3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene] | 1370227-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene]
• 英文别名: 3',6'-Dioctoxy-2,7-dithiophen-2-ylspiro[fluorene-9,9'-xanthene]；3',6'-dioctoxy-2,7-dithiophen-2-ylspiro[fluorene-9,9'-xanthene]
• CAS: 1370227-80-7
• 化学式: C₄₉H₅₂O₃S₂
• 分子量: 753.082
• InChiKey: ZHZFYLHVPAQPEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,7-dibromo-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene] 、 2-(tributylstannyl)thiophene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 以35%的产率得到3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene]
  参考文献：
  名称：

  New fluorene–xanthene-based hybrid electrochromic and fluorescent polymers via donor–acceptor approach

  摘要：

  Two novel donor-acceptor type, spiro-configured, fluorene derivatives 3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene] (TXT) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-3',6'-bis(octyloxy)spiro[fluorene-9,9'-xanthene] (EXE) have been synthesized and then electropolymerized via potentiodynamic and potentiostatic methods.Optical and electrochemical properties of their polymers, poly(3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene]) (PTXT) and poly(2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)3',6'-bis(octyloxy)spiro[fluorene-9,9'-xanthene]) (PEXE) were investigated and it was found that polymers exhibit reversible redox behavior (Eonset-Oxd = 0.85 V for PTXT, Eonset-Oxd = 0.08 V for PEXE) accompanied with a reversible electrochromic behavior, yellow to green for FTXT, scarlet red to turquoise green with different intermediate colors for PEXE. The band gaps of the polymers were found to be 2.23 eV and 1.74 eV for PTXT and PEXE, respectively. PTXT was also prepared via chemical polymerization and the obtained polymer was found to display blue light emission in chloroform with a relatively high quantum yield (Phi(f) = 0.59 in cyclohexane) despite having bluish-green light emission in the solid state. Both PTXT and PEXE are thermally stable with decomposition temperatures above 300 degrees C. (C)12 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2012.01.026

文献信息

• New fluorene–xanthene-based hybrid electrochromic and fluorescent polymers via donor–acceptor approach
  作者：Buket Bezgin Carbas、Ahmet M. Önal

  DOI：10.1016/j.electacta.2012.01.026

  日期：2012.4

  Two novel donor-acceptor type, spiro-configured, fluorene derivatives 3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene] (TXT) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-3',6'-bis(octyloxy)spiro[fluorene-9,9'-xanthene] (EXE) have been synthesized and then electropolymerized via potentiodynamic and potentiostatic methods.Optical and electrochemical properties of their polymers, poly(3',6'-bis(octyloxy)-2,7-di(thiophen-2-yl)spiro[fluorene-9,9'-xanthene]) (PTXT) and poly(2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)3',6'-bis(octyloxy)spiro[fluorene-9,9'-xanthene]) (PEXE) were investigated and it was found that polymers exhibit reversible redox behavior (Eonset-Oxd = 0.85 V for PTXT, Eonset-Oxd = 0.08 V for PEXE) accompanied with a reversible electrochromic behavior, yellow to green for FTXT, scarlet red to turquoise green with different intermediate colors for PEXE. The band gaps of the polymers were found to be 2.23 eV and 1.74 eV for PTXT and PEXE, respectively. PTXT was also prepared via chemical polymerization and the obtained polymer was found to display blue light emission in chloroform with a relatively high quantum yield (Phi(f) = 0.59 in cyclohexane) despite having bluish-green light emission in the solid state. Both PTXT and PEXE are thermally stable with decomposition temperatures above 300 degrees C. (C)12 Elsevier Ltd. All rights reserved.