion efficiency (PCE) of PSC was 1.77% with a high open-circuit voltage (V-oc) of 0.90 V for an optimized PFOFTQx:PC61BM weight ratio of 1:5, in comparison with that of synthesized APFO-15-based device (PCE of 1.60% with V-oc of 0.77 V). This study indicated that fluorine substituted quinoxaline-based polymers would be promising material with a higher V-oc for the application in polymer solar cells. (C) 2013 Elsevier Ltd. All rights reserved.
• Performance comparison of fluorinated and chlorinated donor–acceptor copolymers for polymer solar cells
  作者：Yubao Zhang、Fumeng Ren、Qinghua Li、Zhixuan Zhang、Xingdao He、Zhongping Chen、Jiulin Shi、Guoli Tu

  DOI：10.1039/c8tc00948a

  日期：——

  Chlorination could be an effective and simple strategy to develop highly efficient polymer donors.

  氯化可能是一种有效且简单的策略，用于开发高效的聚合物给体。
• Side-Chain Engineering of Benzodithiophene-Fluorinated Quinoxaline Low-Band-Gap Co-polymers for High-Performance Polymer Solar Cells
  作者：Xiaopeng Xu、Yulei Wu、Junfeng Fang、Zuojia Li、Zhenguo Wang、Ying Li、Qiang Peng

  DOI：10.1002/chem.201403153

  日期：2014.10.6

  AbstractA new series of donor–acceptor co‐polymers based on benzodithiophene and quinoxaline with various side chains have been developed for polymer solar cells. The effect of the degree of branching and dimensionality of the side chains were systematically investigated on the thermal stability, optical absorption, energy levels, molecular packing, and photovoltaic performance of the resulting co‐polymers. The results indicated that the linear and 2D conjugated side chains improved the thermal stabilities and optical absorptions. The introduction of alkylthienyl side chains could efficiently lower the energy levels compared with the alkoxyl‐substituted analogues, and the branched alkoxyl side chains could deepen the HOMO levels relative to the linear alkoxyl chains. The branched alkoxyl groups induced better lamellar‐like ordering, but poorer face‐to‐face packing behavior. The 2D conjugated side chains had a negative influence on the crystalline properties of the co‐polymers. The performance of the devices indicated that the branched alkoxyl side chains improved the Voc, but decreased the Jsc and fill factor (FF). However, the 2D conjugated side chains would increase the Voc, Jsc, and FF simultaneously. For the first time, our work provides insight into molecular design strategies through side‐chain engineering to achieve efficient polymer solar cells by considering both the degree of branching and dimensionality.