2,6-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole | 1443677-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,6-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole
• 英文别名: 7-(4-Octylphenyl)-4,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1443677-03-9
• 化学式: C₃₄H₄₇B₂NO₄S₂
• 分子量: 619.505
• InChiKey: PHBFLQVYHAOTMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  98.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 6.08h， 生成 2,6-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  Synthesis of N-[4-Octylphenyl]dithieno[3,2-b:2′,3′-d]pyrrole-based broad absorbing polymers and their photovoltaic applications

  摘要：

  Electron rich, fused N-aryl pyrrole based monomer namely 2,6-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole (N-aryl DTP) was synthesized and copolymerized with electron deficient 4,7-bis(5-bromo-3-octyl-2-thienyl)-2,1,3-benzothiadiazole (TBT) to afford alternating polymer PDTPTBT. The absorption band of PDTPTBT was found to cover the entire visible part of the solar spectrum (300 nm-750 nm) and the optical band gap was estimated to be 1.62 eV. In order to extent the absorption of PDTPTBT, another strong electron acceptor unit such as 2,1,3-benzothiadiazole or dimethyl-2H-benzimidazole was incorporated in polymer main chain by copolymerizing three different comonomers (N-aryl DTP, TBT and 4,7-dibromo-2,1,3-benzothiadiazole (B) or 4,7-dibromo-2,2-dimethyl-2H-benzimidazole (BI)) at 2:1:1 ratio to afford polymers PDTPTBTB and PDTPTBTBI, respectively. The absorption band of PDTPTBTB and PDTPTBTBI was found to be extended up to 1000 nm and 1200 nm, respectively, and the optical band gap was calculated to be 1.33 eV and 1.07 eV, respectively. The HOMO-LUMO energy levels of PDTPTBT, PDTPTBTB and PDTPTBTBI were found to be suitable for polymer solar cell (PSC) applications. The single layer PSCs fabricated with the configuration of ITO/PEDOT:PSS/PDTPTBT, PDTPTBTB or PDTPTBTBI:PC60BM(1:3 wt/wt)/LiF/Al showed maximum power conversion efficiency (PCE) of 2.04%, 1.01% and 0.70%, respectively. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.04.049