2,6-dibromo-3,5-diphenyldithieno[3,2-b;2',3'-d]thiophene-S,Sdioxide | 1487464-98-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2,6-dibromo-3,5-diphenyldithieno[3,2-b;2',3'-d]thiophene-S,Sdioxide
• 英文别名: 4,10-Dibromo-5,9-diphenyl-3,7lambda6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide；4,10-dibromo-5,9-diphenyl-3,7λ6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide
• CAS: 1487464-98-1
• 化学式: C₂₀H₁₀Br₂O₂S₃
• 分子量: 538.304
• InChiKey: OZGANKQKXJDCKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-3,5-diphenyldithieno[3,2-b;2',3'-d]thiophene-S,Sdioxide 、 噻吩-2-硼酸频哪醇酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 生成
  参考文献：
  名称：

  Fluorene–Dithienothiophene-S,S-dioxide Copolymers. Fine-Tuning for OLED Applications

  摘要：

  Three groups of fluorene-dithieno[3,2-b;2',3'-d]-thiophene-S,S-dioxides (DTT-S,S-dioxide) copolymers, each having four different ratios of DTT-S,S-dioxide (5, 15, 25, and 50%) were successfully synthesized through Suzuki coupling method. While the first group copolymers PI had direct connection of fluorene to the peripheral thiophenes of DTT-S,S-dioxide, second group copolymers P2 had a thiophene extension between fluorene and DTT-S,S-dioxide, and in the third group, copolymers P3, fluorene had a connection with DTT-S,S-dioxide through the phenyl moiety of DTT. Absorbance and emission measurements of first two groups P1 and P2 displayed a regular bathochromic shift with increasing content of DTT-S,S-dioxide, which was more clearly observed in their solid state fluorescence measurements. Introduction of thiophene to the peripherals of the DTT-S,S-dioxide in copolymers P2 caused even further bathochromic shift in absorbances and emissions. As the absorbance and emission of PI went up to 447 and 558 nm in solution, respectively, P2 had them at 472 and 592 nm, respectively. In solid state, emissions of 131 and P2 even went further up to 585 and 646 nm, respectively. The bathochromic trend of 131 and P2 became opposite with absorbance and solid state emission of P3, which had a hypsochromic shift with increasing content of DTT-S,S-dioxide. Solid state emission of P3, particularly the copolymers having 5, 15 and 50% DTT-S,S-dioxide, covered a wide region between 400 and 675 nm. A spread of colors from light blue (border of white) to red through green and yellow was obtained with the OLED applications of the copolymers. Their optical and electronic band gaps varied between 2.17 and 2.99 eV and between 2.68 and 3.57 eV, respectively. While the highest quantum yield was obtained with P2 (5%) as 0.66, the lowest was observed with P2 (50%) as 0.03. Almost all of the polymers displayed good thermal stabilities. No weight loss was observed with the copolymers P2 (5-15%) and P3 up to 400 degrees C.

  DOI：

  10.1021/ma4016592
• 作为产物：
  描述：

  2,6-dibromo-3,5-diphenyldithieno[3,2-b;2',3'-d]thiophene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2,6-dibromo-3,5-diphenyldithieno[3,2-b;2',3'-d]thiophene-S,Sdioxide
  参考文献：
  名称：

  Fluorene–Dithienothiophene-S,S-dioxide Copolymers. Fine-Tuning for OLED Applications

  摘要：

  Three groups of fluorene-dithieno[3,2-b;2',3'-d]-thiophene-S,S-dioxides (DTT-S,S-dioxide) copolymers, each having four different ratios of DTT-S,S-dioxide (5, 15, 25, and 50%) were successfully synthesized through Suzuki coupling method. While the first group copolymers PI had direct connection of fluorene to the peripheral thiophenes of DTT-S,S-dioxide, second group copolymers P2 had a thiophene extension between fluorene and DTT-S,S-dioxide, and in the third group, copolymers P3, fluorene had a connection with DTT-S,S-dioxide through the phenyl moiety of DTT. Absorbance and emission measurements of first two groups P1 and P2 displayed a regular bathochromic shift with increasing content of DTT-S,S-dioxide, which was more clearly observed in their solid state fluorescence measurements. Introduction of thiophene to the peripherals of the DTT-S,S-dioxide in copolymers P2 caused even further bathochromic shift in absorbances and emissions. As the absorbance and emission of PI went up to 447 and 558 nm in solution, respectively, P2 had them at 472 and 592 nm, respectively. In solid state, emissions of 131 and P2 even went further up to 585 and 646 nm, respectively. The bathochromic trend of 131 and P2 became opposite with absorbance and solid state emission of P3, which had a hypsochromic shift with increasing content of DTT-S,S-dioxide. Solid state emission of P3, particularly the copolymers having 5, 15 and 50% DTT-S,S-dioxide, covered a wide region between 400 and 675 nm. A spread of colors from light blue (border of white) to red through green and yellow was obtained with the OLED applications of the copolymers. Their optical and electronic band gaps varied between 2.17 and 2.99 eV and between 2.68 and 3.57 eV, respectively. While the highest quantum yield was obtained with P2 (5%) as 0.66, the lowest was observed with P2 (50%) as 0.03. Almost all of the polymers displayed good thermal stabilities. No weight loss was observed with the copolymers P2 (5-15%) and P3 up to 400 degrees C.

  DOI：

  10.1021/ma4016592

文献信息

• Fluorene–Dithienothiophene-<i>S,S</i>-dioxide Copolymers. Fine-Tuning for OLED Applications
  作者：Ipek Osken、Ali Senol Gundogan、Emine Tekin、Mehmet S Eroglu、Turan Ozturk

  DOI：10.1021/ma4016592

  日期：2013.12.10

  Three groups of fluorene-dithieno[3,2-b;2',3'-d]-thiophene-S,S-dioxides (DTT-S,S-dioxide) copolymers, each having four different ratios of DTT-S,S-dioxide (5, 15, 25, and 50%) were successfully synthesized through Suzuki coupling method. While the first group copolymers PI had direct connection of fluorene to the peripheral thiophenes of DTT-S,S-dioxide, second group copolymers P2 had a thiophene extension between fluorene and DTT-S,S-dioxide, and in the third group, copolymers P3, fluorene had a connection with DTT-S,S-dioxide through the phenyl moiety of DTT. Absorbance and emission measurements of first two groups P1 and P2 displayed a regular bathochromic shift with increasing content of DTT-S,S-dioxide, which was more clearly observed in their solid state fluorescence measurements. Introduction of thiophene to the peripherals of the DTT-S,S-dioxide in copolymers P2 caused even further bathochromic shift in absorbances and emissions. As the absorbance and emission of PI went up to 447 and 558 nm in solution, respectively, P2 had them at 472 and 592 nm, respectively. In solid state, emissions of 131 and P2 even went further up to 585 and 646 nm, respectively. The bathochromic trend of 131 and P2 became opposite with absorbance and solid state emission of P3, which had a hypsochromic shift with increasing content of DTT-S,S-dioxide. Solid state emission of P3, particularly the copolymers having 5, 15 and 50% DTT-S,S-dioxide, covered a wide region between 400 and 675 nm. A spread of colors from light blue (border of white) to red through green and yellow was obtained with the OLED applications of the copolymers. Their optical and electronic band gaps varied between 2.17 and 2.99 eV and between 2.68 and 3.57 eV, respectively. While the highest quantum yield was obtained with P2 (5%) as 0.66, the lowest was observed with P2 (50%) as 0.03. Almost all of the polymers displayed good thermal stabilities. No weight loss was observed with the copolymers P2 (5-15%) and P3 up to 400 degrees C.