1,2-bis(3-hexyloxyphenyl)ethane-1,2-dione | 1416047-41-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(3-hexyloxyphenyl)ethane-1,2-dione
• 英文别名: bis-(3-hexyloxyphenyl)ethane-1,2-dione；1,2-Bis(3-(hexyloxy)phenyl)ethane-1,2-dione；1,2-bis(3-hexoxyphenyl)ethane-1,2-dione
• CAS: 1416047-41-0
• 化学式: C₂₆H₃₄O₄
• 分子量: 410.554
• InChiKey: TUOQUVOSOCOHQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(3-hexyloxyphenyl)ethane-1,2-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 60.0h， 生成 6,7-Difluoro-2,3-bis(3-(hexyloxy)phenyl)-5,8-di(thiophen-2-yl)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
• 作为产物：
  描述：

  溴己烷 在 正丁基锂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,2-bis(3-hexyloxyphenyl)ethane-1,2-dione
  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

• 低分子化合物、高分子化合物、これらの合成方法、及び、有機半導体材料
  申请人：国立大学法人広島大学

  公开号：JP2018145125A

  公开（公告）日：2018-09-20

  【課題】所望の分子軌道エネルギー準位に制御し得る設計自由度を有する低分子化合物、高分子化合物、これらの合成方法、及び、有機半導体材料の提供。【解決手段】式１で表される低分子化合物。（Ｙ１及びＹ２は夫々独立にＨ、ハロゲン又は、置換／非置換の１つ以上の複素芳香環；ｍは１又は２；Ｘ１及びＸ２は夫々独立して式１１〜式１４で表される基；Ｒは夫々独立して置換／非置換のアルキル基、アルコキシ基、エステル基、アシル基、芳香環又は複素芳香環）【選択図】図２

  这是一篇关于低分子化合物和高分子化合物的设计和合成方法，旨在控制所需分子轨道能级，并提供有机半导体材料。解决方案是低分子化合物，由公式1表示。（其中Y1和Y2是各自独立的H、卤素或一个或多个取代/非取代的复杂芳香环；m为1或2；X1和X2是各自独立的由公式11至14表示的基；R是各自独立的取代/非取代的烷基、烷氧基、酯基、酰基、芳香环或复杂芳香环）。【选择图】图2。
• 10.1002/jhet.4828
  作者：Tedder, Mariah L.、Carrick, Jesse D.

  DOI：10.1002/jhet.4828

  日期：——

  improved separations performance, a synthetic method to construct various alkoxy-complexant derivatives was required. In this work, a convergent synthetic strategy for the production of 3,3′- and 4,4′-tetraalkoxy-bis-1,2,4-triazinyl-2,6-pyridines from readily available starting materials via a dealkylation/alkylation/condensation approach is described. Synthetic method development, substrate scope

  杂芳基-1,2,4-三嗪络合剂通常用于分离科学中，用于选择性螯合模拟高放废物中 Ln 中的少量 An。为了促进获得相关化学实体以进行假设驱动的探究以提高分离性能，需要一种构建各种烷氧基络合剂衍生物的合成方法。在这项工作中，采用了一种聚合合成策略，通过脱烷基化/烷基化从易于获得的起始原料中生产 3,3'- 和 4,4'-四烷氧基-双-1,2,4-三嗪基-2,6-吡啶描述了/condensation 方法。本文报道了各种工艺相关稀释剂中的合成方法开发、底物范围、初步溶解度和水解稳定性数据。
• 一种含有稠环结构的共轭小分子半导体材料及其应用
  申请人：南方科技大学

  公开号：CN116496291A

  公开（公告）日：2023-07-28

  本发明公开了一种含有稠环结构的共轭小分子半导体材料及其应用，所述含有稠环结构的共轭小分子半导体材料具有受体‑给体‑受体结构；所述含有稠环结构的共轭小分子半导体材料的结构式为该含有稠环结构的共轭小分子半导体材料具有重复的受体‑给体‑受体单元和长吸收的特征，采用该共轭小分子半导体材料作为活性层的光探测器器件可以有效将响应波长从可见光延申至近红外区域，提高了有机光探测器在近红外波段响应的灵敏度。
• 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.
• Synthetic approach to the construction of unsymmetric pyridyl-1,2,4-triazine complexants
  作者：Eric A. Agyei、Jesse D. Carrick

  DOI：10.1016/j.tet.2024.133872

  日期：2024.4