3,6-dibromo-4,5-bis(hexyloxy)benzene-1,2-diamine | 1190978-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,6-dibromo-4,5-bis(hexyloxy)benzene-1,2-diamine
• CAS: 1190978-95-0
• 化学式: C₁₈H₃₀Br₂N₂O₂
• 分子量: 466.256
• InChiKey: FOZDGIOYZBGHFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  41.7-44.5 °C
• 沸点：
  488.8±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,6-dibromo-4,5-bis(hexyloxy)benzene-1,2-diamine 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 2-cyano-3-(5-(8-(5-(4-(diphenylamino)phenyl)furan-2-yl)-6,7-bis(hexyloxy)-2,3-dimethylquinoxalin-5-yl)fura-2-yl)acrylic acid
  参考文献：
  名称：

  New sensitizers bearing quinoxaline moieties as an auxiliary acceptor for dye-sensitized solar cells

  摘要：

  Two organic sensitizers (LI-40 and LI-41) containing 6,7-bis(hexyloxy)-2,3-dimethylquinoxaline unit and thiophene or furan as conjugated bridge were synthesized and utilized for dye-sensitized solar cells (DSSCs). The incorporation of quinoxaline unit brought about impressive changes in absorption spectra and energy levels, thus, enhanced the light-harvesting for photovoltaic conversion and facilitated the electron transfer, resulting in a great improvement in the electron distribution of the whole molecule. The solar cell based on LI-40 exhibited a broad incident photon-to-current conversion efficiency (IPCE) spectrum and high conversion efficiency (eta = 6.75%). While under the same measuring conditions, the reference sensitizer PSS, which had similar structure to LI-40 but without the quinoxaline unit in the conjugated bridge, only gave the eta value of 4.50%, indicating that the sensitizers are promising candidates to improve the performance of DSSCs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.03.015

文献信息

• High performance organic sensitizers based on 11,12-bis(hexyloxy) dibenzo[a,c]phenazine for dye-sensitized solar cells
  作者：Jie Shi、Junnian Chen、Zhaofei Chai、Heng Wang、Runli Tang、Ke Fan、Mei Wu、Hongwei Han、Jingui Qin、Tianyou Peng、Qianqian Li、Zhen Li

  DOI：10.1039/c2jm33833e

  日期：——

  Three new metal-free organic sensitizers containing 11,12-bis(hexyloxy) dibenzo[a,c]phenazine (BPz) units were synthesized and used for dye-sensitized solar cells (DSSCs). The broad absorption spectra indicate that the light harvesting abilities were enhanced by the introduction of the BPz unit in the π-conjugated space, which can also cause an anti-aggregation effect and the suppression of charge recombination. Among these sensitizers, LI-39 showed the best photovoltaic performance: a short-circuit photocurrent density (Jsc) of 14.40 mA cm−2, an open-circuit photovoltage (Voc) of 0.74 V, and a fill factor (ff) of 0.67, corresponding to an overall conversion efficiency of 7.18% under standard global AM 1.5 solar light conditions. The result shows that the organic sensitizers based on this bulky fused aromatic rings as well as the auxiliary acceptor are the promising candidates for improvement of the performance of DSSCs.

  我们合成了三种新的不含金属的有机敏化剂，其中含有11,12-双(己氧基)二苯并[a,c]菲嗪(BPz)单元，并将其用于染料敏化太阳能电池(DSSC)。宽吸收光谱表明，在π共轭空间引入BPz单元可以增强光捕获能力，同时还能产生抗聚集效应并抑制电荷复合。在这些敏化剂中，LI-39的光电性能最佳：短路光电流密度(Jsc)为14.40 mA cm−2，开路光电压(Voc)为0.74 V，填充因子(ff)为0.67，在标准全球AM 1.5太阳光条件下，总转换效率为7.18%。结果表明，基于这种大体积稠环芳烃的有机敏化剂以及辅助受体是提高DSSC性能的有前景的候选材料。