5,10-Dibromo-[2]benzofuro[5,4-e][2]benzofuran-1,3,6,8-tetrone | 1446011-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 5,10-Dibromo-[2]benzofuro[5,4-e][2]benzofuran-1,3,6,8-tetrone
• CAS: 1446011-21-7
• 化学式: C₁₄H₂Br₂O₆
• 分子量: 425.974
• InChiKey: CLWIMNDNMGOFNR-UHFFFAOYSA-N

物化性质

• 沸点：
  682.5±55.0 °C(Predicted)
• 密度：
  2.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  辛胺 、 5,10-Dibromo-[2]benzofuro[5,4-e][2]benzofuran-1,3,6,8-tetrone 在 溶剂黄146 作用下， 反应 3.0h， 以56%的产率得到
  参考文献：
  名称：

  1,2,5,6-Naphthalenediimide Based Donor–Acceptor Copolymers Designed from Isomer Chemistry for Organic Semiconducting Materials

  摘要：

  Two new donor-acceptor (D-A) copolymers based on 1,2,5,6-naphthalenediimides (iso-NDI) and thiophene units, isoP(NDI2OD-TT) and iso-P(NDI2OD-TT), were designed from isomer chemistry and compared with the reported isomeric copolymers P(NDI2OD-T2) and P(NDI2DT-TT) to investigate the influence of isomeric structure on their optoelectronic properties. DFT calculations reveal that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) have higher HOMO and LUMO energies and better backbone planarity relative to their isomeric polymers. IsoP(NDI2OD-T2) and iso-P(NDI2OD-TT) were synthesized by the Stille coupling polymerization and characterized by elemental analysis, H-1 NMR, GPC, UV-vis absorption, cyclic voltammetry, TGA, DSC, and organic thin film transistors (OTFTs). It was found that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) had higher LUMO energies and broader band gaps than their isomeric ones and showed hole-dominated charge transport behavior, which is quite different from the electron-dominated charge transport feature of P(NDI2OD-T2) and P(NDI2DT-TT). In spite of the amorphous-like thin-film features, iso-P(NDI2OD-T2) exhibited high hole mobility of up to 0.3 cm(2) V-1 s(-1), and isoP(NDI2OD-TT) showed ambipolar property with hole and electron mobility of up to 0.02 and 4 x 10(-3) cm(2) s(-1), respectively.

  DOI：

  10.1021/ma4013994
• 作为产物：
  描述：

  1,5-二溴-2,6-二甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 sodium dichromate dihydrate 、 硫酸 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 5,10-Dibromo-[2]benzofuro[5,4-e][2]benzofuran-1,3,6,8-tetrone
  参考文献：
  名称：

  1,2,5,6-Naphthalenediimide Based Donor–Acceptor Copolymers Designed from Isomer Chemistry for Organic Semiconducting Materials

  摘要：

  Two new donor-acceptor (D-A) copolymers based on 1,2,5,6-naphthalenediimides (iso-NDI) and thiophene units, isoP(NDI2OD-TT) and iso-P(NDI2OD-TT), were designed from isomer chemistry and compared with the reported isomeric copolymers P(NDI2OD-T2) and P(NDI2DT-TT) to investigate the influence of isomeric structure on their optoelectronic properties. DFT calculations reveal that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) have higher HOMO and LUMO energies and better backbone planarity relative to their isomeric polymers. IsoP(NDI2OD-T2) and iso-P(NDI2OD-TT) were synthesized by the Stille coupling polymerization and characterized by elemental analysis, H-1 NMR, GPC, UV-vis absorption, cyclic voltammetry, TGA, DSC, and organic thin film transistors (OTFTs). It was found that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) had higher LUMO energies and broader band gaps than their isomeric ones and showed hole-dominated charge transport behavior, which is quite different from the electron-dominated charge transport feature of P(NDI2OD-T2) and P(NDI2DT-TT). In spite of the amorphous-like thin-film features, iso-P(NDI2OD-T2) exhibited high hole mobility of up to 0.3 cm(2) V-1 s(-1), and isoP(NDI2OD-TT) showed ambipolar property with hole and electron mobility of up to 0.02 and 4 x 10(-3) cm(2) s(-1), respectively.

  DOI：

  10.1021/ma4013994

文献信息

• Tuning the frontier molecular orbital energy levels of<i>n</i>-type conjugated copolymers by using angular-shaped naphthalene tetracarboxylic diimides, and their use in all-polymer solar cells with high open-circuit voltages
  作者：Shan-Ci Chen、Qingdong Zheng、Qikai Zhang、Dongdong Cai、Jinyun Wang、Zhigang Yin、Changquan Tang

  DOI：10.1002/pola.26580

  日期：2013.5.1

  open‐circuit voltage (Voc) up to 0.94 V due to their relative high‐lying lowest unoccupied molecular orbital energy levels. The high Voc of 0.94 V is higher than that of solar cells based on linear‐shaped NDI‐containing polymers (<0.6 V). The results indicate that the angular‐shaped NDI is a promising building block for constructing nonfullerene polymer acceptors for solar cells with high open‐circuit

  设计并合成了角形萘四甲酸二酰亚胺（NDI），作为n型共轭聚合物的新构造单元以调节其能级。通过Stille偶联反应获得了三种以该角形NDI为受体部分的n型共聚物，其数均分子量为18.7–73.0 kDa。由这些聚合物与聚（3-己基噻吩）的混合物制成的全聚合物本体异质结太阳能电池的功率转换效率高达0.32％，并且由于其相对较高的特性而具有高达0.94 V的开路电压（V oc） -最低的未占用分子轨道能级。高V oc0.94 V的电压比基于线形含NDI的聚合物的太阳能电池（<0.6 V）高。结果表明，角形NDI是构建具有高开路电压的太阳能电池非富勒烯聚合物受体的有前途的构建基块。©2013 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年