1-{4-[(2,5-bis-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl)methoxy]phenyl}-2-phenyldiazene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 1-{4-[(2,5-bis-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl)methoxy]phenyl}-2-phenyldiazene
• 英文别名: [4-[[2,5-Bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl]methoxy]phenyl]-phenyldiazene；[4-[[2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl]methoxy]phenyl]-phenyldiazene
• 化学式: C₂₉H₂₂N₂O₅S₃
• 分子量: 574.702
• InChiKey: ICWPFALHELBECR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-N-苯基苯酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成 1-{4-[(2,5-bis-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl)methoxy]phenyl}-2-phenyldiazene
  参考文献：
  名称：

  Electrochemical and spectroelectrochemical studies of poly(2,5-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-ylthienyl) derivatives bearing azobenzene, coumarine and fluorescein dyes: Effect of chromophore groups on electrochromic properties

  摘要：

  Three novel thiophene based monomers, 2,5-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-ylthienyl derivatives, 1-{4-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy] phenyl}-2-phenyldiazene) (ETEAz), 4-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy]2H- chromen-2-one) (ETECo) and methyl 2-{6-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy]-3-oxo-3H-xanthen -9-yl} benzoate (ETEFlo), were synthesized and their conducting polymers were electrochemically prepared on ITO glass electrodes for the first time. The electroactive monomers were functionalized with strong chromophore groups such as azobenzene, coumarine and fluorescein in order to investigate the effect of chromophore units on electrochemical and spectroelectrochemical characteristics of corresponding conducting polymers. Spectroelectrochemical studies demonstrated that combination of a strong chromophore group with polymer backbone leads to significant changes in electronic and optoelectronic behaviors of resulting conducting polymers. PETEAz, PETECo and PETEFlo exhibited multicolored electrochromism with three distinct states. PETEAz revealed 33% (565 nm) and 52% (1270 nm) transmittance changes (Delta T%), while PETECo exhibited 40% (535 nm) and 64% (1245 nm) at their dominant wavelenghts. The optical contrasts of PETEFlo were measured as 15% (495 nm), 28% (560 nm) and 43% (1345 nm), which were lower than those of PETEAz and PETEFlo. It was observed that all conducting polymer films could be very quickly switched between their neutral and oxidized states in both visible and NIR regions. Switching times values were found to be 0.3 s at 565 nm and 0.4 s at 1270 nm for PETEAz, 0.4 s at 535 nm and 0.5 s at 1245 nm for PETECo, 0.4 s at 495 nm, 0.4 s at 560 nm and 0.7 s at 1345 nm. Moreover, the optical band gap values for PETEAz, PETECo and PETEFIo were calculated as 1.6 eV, 1.4 eV and 1.55 eV, respectively, from the onset of pi-pi* transition in polymer films' neutral states. a 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2014.09.053

文献信息

• Electrochemical and spectroelectrochemical studies of poly(2,5-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-ylthienyl) derivatives bearing azobenzene, coumarine and fluorescein dyes: Effect of chromophore groups on electrochromic properties
  作者：Deniz Yiğit、Yasemin Arslan Udum、Mustafa Güllü、Levent Toppare

  DOI：10.1016/j.electacta.2014.09.053

  日期：2014.11

  Three novel thiophene based monomers, 2,5-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-ylthienyl derivatives, 1-4-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy] phenyl}-2-phenyldiazene) (ETEAz), 4-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy]2H- chromen-2-one) (ETECo) and methyl 2-6-[(2,5-Di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-3-thienyl) methoxy]-3-oxo-3H-xanthen -9-yl} benzoate (ETEFlo), were synthesized and their conducting polymers were electrochemically prepared on ITO glass electrodes for the first time. The electroactive monomers were functionalized with strong chromophore groups such as azobenzene, coumarine and fluorescein in order to investigate the effect of chromophore units on electrochemical and spectroelectrochemical characteristics of corresponding conducting polymers. Spectroelectrochemical studies demonstrated that combination of a strong chromophore group with polymer backbone leads to significant changes in electronic and optoelectronic behaviors of resulting conducting polymers. PETEAz, PETECo and PETEFlo exhibited multicolored electrochromism with three distinct states. PETEAz revealed 33% (565 nm) and 52% (1270 nm) transmittance changes (Delta T%), while PETECo exhibited 40% (535 nm) and 64% (1245 nm) at their dominant wavelenghts. The optical contrasts of PETEFlo were measured as 15% (495 nm), 28% (560 nm) and 43% (1345 nm), which were lower than those of PETEAz and PETEFlo. It was observed that all conducting polymer films could be very quickly switched between their neutral and oxidized states in both visible and NIR regions. Switching times values were found to be 0.3 s at 565 nm and 0.4 s at 1270 nm for PETEAz, 0.4 s at 535 nm and 0.5 s at 1245 nm for PETECo, 0.4 s at 495 nm, 0.4 s at 560 nm and 0.7 s at 1345 nm. Moreover, the optical band gap values for PETEAz, PETECo and PETEFIo were calculated as 1.6 eV, 1.4 eV and 1.55 eV, respectively, from the onset of pi-pi* transition in polymer films' neutral states. a 2014 Elsevier Ltd. All rights reserved.