5,8-dibromo-2,3-dihexylquinoxaline

• 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-dihexylquinoxaline
• 化学式: C₂₀H₂₈Br₂N₂
• 分子量: 456.264
• InChiKey: KBZPMDSEBGYOLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,8-dibromo-2,3-dihexylquinoxaline 在 四(三苯基膦)钯 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 27.0h， 生成 5-(2,3-dihexyl-8-(thiophen-2-yl)quinoxalin-5-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  D–π–A–π–A featured dyes containing different electron-withdrawing auxiliary acceptors: The impact on photovoltaic performances

  摘要：

  Four novel D-pi-A-pi-A metal-free organic dyes Q1-Q4 were synthesized and the impacts of the auxiliary acceptors on the photovoltaic performances were studied. Q2 with quinoxaline as the auxiliary acceptor exhibited the best photovoltaic performance due to its highest short-circuit photocurrent density (17.22 mA cm(-2)), leading to a power conversion efficiency of 7.42% under simulated AM 1.5 G illumination. Q1 with the strongest electron withdrawing group (pyrazino[2,3-gjquinoxaline) as the auxiliary acceptor showed the weakest performance, which can be attributed to electron trap and mismatch of energy-level. The results showed that the different electron-withdrawing property of auxiliary units significantly influenced the absorption, energy levels and photovoltaic performance. Incorporating auxiliary acceptor with moderate electron-deficient ability can extend the absorption range and adjust the molecular orbital energy levels, resulting in better photovoltaic performance. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.04.001
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 氢溴酸 、 溴 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5,8-dibromo-2,3-dihexylquinoxaline
  参考文献：
  名称：

  聚（2,3-二己基噻吩并[3,4-b]吡嗪-alt-2,3-二己基喹喔啉）：通过直接芳基化聚合的可加工、低带隙、双极性受体框架

  摘要：

  报道了一种新的二烷基官能化喹喔啉受体 5,8-二溴-2,3-二己基喹喔啉的合成，以及它与 2,3-二己基噻吩并 [3,4-b] 吡嗪通过直接芳基化聚合的交叉偶联. 所得双极性受体聚合物聚 (2,3-二己基噻吩并 [3,4-b] 吡嗪-alt-2,3-二己基喹喔啉) 具有 1.07 eV 的低带隙和高溶解度。还报告了初始有机光伏器件的结果。

  DOI：

  10.1055/s-0037-1610299

文献信息

• Luminescent solar concentrators with outstanding optical properties by employment of D–A–D quinoxaline fluorophores
  作者：Costanza Papucci、Rima Charaf、Carmen Coppola、Adalgisa Sinicropi、Mariangela di Donato、Maria Taddei、Paolo Foggi、Antonella Battisti、Bastiaan de Jong、Lorenzo Zani、Alessandro Mordini、Andrea Pucci、Massimo Calamante、Gianna Reginato

  DOI：10.1039/d1tc02923a

  日期：——

  use in building-integrated photovoltaics (BIPV). The optimization of LSC performances involves the adjustment of both the fluorophore and the guest polymer matrix. On this account, we investigated a series of high quantum yield, donor–acceptor–donor (D–A–D) photostable fluorophores (DQ1–5), presenting a central quinoxalinic acceptor core, not previously employed in LSCs, and triarylamines or phenothiazine

  发光太阳能聚光器 (LSC) 是旨在有效收集直接和漫射太阳辐射并将其集中在光伏电池上以促进其在建筑集成光伏 (BIPV) 中使用的设备。LSC 性能的优化涉及荧光团和客体聚合物基质的调整。为此，我们研究了一系列高量子产率、供体-受体-供体（D-A-D）光稳定荧光团（DQ1-5)，呈现一个中央喹喔啉受体核心，以前未在 LSC 中使用，以及三芳胺或吩噻嗪作为供体基团。这些分子还在中央核心和/或供体基团上用烷基链装饰，以探索它们与本研究中使用的聚（甲基丙烯酸甲酯）（PMMA）和聚（甲基丙烯酸环己酯）（PCMA）基质的相容性。PMMA 和 PCMA 薄膜（25 μm 厚），含有 0.2–2.2 wt% 的DQ1–5，在 370–550 nm 范围内吸收并在 550–600 nm 处呈现最大发射，即使在兴奋剂含量最高。值得注意的是，DQ1 /PMMA 薄膜表现出增强的相位兼容性和优异的量子产率，即,
• MULTI-COLORED CONJUGATED POLYMERS WITH HIGHLY TRANSMISSIVE OXIDIZED STATE
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP2571920A2

  公开（公告）日：2013-03-27
• US8450449B2
  申请人：——

  公开号：US8450449B2

  公开（公告）日：2013-05-28
• [EN] MULTI-COLORED CONJUGATED POLYMERS WITH HIGHLY TRANSMISSIVE OXIDIZED STATE<br/>[FR] POLYMÈRES CONJUGUÉS MULTICOLORES AVEC ÉTAT OXYDÉ À TRANSMISSION ÉLEVÉE
  申请人：UNIV FLORIDA

  公开号：WO2012021195A2

  公开（公告）日：2012-02-16

  Embodiments of the invention are directed to random conjugated copolymers comprising a plurality of one or more different donor (D) repeating units and a plurality of at least one acceptor (A) repeating unit. At least one of the D units has a solubilizing substituent, statistically a portion of the A repeating units are separated from each other by only one D units and a plurality of the A unit are adjacent to one the D units having the solubilizing substituents. The random conjugated copolymers are black or colored in the neutral state and highly transmissive in the oxidized state. The random conjugated copolymers have the structure -[(D)xA]n-, where x > 1 and n(x+l) ≥ 10 or the structure - [(DA)x-(D'A)y]n-, where D represents one substituted D unit and D' represents another D units and where x ≥ 1, y ≥ 1 and 2n(x+y) ≥ 10. Other embodiments of the invention are directed to forming the -[(D)xA]n- or -[(DA)x-(D'A)y]n- random conjugated copolymers by condensation polymerizations between monomers containing complementary reactive groups.
• Poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline): Processible, Low-Bandgap, Ambipolar-Acceptor Frameworks via Direct Arylation Polymerization
  作者：Seth Rasmussen、Trent Anderson、Evan Culver、Furqan Almyahi、Paul Dastoor

  DOI：10.1055/s-0037-1610299

  日期：2018.12

  The synthesis of a new dialkyl-functionalized quinoxaline ­acceptor, 5,8-dibromo-2,3-dihexylquinoxaline, is reported, along with its cross-coupling with 2,3-dihexylthieno[3,4-b]pyrazine via direct arylation polymerization. The resulting ambipolar-acceptor polymer ­poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline) exhib­its a low bandgap of 1.07 eV and high solubility. The results of

  报道了一种新的二烷基官能化喹喔啉受体 5,8-二溴-2,3-二己基喹喔啉的合成，以及它与 2,3-二己基噻吩并 [3,4-b] 吡嗪通过直接芳基化聚合的交叉偶联. 所得双极性受体聚合物聚 (2,3-二己基噻吩并 [3,4-b] 吡嗪-alt-2,3-二己基喹喔啉) 具有 1.07 eV 的低带隙和高溶解度。还报告了初始有机光伏器件的结果。