2,7-dibromo-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene] | 872514-81-3

• 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: 2,7-dibromo-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene]
• 英文别名: 2,7-dibromo-3',6'-bis(octyloxy)spiro[fluorene-9,9'-xanthene]；3',6'-bis(octyloxy)-2,7-dibromospiro[fluorene-9,9'-xanthene]；2,7-Dibromo-3',6'-dioctoxyspiro[fluorene-9,9'-xanthene]；2,7-dibromo-3',6'-dioctoxyspiro[fluorene-9,9'-xanthene]
• CAS: 872514-81-3
• 化学式: C₄₁H₄₆Br₂O₃
• 分子量: 746.622
• InChiKey: IKGMPWXREVAIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,7-dibromo-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene] 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Stable Organic Blue-Light-Emitting Devices Prepared from Poly[spiro(fluorene-9,9‘-xanthene)]

  摘要：

  A short, efficient synthetic route has been developed for the preparation of 2,7-dibromospiro-[fluorene-9,9'-(2',7'-di-n-octyloxyxanthene)], which was subsequently polymerized with the corresponding diborolane through Suzuki coupling to afford a fluorene-based homopolymer, PSFX, that contains a spiroxanthene group functionalized on the C-9 position of each fluorene repeat unit. Single-crystal X-ray diffraction analysis of the dibromo monomer revealed that the spiro-fused fluorene and xanthene moieties lie perpendicular to one another. As a consequence of the incorporation of the spiro pendant group, PSFX possesses a high glass transition temperature and good thermal stability while displaying its stable blue emission in the solid state. A light-emitting diode device prepared using PSFX as the emitting layer exhibits an efficient, stable blue emission; it has a turn-on voltage of 6 V and a maximum external quantum efficiency of 1.74% ph/el. Even when the brightness was increased up to 10(3) cd/m(2) (ca. 11 V), the CIE color coordinates of the resulting EL spectrum remained in the deep-blue region (0.15, 0.07) and the device's efficiency was 1.33% ph/el.

  DOI：

  10.1021/ma051798f
• 作为产物：
  描述：

  2,7-二溴-9-芴酮 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2,7-dibromo-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene]
  参考文献：
  名称：

  Stable Organic Blue-Light-Emitting Devices Prepared from Poly[spiro(fluorene-9,9‘-xanthene)]

  摘要：

  A short, efficient synthetic route has been developed for the preparation of 2,7-dibromospiro-[fluorene-9,9'-(2',7'-di-n-octyloxyxanthene)], which was subsequently polymerized with the corresponding diborolane through Suzuki coupling to afford a fluorene-based homopolymer, PSFX, that contains a spiroxanthene group functionalized on the C-9 position of each fluorene repeat unit. Single-crystal X-ray diffraction analysis of the dibromo monomer revealed that the spiro-fused fluorene and xanthene moieties lie perpendicular to one another. As a consequence of the incorporation of the spiro pendant group, PSFX possesses a high glass transition temperature and good thermal stability while displaying its stable blue emission in the solid state. A light-emitting diode device prepared using PSFX as the emitting layer exhibits an efficient, stable blue emission; it has a turn-on voltage of 6 V and a maximum external quantum efficiency of 1.74% ph/el. Even when the brightness was increased up to 10(3) cd/m(2) (ca. 11 V), the CIE color coordinates of the resulting EL spectrum remained in the deep-blue region (0.15, 0.07) and the device's efficiency was 1.33% ph/el.

  DOI：

  10.1021/ma051798f

文献信息

• Spiro-substitution effect of terfluorenes on amplified spontaneous emission and lasing behaviors
  作者：Zongyan Zuo、Changjin Ou、Yongjie Ding、He Zhang、Sixian Sun、Linghai Xie、Ruidong Xia、Wei Huang

  DOI：10.1039/c8tc00714d

  日期：——

  Spiro terfluorenes are shown to have improved ASE properties and the impressive lasing threshold of terfluorenes is demonstrated.

  螺环三芴烯显示出改善的ASE属性，并展示了三芴烯的令人印象深刻的激光阈值。
• 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.
• Stable Organic Blue-Light-Emitting Devices Prepared from Poly[spiro(fluorene-9,9‘-xanthene)]
  作者：Ya-Hsien Tseng、Ping-I Shih、Chen-Han Chien、Ajay Kumar Dixit、Ching-Fong Shu、Yi-Hung Liu、Gene-Hsiang Lee

  DOI：10.1021/ma051798f

  日期：2005.11.1

  A short, efficient synthetic route has been developed for the preparation of 2,7-dibromospiro-[fluorene-9,9'-(2',7'-di-n-octyloxyxanthene)], which was subsequently polymerized with the corresponding diborolane through Suzuki coupling to afford a fluorene-based homopolymer, PSFX, that contains a spiroxanthene group functionalized on the C-9 position of each fluorene repeat unit. Single-crystal X-ray diffraction analysis of the dibromo monomer revealed that the spiro-fused fluorene and xanthene moieties lie perpendicular to one another. As a consequence of the incorporation of the spiro pendant group, PSFX possesses a high glass transition temperature and good thermal stability while displaying its stable blue emission in the solid state. A light-emitting diode device prepared using PSFX as the emitting layer exhibits an efficient, stable blue emission; it has a turn-on voltage of 6 V and a maximum external quantum efficiency of 1.74% ph/el. Even when the brightness was increased up to 10(3) cd/m(2) (ca. 11 V), the CIE color coordinates of the resulting EL spectrum remained in the deep-blue region (0.15, 0.07) and the device's efficiency was 1.33% ph/el.