5,8-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(3-(hexyloxy)phenyl)quinoxaline | 1416047-44-3

• 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-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(3-(hexyloxy)phenyl)quinoxaline
• 英文别名: 5,8-Bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(3-(hexyloxy)phenyl)quinoxaline；5,8-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(3-hexoxyphenyl)quinoxaline
• CAS: 1416047-44-3
• 化学式: C₄₀H₃₈Br₂F₂N₂O₂S₂
• 分子量: 840.691
• InChiKey: LHZOONDTPDMAQE-UHFFFAOYSA-N

物化性质

• 沸点：
  738.3±55.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,2-二氟苯 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸 、 溴 、 硝酸 、 铁粉 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 80.0h， 生成 5,8-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(3-(hexyloxy)phenyl)quinoxaline
  参考文献：
  名称：

  Quinoxaline-Based Polymer Dots with Ultrabright Red to Near-Infrared Fluorescence for In Vivo Biological Imaging

  摘要：

  This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polymer backbones and systematically investigated their effect on the fluorescence quantum yields of Pdots. These new series of quinoxaline-based Pdots have a fluorescence quantum yield as high as 47% with a Stokes shift larger than 150 nm. Single-particle analysis reveals that the average per-particle brightness of the Pdots is at least 6 times higher than that of the commercially available quantum dots. We further demonstrated the use of this new class of quinoxaline-based Pdots for effective and specific cellular and subcellular labeling without any noticeable nonspecific binding. Moreover, the cytotoxicity of Pdots were evaluated on HeLa cells and zebrafish embryos to demonstrate their great biocompatibility. By taking advantage of their extreme brightness and minimal cytotoxicity, we performed, for the first time, in vivo microangiography imaging on living zebrafish embryos using Pdots. These quinoxaline-based NIR-fluorescent Pdots are anticipated to find broad use in a variety of in vitro and in vivo biological research.

  DOI：

  10.1021/jacs.5b06710

文献信息

• Prominent Short-Circuit Currents of Fluorinated Quinoxaline-Based Copolymer Solar Cells with a Power Conversion Efficiency of 8.0%
  作者：Hsieh-Chih Chen、Ying-Hsiao Chen、Chi-Chang Liu、Yun-Chen Chien、Shang-Wei Chou、Pi-Tai Chou

  DOI：10.1021/cm302861s

  日期：2012.12.21

  A tailor-made medium-band gap fluorinated quinoxaline-based conjugated polymer of PBDT-TFQ was designed and synthesized as a donor material for bulk-heterojunction (BHJ) solar cells. This polymer is possessed of an intrachain donor-acceptor architecture and exhibits a broad and strong absorption spectrum across the entire UV-vis region. The introduction of F atoms with high electron affinity to the quinoxaline moiety is effective in further lowering both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of PBDT-TFQ to attain higher open-circuit voltage (V-oc). With an optimized blend ratio of PBDT-TFQ:PC71BM (1:1, w/w), a high power conversion efficiency (PCE) of 8.0% was obtained, with a V-oc of 0.76 V, a short-circuit current density (J(sc)) of 18.2 mA cm(-2), and a fill factor (FF) of 58.1% under AM 1.5G irradiation. The resulting copolymer reveals an outstanding J(sc) value, arising from the higher hole mobility of PBDT-TFQ together with the better continuous percolation pathways within the polymer blend for efficient exciton dissociation and charge transport.
• Semiconductor Compound, Use Thereof and Hydrogen Production System
  申请人：National Tsing Hua University

  公开号：US20200407491A1

  公开（公告）日：2020-12-31

  The present disclosure provides a semiconductor compound, which includes a metal complex unit and a conjugate unit. The metal complex unit includes a coordination center and a plurality of ligands. The coordination center is a metal ion or a metal atom, and the ligands are linked with the coordination center. The conjugate unit is linked with the metal complex unit by covalent bond.
• Quinoxaline-Based Polymer Dots with Ultrabright Red to Near-Infrared Fluorescence for In Vivo Biological Imaging
  作者：Hong-Yi Liu、Pei-Jing Wu、Shih-Yu Kuo、Chuan-Pin Chen、En-Hao Chang、Chang-Yi Wu、Yang-Hsiang Chan

  DOI：10.1021/jacs.5b06710

  日期：2015.8.19

  This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polymer backbones and systematically investigated their effect on the fluorescence quantum yields of Pdots. These new series of quinoxaline-based Pdots have a fluorescence quantum yield as high as 47% with a Stokes shift larger than 150 nm. Single-particle analysis reveals that the average per-particle brightness of the Pdots is at least 6 times higher than that of the commercially available quantum dots. We further demonstrated the use of this new class of quinoxaline-based Pdots for effective and specific cellular and subcellular labeling without any noticeable nonspecific binding. Moreover, the cytotoxicity of Pdots were evaluated on HeLa cells and zebrafish embryos to demonstrate their great biocompatibility. By taking advantage of their extreme brightness and minimal cytotoxicity, we performed, for the first time, in vivo microangiography imaging on living zebrafish embryos using Pdots. These quinoxaline-based NIR-fluorescent Pdots are anticipated to find broad use in a variety of in vitro and in vivo biological research.