2,6-dibromonaphthalene-1,5-dicarboxylic acid | 1438248-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dibromonaphthalene-1,5-dicarboxylic acid
• CAS: 1438248-16-8
• 化学式: C₁₂H₆Br₂O₄
• 分子量: 373.985
• InChiKey: JHXLKEDJJSRJGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dibromonaphthalene-1,5-dicarboxylic acid 在 四(三苯基膦)钯 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 dimethyl 2,6-di(thiophen-2-yl)naphthalene-1,5-dicarboxylate
  参考文献：
  名称：

  Ladder-Type Dithienonaphthalene-Based Donor–Acceptor Copolymers for Organic Solar Cells

  摘要：

  A novel ladder-type dithienonaphthalene (DTN) was designed and synthesized as an electron-rich unit for constructing donor-acceptor copolymers. Different acceptor moieties, including benzo[c][1,2,5]thiadiazole (BT), 5,6-bis(hexyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBT), and 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,SH)-dione (TDPP), were used as electron-deficient units for the target copolymers. These copolymers (PDTNBT, PDTNTBT, and PDTNTDPP) were obtained via the Stile coupling reaction and characterized by H-1 NMR spectroscopy, UV-vis absorption spectroscopy, cyclic voltammetry, and gel permeation chromatography (GPC). Owing to the four solubilizing alkyl chains on the DTN unit, all the three copolymers have good solubility in common solvents. Among these polymers, PDTNTBT exhibits the highest space-charge limit current (SCLC) hole mobility of 2.13 x 10(-5) cm(2) V-1 s(-1), which is beneficial for achieving high performance solar cells. Under the simulated AM 1.5G illumination condition (100 mW/cm(2)), solar cells based on PDTNTBT:PC71BM (1:3, w/w) exhibit a power conversion efficiency (PCE) of 4.8% with a current density of 10.3 mA cm(-2), an open-circuit voltage of 0.86 V, and a fill factor of 54%. With the same device fabrication method, PDTNTDPP:PC71BM (1:3, w/w) and PDTNBT:PC71BM (1:3, w/w) based devices exhibit efficiencies of 1.52% and 2.79%, respectively. Furthermore, inverted solar cells based on these copolymer blends are also fabricated. The inverted devices based on PDTNTDPP:PC71BM (1:2, w/w) and PDTNBT:PC71BM (1:2, w/w) exhibit PCEs of 1.60% and 2.89%, respectively, which are similar to their corresponding conventional devices. And the inverted devices based on PDTNTBT:PC71BM (1:2, w/w) show a higher PCE of 5.0%, and more importantly, they are quite stable as demonstrated by the 4.75% PCE after ambient storage for two months.

  DOI：

  10.1021/ma400696e
• 作为产物：
  描述：

  2,6-dibromonaphthalene-1,5-dicarbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以88%的产率得到2,6-dibromonaphthalene-1,5-dicarboxylic acid
  参考文献：
  名称：

  Ladder-Type Dithienonaphthalene-Based Donor–Acceptor Copolymers for Organic Solar Cells

  摘要：

  A novel ladder-type dithienonaphthalene (DTN) was designed and synthesized as an electron-rich unit for constructing donor-acceptor copolymers. Different acceptor moieties, including benzo[c][1,2,5]thiadiazole (BT), 5,6-bis(hexyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBT), and 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,SH)-dione (TDPP), were used as electron-deficient units for the target copolymers. These copolymers (PDTNBT, PDTNTBT, and PDTNTDPP) were obtained via the Stile coupling reaction and characterized by H-1 NMR spectroscopy, UV-vis absorption spectroscopy, cyclic voltammetry, and gel permeation chromatography (GPC). Owing to the four solubilizing alkyl chains on the DTN unit, all the three copolymers have good solubility in common solvents. Among these polymers, PDTNTBT exhibits the highest space-charge limit current (SCLC) hole mobility of 2.13 x 10(-5) cm(2) V-1 s(-1), which is beneficial for achieving high performance solar cells. Under the simulated AM 1.5G illumination condition (100 mW/cm(2)), solar cells based on PDTNTBT:PC71BM (1:3, w/w) exhibit a power conversion efficiency (PCE) of 4.8% with a current density of 10.3 mA cm(-2), an open-circuit voltage of 0.86 V, and a fill factor of 54%. With the same device fabrication method, PDTNTDPP:PC71BM (1:3, w/w) and PDTNBT:PC71BM (1:3, w/w) based devices exhibit efficiencies of 1.52% and 2.79%, respectively. Furthermore, inverted solar cells based on these copolymer blends are also fabricated. The inverted devices based on PDTNTDPP:PC71BM (1:2, w/w) and PDTNBT:PC71BM (1:2, w/w) exhibit PCEs of 1.60% and 2.89%, respectively, which are similar to their corresponding conventional devices. And the inverted devices based on PDTNTBT:PC71BM (1:2, w/w) show a higher PCE of 5.0%, and more importantly, they are quite stable as demonstrated by the 4.75% PCE after ambient storage for two months.

  DOI：

  10.1021/ma400696e

文献信息

• A hexacyclic ladder-type building block for high-performance D–A copolymers
  作者：Liu Qian、Jiamin Cao、Liming Ding

  DOI：10.1039/c5ta07942j

  日期：——

  Two D–A copolymers PThTITI and PSeTITI were developed by copolymerizing a novel ladder-type building block TITI with thiophene (Th) or selenophene (Se). PThTITI:PC₇₁BM and PSeTITI:PC₇₁BM solar cells gave PCEs of 5.53% and 6.17%, respectively.

  通过共聚合一种新型阶梯型建筑单元TITI和噻吩(Th)或硒吩(Se)，开发了两种D-A共聚物PThTITI和PSeTITI。PThTITI:PC71BM和PSeTITI:PC71BM太阳能电池的光电转换效率分别为5.53%和6.17%。