2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene] | 872514-82-4

• 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-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3',6'-di-n-octyloxyspiro[fluorene-9,9'-xanthene]
• 英文别名: 2-[3',6'-Dioctoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[3',6'-dioctoxy-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 872514-82-4
• 化学式: C₅₃H₇₀B₂O₇
• 分子量: 840.757
• InChiKey: ZOOSPQPCRKBPFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.23
• 重原子数：
  62
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,7-二溴-9-芴酮 在 盐酸 、 正丁基锂 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 21.0h， 生成 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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

• 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.