2,6-dibromo-1,5-dimethylnaphthalene | 111650-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dibromo-1,5-dimethylnaphthalene
• CAS: 111650-45-4
• 化学式: C₁₂H₁₀Br₂
• 分子量: 314.019
• InChiKey: WUQLGSSIGCZGAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-1,5-dimethylnaphthalene 在 sodium chlorite 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 草酰氯 、 水 、 二甲基亚砜 、 calcium carbonate 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 88.67h， 生成 dimethyl 2,6-dibromonaphthalene-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：

  1,5-二甲基萘 在 溴 、 铁粉 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以29%的产率得到2,6-dibromo-1,5-dimethylnaphthalene
  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

• NOVEL FUSED NAPHTHALENE CYCLOHETERO RING COMPOUNDS, AND METHODS AND USES THEREOF
  申请人：Corning Incorporated

  公开号：US20150045560A1

  公开（公告）日：2015-02-12

  Described herein are heterocyclic organic compounds of following formulae: More specifically, described herein are fused heterocyclic naphthalene compounds, polymers based on fused heterocyclic naphthalene compounds, methods for making these compounds, and uses thereof. The compounds described have improved polymerization and stability properties that allow for improved material processibility for use as organic semiconductors (OSCs).

  本文描述了以下式子的杂环有机化合物：更具体地，本文描述了融合的杂环萘化合物，基于融合的杂环萘化合物的聚合物，制备这些化合物的方法以及它们的用途。所描述的化合物具有改善的聚合和稳定性能，可用作有机半导体（OSC），从而提高材料的加工性能。
• Pozdnyakovich, S. A.; Shigalevskii, V. A.; Pozdnyakovich, Yu. V., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 145 - 150
  作者：Pozdnyakovich, S. A.、Shigalevskii, V. A.、Pozdnyakovich, Yu. V.

  DOI：——

  日期：——
• POZDNYAKOVICH S. A.; SHIGALEVSKIJ V. A.; POZDNYAKOVICH YU. V., ZH. ORGAN. XIMII, 23,(1987) N 1, 161-167
  作者：POZDNYAKOVICH S. A.、 SHIGALEVSKIJ V. A.、 POZDNYAKOVICH YU. V.

  DOI：——

  日期：——
• Synthesis of Polynaphthalenes and Their Use
  申请人：Doetz Florian

  公开号：US20070287821A1

  公开（公告）日：2007-12-13

  The present invention relates to a process for preparing polynaphthalene derivatives comprising repeating units of the general formula Ia and/or Ib where R 1 , R 2 , R 1′ , R 2′ are as defined in the description. The present invention further relates to polynaphthalene derivatives which can be prepared by the process of the invention, films comprising or consisting of at least one polynaphthalene derivative according to the invention, organic light-emitting diodes (OLEDs) comprising at least one polynaphthalene derivative according to the invention, a light-emitting layer comprising or consisting of at least one polynaphthalene derivative according to the invention, an OLED comprising the light-emitting layer of the invention, devices comprising an OLED according to the invention and the use of the polynaphthalene derivatives of the invention as emitter substances in OLEDs.
• Ladder-Type Dithienonaphthalene-Based Donor–Acceptor Copolymers for Organic Solar Cells
  作者：Yunlong Ma、Qingdong Zheng、Zhigang Yin、Dongdong Cai、Shan-Ci Chen、Changquan Tang

  DOI：10.1021/ma400696e

  日期：2013.6.25

  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.