2,9-diboronic ester-N,N'-di(2-octyldodecyl)quinacridone | 1400665-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,9-diboronic ester-N,N'-di(2-octyldodecyl)quinacridone
• 英文别名: 5,12-Bis(2-octyldodecyl)-2,9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolino[2,3-b]acridine-7,14-dione
• CAS: 1400665-71-5
• 化学式: C₇₂H₁₁₄B₂N₂O₆
• 分子量: 1125.33
• InChiKey: PHDKSJSBOMNCMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.02
• 重原子数：
  82
• 可旋转键数：
  38
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,9-dibromo-N,N'-di(2-octyldodecyl)quinacridone 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2,9-diboronic ester-N,N'-di(2-octyldodecyl)quinacridone
  参考文献：
  名称：

  Donor–acceptor copolymers containing quinacridone and benzothiadiazole for thin film transistors

  摘要：

  我们合成了两种供体-受体共聚物 PQB 和 PQBOC8，其中含有供体成分喹吖啶酮和受体成分苯并噻二唑。与 PQB 相比，在 PQBOC8 的苯并噻二唑上引入两条额外的烷氧基链不仅提高了溶解度和分子量，还改变了光电化学特性和聚合物链的构象。因此，它们表现出不同的薄膜微观结构和晶体管性能。事实上，PQBOC8呈现出有序的层状结构，链与链之间的距离为21.5 Ã，ÏâÏ堆积距离为4.0 Ã，在环境条件下的空穴迁移率高达0.30 cm2 Vâ1 sâ1，而PQB则呈现出高度无序的薄膜微观结构，空穴迁移率为5.77 à 10â3 cm2 Vâ1 sâ1。

  DOI：

  10.1039/c3tc00550j

文献信息

• Conjugated Polymer Consisting of Quinacridone and Benzothiadiazole as Donor Materials for Organic Photovoltaics: Coplanar Property of Polymer Backbone
  作者：Ho-Jun Song、Doo-Hun Kim、Eui-Jin Lee、Soo-Won Heo、Jang-Yong Lee、Doo-Kyung Moon

  DOI：10.1021/ma301466m

  日期：2012.10.9

  Highly soluble poly[quinacridone-alt-benzothiadiazole] (PQCDTB) has been synthesized through the Suzuki coupling reaction by introducing planar quinacridone and highly absorbing benzothiadiazole. The PQCDTB dissolved in general organic solvents, and the M-n was 49.8 kg/mol. The optical band gap energy was 1.92 eV, which was similar to the band gap of benzothiadiazole. The HOMO and LUMO levels of PQCDTB were -5.24 eV and -3.32 eV, respectively. According to the XRD measurement, PQCDTB showed the formation of ordered lamellar structure as an out-of-plane peak (h00) by the alkyl side chain of quinacridone and conventional edge-on pi- stacking. This study also evaluated the OPV characteristics by fabricating a bulk-heterojunction-type polymer solar cell. When PQCDTB and PC71BM were fabricated in a 1:1 weight ratio, the open-circuit voltage (V-OC), short-circuit current (J(SC)), fill factor (FF), and power conversion efficiency (PCE) were 0.79 V, 5.6 mA cm(-2), 55.8% and 2.5%, respectively. In particular, PQCDTB exhibited higher FFs compared with poly[carbazole-alt-benzothiadiazole] (PCZDTB).