1,3-dibromo-6,7-bis(2-ethylhexyl)naphtho[2,3-c]thiophene-4,9-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-dibromo-6,7-bis(2-ethylhexyl)naphtho[2,3-c]thiophene-4,9-dione
• 英文别名: 1,3-dibromo-6,7-bis(2-ethylhexyl)naphtha[2,3-c]thiophene-4,9-dione；1,3-Dibromo-6,7-bis(2-ethylhexyl)benzo[f][2]benzothiole-4,9-dione
• 化学式: C₂₈H₃₆Br₂O₂S
• 分子量: 596.467
• InChiKey: PPFWXAYZTBLNFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-6,7-bis(2-ethylhexyl)naphtho[2,3-c]thiophene-4,9-dione 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.0h， 生成 1,3-bis(5-bromothiophen-2-yl)-6,7-bis(2-ethylhexyl)naphtho[2,3-c]thiophene-4,9-dione
  参考文献：
  名称：

  Enhanced photovoltaic effect from naphtho[2,3-c]thiophene-4,9-dione-based polymers through alkyl side chain induced backbone distortion

  摘要：

  合成了两种具有不同侧链取代位置的共轭聚合物，以研究它们的光伏性能。

  DOI：

  10.1039/d0ta02859b
• 作为产物：
  描述：

  邻二氯苯 在 草酰氯 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.34h， 生成 1,3-dibromo-6,7-bis(2-ethylhexyl)naphtho[2,3-c]thiophene-4,9-dione
  参考文献：
  名称：

  Enhanced photovoltaic effect from naphtho[2,3-c]thiophene-4,9-dione-based polymers through alkyl side chain induced backbone distortion

  摘要：

  合成了两种具有不同侧链取代位置的共轭聚合物，以研究它们的光伏性能。

  DOI：

  10.1039/d0ta02859b

文献信息

• ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS
  申请人：Brown Christopher T.

  公开号：US20110204341A1

  公开（公告）日：2011-08-25

  Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.

  可以用于有机电子器件和光伏电池的p型材料的高分子。化合物，单体，二聚体，三聚体和聚合物包括：可以实现良好的光伏效率和寿命。R基团可以提供可溶性，环境稳定性和光谱和/或电子性质的微调。可以制备不同的高分子微结构，以鼓励多重带隙和广泛而强烈的吸收。羰基可以与相邻的噻吩环相互作用，提供具有刚性的骨架，诱导平面性，并减少和/或消除分子内链扭曲缺陷。包含苯并噻吩和/或苯并噻二唑结构的高分子可以显示出特别高的性能。
• [EN] ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS<br/>[FR] POLYMÈRES ET DISPOSITIFS ORGANIQUES ÉLECTRIQUES, COMPRENANT DES CELLULES PHOTOVOLTAÏQUES ET DES POLYMÈRES À BASE DE DICÉTONE
  申请人：PLEXTRONICS INC

  公开号：WO2011028827A3

  公开（公告）日：2011-05-26
• Enhanced Photovoltaic Performance of Amorphous Copolymers Based on Dithienosilole and Dioxocycloalkene-annelated Thiophene
  作者：Jianming Huang、Yutaka Ie、Makoto Karakawa、Masahiko Saito、Itaru Osaka、Yoshio Aso

  DOI：10.1021/cm503117j

  日期：2014.12.23

  Organic photovoltaics (OPVs) have attracted considerable attention due to their potential for generating renewable energy. The power conversion efficiency (PCE) of the OPVs largely depends on the organic semiconducting materials. Thus, the elucidation of structureproperty OPV performance relationships is important for the rational improvement of OPVs. Here, low-bandgap copolymers comprising dithieno[3,2-b:2',3'-d]silole as a donor unit and dialkyl-substituted naphtho[2,3-c]thiophene-4,9-dione as an acceptor unit were synthesized to investigate the influence of the polymer molecular weight and the alkyl chain length in the acceptor unit on the polymer properties and photovoltaic performance. All the prepared copolymers are amorphous in the solid state. Both the increase of polymer molecular weight and variation of the alkyl side chains in the acceptor unit subtly affected molecular properties. However, these structural modifications showed significant impact on the photovoltaic performance in bulk heterojunction (BHJ) solar cells based on copolymer/[6,6]-phenyl-C-71-butyric acid methyl ester (PC71BM), with PCEs that range between 2.35 and 5.21%. Furthermore, the optimization of thin-film fabrication by use of a ternary solvent system led to the appearance of improved morphology accompanied by subtly ordered states of the copolymer in the BHJ films and, hence, improved carrier mobility and charge-separation efficiency. Consequently, the BHJ solar cell can achieve a PCE of 7.85%, which is the highest performance among the amorphous copolymers in the conventional device structure. This result highlights the importance of fine-tuning both the molecular structure and device fabrication in the construction of high-performance organic photovoltaics based on amorphous copolymers and PC71BM.
• US8968885B2
  申请人：——

  公开号：US8968885B2

  公开（公告）日：2015-03-03
• Enhanced photovoltaic effect from naphtho[2,3-<i>c</i>]thiophene-4,9-dione-based polymers through alkyl side chain induced backbone distortion
  作者：Xiaoman Bi、Tao Zhang、Cunbin An、Pengqing Bi、Kangqiao Ma、Sunsun Li、Kaihu Xian、Qianglong Lv、Shaoqing Zhang、Huifeng Yao、Bowei Xu、Jianqi Zhang、Shaokui Cao、Jianhui Hou

  DOI：10.1039/d0ta02859b

  日期：——

  Two conjugated polymers with different side chain substituted positions were synthesized to study their photovoltaic performances.

  合成了两种具有不同侧链取代位置的共轭聚合物，以研究它们的光伏性能。