2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-dithien-2-ly)quinoxaline | 1021849-53-5

• 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: 2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-dithien-2-ly)quinoxaline
• 英文别名: 2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromodithien-2-yl)quinoxaline；5,8-Bis(5-bromothiophen-2-yl)-2,3-bis(4-(octyloxy)phenyl)quinoxaline；5,8-bis(5-bromothiophen-2-yl)-2,3-bis(4-octoxyphenyl)quinoxaline
• CAS: 1021849-53-5
• 化学式: C₄₄H₄₈Br₂N₂O₂S₂
• 分子量: 860.817
• InChiKey: MBNYPTOZUUJCRR-UHFFFAOYSA-N

物化性质

• 沸点：
  786.3±60.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-dithien-2-ly)quinoxaline 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 甲基三辛基氯化铵 、 sodium carbonate 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-4'-hexyl-2,2'-bithiophene-5-ly)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
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 生成 2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-dithien-2-ly)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

• 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)).
• Synthesis and Photovoltaic Properties of a Low-Band-Gap Copolymer of Dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]thiophene and Dithienylquinoxaline
  作者：Abasaheb V. Patil、Woo-Hyung Lee、Eunwoo Lee、Kyuri Kim、In-Nam Kang、Soo-Hyoung Lee

  DOI：10.1021/ma102722d

  日期：2011.3.22
• US8354666B2
  申请人：——

  公开号：US8354666B2

  公开（公告）日：2013-01-15
• Synthesis and Characterization of Quinoxaline-Based Thiophene Copolymers as Photoactive Layers in Organic Photovoltaic Cells
  作者：Yoon-Suk Choi、Woo-Hyung Lee、Jae-Ryoung Kim、Sang-Kyu Lee、Won-Suk Shin、Sang-Jin Moon、Jong-Wook Park、In-Nam Kang

  DOI：10.5012/bkcs.2011.32.2.417

  日期：2011.2.20

  A series of new quinoxaline-based thiophene copolymers (PQx2T, PQx4T, and PQx6T) was synthesized via Yamamoto and Stille coupling reactions. The $M_ws$ of PQx2T, PQx4T, and PQx6T were found to be 20,000, 12,000, and 29,000, with polydispersity indices of 2.0, 1.2, and 1.1, respectively. The UV-visible absorption spectra of the polymers showed two distinct absorption peaks in the ranges 350 - 460 nm and 560 - 600 nm, which arose from the $\pi}-\pi}^*$ transition of oligothiophene units and intramolecular charge transfer (ICT) between a quinoxaline acceptor and thiophene donor. The HOMO levels of the polymer ranged from -5.37 to -5.17 eV and the LUMO levels ranged from -3.67 to -3.45 eV. The electrochemical bandgaps of PQx2T, PQx4T, and PQx6T were 1.70, 1.71, and 1.72 eV, respectively, thus yielding low bandgap behavior. PQx2T, PQx4T, and PQx6T had open circuit voltages of 0.58, 0.42, and 0.47 V, and short circuit current densities of 2.9, 5.29 and 9.05 mA/$cm^2$, respectively, when $PC_71}BM$ was used as an acceptor. For the solar cells with PQx2T-PQx6T:$PC_71}BM$ (1:3) blends, an increase in performance was observed in going from PQx2T to PQx6T. The power conversion efficiencies of PQx2T, PQx4T, and PQx6T devices were found to be 0.69%, 0.73%, and 1.80% under AM 1.5 G (100 mW/$cm^2$) illumination.

  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%。