5,8-dibromo-2,3-bis(4-(octyloxy)phenyl)quinoxaline | 773094-62-5

• 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-2,3-bis(4-(octyloxy)phenyl)quinoxaline
• 英文别名: 2,3-bis(4-octyloxyphenyl)-5,8-dibromoquinoxaline；5,8-dibromo-2,3-bis(4-octoxyphenyl)quinoxaline
• CAS: 773094-62-5
• 化学式: C₃₆H₄₄Br₂N₂O₂
• 分子量: 696.566
• InChiKey: RSMXLZFJVYUNFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  42
• 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：
  4

反应信息

• 作为反应物：
  描述：

  5,8-dibromo-2,3-bis(4-(octyloxy)phenyl)quinoxaline 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 potassium acetate 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 2,3-bis(4-(octyloxy)phenyl)-5,8-bis(3-octylthiophen-2-yl)quinoxaline
  参考文献：
  名称：

  完全共轭的供体-受体-供体三嵌段共聚物的合成与表征

  摘要：

  建立一种合成方法以提供带有单个溴取代的端基的单官能远螯聚（3-辛基噻吩）（P3OT），其在制备明确的嵌段共聚物中具有潜在的用途。遥爪P3OT用催化剂转移缩聚5-溴-4-辛基-2-噻吩基由phenylnickel（II）引发剂引发的碘化物（CTCP）通过链生长工艺制备。淬灭反应的条件的优化允许在聚合物的末端安装α-溴官能团。我们通过将它定义为单官能聚合物Ph–P3OT–Br偶联到聚喹喔啉（PQ）带有硼酸酯末端基团，以提供新的一类供体-受体-供体（DA-D）三嵌段共聚物。三嵌段共聚物的形成通过凝胶渗透色谱法（GPC）和1 H NMR光谱法确认。使用紫外可见吸收和荧光光谱法研究了聚合物的光学性质。来自三嵌段共聚物的各个嵌段的荧光的有效猝灭与电子转移的发生是一致的。AFM图像说明了富电子的P3OT和贫电子的PQ块的纳米级相分离。

  DOI：

  10.1021/ma200084z
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 5,8-dibromo-2,3-bis(4-(octyloxy)phenyl)quinoxaline
  参考文献：
  名称：

  Synthesis and Characterization of Quinoxaline-Based Thiophene Copolymers as Photoactive Layers in Organic Photovoltaic Cells

  摘要：

  一系列基于喹喔啉的新型噻吩共聚物（PQx2T、PQx4T和PQx6T）通过Yamamoto和Stille偶联反应合成。PQx2T、PQx4T和PQx6T的$M_w$分别为20,000、12,000和29,000，多分散性指数分别为2.0、1.2和1.1。聚合物的紫外-可见吸收光谱显示在350 - 460 nm和560 - 600 nm范围内有两个明显的吸收峰，这源于寡噻吩单元的${\pi}-{\pi}^*$跃迁以及喹喔啉受体和噻吩供体之间的分子内电荷转移（ICT）。聚合物的HOMO能级范围为-5.37至-5.17 eV，LUMO能级范围为-3.67至-3.45 eV。PQx2T、PQx4T和PQx6T的电化学带隙分别为1.70、1.71和1.72 eV，因此表现出低带隙特性。当使用$PC_{71}BM$作为受体时，PQx2T、PQx4T和PQx6T的开路电压分别为0.58、0.42和0.47 V，短路电流密度分别为2.9、5.29和9.05 mA/$cm^2$。对于以PQx2T-PQx6T:$PC_{71}BM$（1:3）混合物为材料的太阳能电池，从PQx2T到PQx6T性能有所提升。在AM 1.5 G（100 mW/$cm^2$）光照下，PQx2T、PQx4T和PQx6T器件的功率转换效率分别为0.69%、0.73%和1.80%。

  DOI：

  10.5012/bkcs.2011.32.2.417

文献信息

• Unprecedented side reactions in Stille coupling: desired ones for Stille polycondensation
  作者：Hongyan Huang、Guanyuan Jiao、Shuli Liu、Quan Li、Xin Shi、Nina Fu、Lianhui Wang、Baomin Zhao、Wei Huang

  DOI：10.1039/c5cc05404d

  日期：——

  Unprecedented side reactions in Stille coupling: direct stannylation on the α-H of thiophene and stannylation of arylbromides via trialkylstanne halide.

  Stille偶联中前所未有的副反应：噻吩α-H的直接锡化和芳基溴化物经过三烷基锡卤化物的锡化。
• Synthesis and Characterization of Poly(5,8-quinoxaline ethynylene)s
  作者：Kathy B. Woody、Elizabeth M. Henry、Subodh Jagtap、David M. Collard

  DOI：10.1021/ma201347z

  日期：2011.12.13

  analogues. Here we report the synthesis and preliminary characterization of new class of electron-poor poly(arylene ethynylene)s (PAEs) that contain 5,8-quinoxaline ethynylene repeat units. While various PAE copolymers consisting of alternating electron-rich and electron-poor units display lower bandgaps than poly(phenylene ethynylene)s, the poly(5,8-quinoxaline ethynylene) (PQE) reported in this study

