2,2'-(5,5'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) | 1310344-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,2'-(5,5'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: 2-[5-[9,9-Dioctyl-7-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]fluoren-2-yl]thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[5-[9,9-dioctyl-7-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]fluoren-2-yl]thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1310344-83-2
• 化学式: C₄₉H₆₈B₂O₄S₂
• 分子量: 806.831
• InChiKey: XSNDXWFOLUUMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.51
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9,9-二辛基芴-2,7-双(硼酸频哪醇酯) 在 四(三苯基膦)钯 、 正丁基锂 、 甲基三辛基氯化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 hexanes 、 甲苯 为溶剂， 反应 48.5h， 生成 2,2'-(5,5'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  参考文献：
  名称：

  Introduction of Perylene Units for Enhanced Interchain Interaction in Conjugated Polymers for Organic Photovoltaic Devices

  摘要：

  A series of semiconducting copolymers, poly[2,7-(9,9'-dioctylfluorene)-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PFDTBT), poly[2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)dithiophene-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PFD2TBT), and their ter-polymers containing perylene units were synthesized using Suzuki coupling polymerization. The perylene units were introduced to improve the charge-transport ability by enhancing the pi-pi interaction between polymer chains. The resulting polymers were characterized by H-1 NMR, elemental analysis, DSC, and TGA. The synthesized polymers were soluble in common organic solvents, and formed smooth and uniform spin-coated thin films. All of the polymers studied were found to exhibit good thermal stability, losing less than 5% of their weight upon heating to approximately 350 degrees C. Perylene- containing polymers showed higher field-effect mobilities than the corresponding PFDTBT or PFD2TBT polymers because of the enhanced pi-pi interaction between polymer chains upon the introduction of perylene units. Bulk heterojunction solar cells were fabricated with configuration of ITO/PEDOT:PSS/polymer:PC71BM/TiOx/Al. The devices using the perylene-containing polymers showed higher short-circuit currents, and fill factors than the corresponding PFDTBT or PFD2TBT devices. One of the fabricated devices using a perylene-containing copolymer showed a maximum power conversion efficiency of 3.16%, with a short circuit current density of 9.61 mA/cm(2), open circuit voltage of 0.81 V, and fill factor of 41%.

  DOI：

  10.1021/ma202712r

文献信息

• Introduction of Perylene Units for Enhanced Interchain Interaction in Conjugated Polymers for Organic Photovoltaic Devices
  作者：Ji-Hoon Kim、Hee Un Kim、Dongbo Mi、Sung-Ho Jin、Won Suk Shin、Sung Cheol Yoon、In-Nam Kang、Do-Hoon Hwang

  DOI：10.1021/ma202712r

  日期：2012.3.13

  A series of semiconducting copolymers, poly[2,7-(9,9'-dioctylfluorene)-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PFDTBT), poly[2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)dithiophene-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PFD2TBT), and their ter-polymers containing perylene units were synthesized using Suzuki coupling polymerization. The perylene units were introduced to improve the charge-transport ability by enhancing the pi-pi interaction between polymer chains. The resulting polymers were characterized by H-1 NMR, elemental analysis, DSC, and TGA. The synthesized polymers were soluble in common organic solvents, and formed smooth and uniform spin-coated thin films. All of the polymers studied were found to exhibit good thermal stability, losing less than 5% of their weight upon heating to approximately 350 degrees C. Perylene- containing polymers showed higher field-effect mobilities than the corresponding PFDTBT or PFD2TBT polymers because of the enhanced pi-pi interaction between polymer chains upon the introduction of perylene units. Bulk heterojunction solar cells were fabricated with configuration of ITO/PEDOT:PSS/polymer:PC71BM/TiOx/Al. The devices using the perylene-containing polymers showed higher short-circuit currents, and fill factors than the corresponding PFDTBT or PFD2TBT devices. One of the fabricated devices using a perylene-containing copolymer showed a maximum power conversion efficiency of 3.16%, with a short circuit current density of 9.61 mA/cm(2), open circuit voltage of 0.81 V, and fill factor of 41%.