2,3-di(2-furyl)-5,8-bis(2-(3-methoxythiophene))quinoxaline

• 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-di(2-furyl)-5,8-bis(2-(3-methoxythiophene))quinoxaline
• 英文别名: 2,3-Bis(furan-2-yl)-5,8-bis(3-methoxythiophen-2-yl)quinoxaline；2,3-bis(furan-2-yl)-5,8-bis(3-methoxythiophen-2-yl)quinoxaline
• 化学式: C₂₆H₁₈N₂O₄S₂
• 分子量: 486.572
• InChiKey: SHCNLVNPUREETF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2'-联糠醛 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(ll) sulfate pentahydrate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.5h， 生成 2,3-di(2-furyl)-5,8-bis(2-(3-methoxythiophene))quinoxaline
  参考文献：
  名称：

  The synthesis of new donor–acceptor polymers containing the 2,3-di(2-furyl) quinoxaline moiety: Fast-switching, low-band-gap, p- and n-dopable, neutral green-colored materials

  摘要：

  Three donor-acceptor type pi-conjugated polymers were synthesized electrochemically: poly[2,3-di(2-furyl)-5,8-bis(2-(3,4-ethylenedioxythiophene)) quinoxaline] (PFETQ), poly[2,3-di(2-furyl)-5,8-bis(2-thienyl) quinoxaline] (PFTQ) and poly[2,3-di(2-furyl)-5,8-bis(2-(3-methoxythiophene)) quinoxaline] (PFMTQ). All of the synthesized polymers, contained the 2,3-di(2-furyl) quinoxaline moiety in the backbone as the acceptor unit and different thiophene derivatives as the donor units. The electroactivity of the monomers and the electrochemical properties of their polymers were investigated by cyclic voltammetry. The presence of the strong electron-donating ethylenedioxy and methoxy groups on the aromatic structure increased the electron density. Thus, the oxidation potential of FETQ and FMTQ shifted to a lower value than that of FTQ. The optical properties of the polymers were investigated by UV-vis-NIR spectroscopy. Both PFETQ and PFMTQ reveal two distinct absorption bands in the red and blue regions of the visible spectrum, while PFTQ has only one dominant wavelength at 596 nm in the visible region. The colorimetry analysis revealed that while PFTQ has a light blue color, PFETQ and PFMTQ are green in the neutral state. The optical band gaps, defined as the onset of the pi-pi* transition, were found to be 1.15 eV for PFETQ, 1.2 eV for PFMTQ and 1.34 eV for PFTQ. Moreover, all three polymers showed both n-doping and fast switching times. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2015.02.033

文献信息

• The synthesis of new donor–acceptor polymers containing the 2,3-di(2-furyl) quinoxaline moiety: Fast-switching, low-band-gap, p- and n-dopable, neutral green-colored materials
  作者：Zhen Xu、Min Wang、Weiyu Fan、Jinsheng Zhao、Huaisheng Wang

  DOI：10.1016/j.electacta.2015.02.033

  日期：2015.4

  Three donor-acceptor type pi-conjugated polymers were synthesized electrochemically: poly[2,3-di(2-furyl)-5,8-bis(2-(3,4-ethylenedioxythiophene)) quinoxaline] (PFETQ), poly[2,3-di(2-furyl)-5,8-bis(2-thienyl) quinoxaline] (PFTQ) and poly[2,3-di(2-furyl)-5,8-bis(2-(3-methoxythiophene)) quinoxaline] (PFMTQ). All of the synthesized polymers, contained the 2,3-di(2-furyl) quinoxaline moiety in the backbone as the acceptor unit and different thiophene derivatives as the donor units. The electroactivity of the monomers and the electrochemical properties of their polymers were investigated by cyclic voltammetry. The presence of the strong electron-donating ethylenedioxy and methoxy groups on the aromatic structure increased the electron density. Thus, the oxidation potential of FETQ and FMTQ shifted to a lower value than that of FTQ. The optical properties of the polymers were investigated by UV-vis-NIR spectroscopy. Both PFETQ and PFMTQ reveal two distinct absorption bands in the red and blue regions of the visible spectrum, while PFTQ has only one dominant wavelength at 596 nm in the visible region. The colorimetry analysis revealed that while PFTQ has a light blue color, PFETQ and PFMTQ are green in the neutral state. The optical band gaps, defined as the onset of the pi-pi* transition, were found to be 1.15 eV for PFETQ, 1.2 eV for PFMTQ and 1.34 eV for PFTQ. Moreover, all three polymers showed both n-doping and fast switching times. (C) 2015 Elsevier Ltd. All rights reserved.