  大多数共轭有机聚合物是富含电子的材料，而电子贫乏（即电子接受）的类似物则少得多。在这里，我们报告的合成和初步表征的新型电子贫乏的聚（亚芳基乙炔）（PAEs）包含5,8-喹喔啉乙炔重复单元。尽管由富电子和贫电子的单元交替组成的各种PAE共聚物的带隙低于聚苯撑乙炔撑，但本研究报道的聚（5,8-喹喔啉乙炔撑）（PQE）具有较高的电子亲和力和较低的带隙（2.25 eV）高于许多这些供体-受体材料。与在喹喔啉之间没有乙炔键的聚（5,8-喹喔啉）（PQ）相比，PQE的吸收光谱发生了红移，这与共轭度更高的平面主链一致。此外，PQE的电化学还原电位比相应的PQ和含喹喔啉单元作为电子贫乏组分的供体-受体交替PAE共聚物都低。
• Organic polymer semiconductor, method of preparing the same, and ambipolar organic thin film transistor using the same
  申请人：Lee Bang Lin

  公开号：US20080099758A1

  公开（公告）日：2008-05-01

  Disclosed are an organic polymer semiconductor, an ambipolar organic thin film transistor using the same, an electronic device comprising the ambipolar organic thin film transistor and methods of fabricating the same. Example embodiments relate to an organic polymer semiconductor, which may include an aromatic ring derivative having p-type semiconductor properties and a heteroaromatic ring having n-type semiconductor properties in the main chain thereof, and which thus may exhibit both p-type transistor properties and n-type transistor properties when used in the organic active layer of an electronic device, e.g., an organic thin film transistor, an ambipolar organic thin film transistor using such an organic polymer semiconductor, an electronic device comprising the ambipolar organic thin film transistor and methods of fabricating the same.

  本发明涉及有机高分子半导体、使用该半导体的双极有机薄膜晶体管、包括该双极有机薄膜晶体管的电子设备以及制造它们的方法。例如实施例涉及一种有机高分子半导体，其可能包括在其主链中具有p型半导体性质的芳香环衍生物和具有n型半导体性质的杂环芳香环，并且因此在电子器件的有机活性层中使用时，可能同时表现出p型晶体管性质和n型晶体管性质，例如有机薄膜晶体管、使用此类有机高分子半导体的双极有机薄膜晶体管、包括该双极有机薄膜晶体管的电子设备以及制造它们的方法。
• Synthesis and Photovoltaic Properties of Quinoxaline-Based Alternating Copolymers for High-Efficiency Bulk-Heterojunction Polymer Solar Cells
  作者：Sang Kyu Lee、Woo-Hyung Lee、Jung Min Cho、Song Ju Park、Jin-Uk Park、Won Suk Shin、Jong-Cheol Lee、In-Nam Kang、Sang-Jin Moon

  DOI：10.1021/ma102943g

  日期：2011.8.9

  A series of quinoxaline-based copolymers, namely, poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-quinoxaline)] (P1), poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5- (5',8'-di-2-thienyl-2,3-bis (4-octyloxyl)phenyl)quinoxaline] (P2), and poly[N-9 ''-heptadecanyl-2,7-carbazole-alt-5,5-(5',8'-di-2-thienyl-2,3-bis(4-(3,7-dimethyloctyloxy)pheny)quinoxaline] (P3), were synthesized and characterized for use in polymer solar cells (PSCs). We describe the effect of modifying the alkyl group of the side chain of the quinoxaline derivatives on the electronic and optoelectronic properties of the polymers. The field-effect hole mobility as well as the electronic energy levels and processability of the materials for PSC applications were investigated. Among the studied quinoxaline-based copolymers, P2 showed the best photovoltaic performance with an open-circuit voltage (V(OC)) of 0.82 V, a short-circuit current density (J(SC)) of 9.96 mA/cm(2), a fill. factor (FF) of 0.49, and a power-conversion efficiency of 4.0% when a P2/PC(71)BM blend film was used as the active layer under AM 1.5 G irradiation (100 mW/cm(2)).
• Low bandgap EDOT-quinoxaline and EDOT-thiadiazol-quinoxaline conjugated polymers: Synthesis, redox, and photovoltaic device
  作者：Guobing Zhang、Yingying Fu、Qing Zhang、Zhiyuan Xie

  DOI：10.1016/j.polymer.2010.03.050

  日期：2010.5

  Three new low bandgap conjugated copolymers with 3,4-ethylenedioxythiophene (EDOT) as donor and 2,3-bis(4-octyloxyphenyl)-quinoxaline (P1), 2,3-bis(4-octyloxyphenyl)-thiadiazol-quinoxaline (P2, P3) as acceptors were synthesized by Stille cross-coupling reaction, and their optical and electrochemical properties were studied. These polymers exhibited optical bandgap of 1.77, 1.29 and 1.13 eV, for P1, P2 and P3, respectively. Photovoltaic cells with device configuration of ITO/PEDOT: PSS/Copolymer: PCBM (1:4 w/w)/LiF/Al were fabricated. The measurements revealed an open-circuit voltage (V-oc) of 0.52 V. short-circuit current density (J(sc)) of 3.24 mA/cm(2) and power conversion efficiency (PCE) of 0.60% for P1, and showed a V-OC of 0.33 V. J(sc) of 2.11 mA/cm(2), PCE of 0.39% for P2. (C) 2010 Elsevier Ltd. All rights reserved.