4,9-二溴-2,7-双（2-己基癸基）苯并[lmn][3,8]菲咯啉-1,3,6,8（2H，7H）-四酮 | 1459168-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4,9-二溴-2,7-双（2-己基癸基）苯并[lmn][3,8]菲咯啉-1,3,6,8（2H，7H）-四酮
• 英文名称: 4,9-dibromo-2,7-bis(2-hexyldecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone
• 英文别名: 4,9-dibromo-2,7-bis(2-hexyldecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone；2,9-dibromo-6,13-bis(2-hexyldecyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone
• CAS: 1459168-68-3
• 化学式: C₄₆H₆₈Br₂N₂O₄
• 分子量: 872.865
• InChiKey: MBCCXMJGNFCYKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  54
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  4,9-二溴-2,7-双（2-己基癸基）苯并[lmn][3,8]菲咯啉-1,3,6,8（2H，7H）-四酮 在 三甲基乙酸钾 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 30.0h， 以62%的产率得到2-hydroxy-6-bromonaphthalene-1,4,5,8-tetracarboxylic-N,N′-bis(2-hexyldecyl)diimide
  参考文献：
  名称：

  C–H Arylation of Unsubstituted Furan and Thiophene with Acceptor Bromides: Access to Donor–Acceptor–Donor-Type Building Blocks for Organic Electronics

  摘要：

  Pd-catalyzed direct arylation (DA) reaction conditions have been established for unsubstituted furan (Fu) and thiophene (Th) with three popular acceptor building blocks to be used in materials for organic electronics, namely 4,7-dibromo-2,1,3-benzothiadiazole (BTBr2), N,N'-dialkylated 2,6-dibromonaphthalene-1,4,5,8-bis(dicarboximide) (NDIBr2), and 1,4-dibromotetrafluorobenzene (F4Br2). Reactions with BTBr2, F4Br2, and NDIBr2 require different solvents to obtain high yields. The use of dimethylacetamide (DMAc) is essential for the successful coupling of BTBr2 and F4Br2, but detrimental for NDIBr2, as the electron-deficient NDI core is prone to nucleophilic core substitution in DMAc as solvent but not in toluene. NDIFu(2) is much more planar compared to NDITh2, resulting in an enhanced charge-transfer character, which makes it an interesting building block for conjugated systems designed for organic electronics. This study highlights direct arylation as a simple and inexpensive method to construct a series of important donor-acceptor-donor building blocks to be further used for the preparation of a variety of conjugated materials.

  DOI：

  10.1021/jo502432e

文献信息

• Efficiency enhancement of organic solar cell by small molecule electrolyte based on naphthalene diimide as an electron transport layer
  作者：Rahmatia Fitri Binti Nasrun、Dong Hwan Son、Sabrina Aufar Salma、Joo Hyun Kim

  DOI：10.1080/15421406.2022.2046914

  日期：2022.7.24

  Abstract As an electron transport layer (ETL) for organic solar cells (OSCs), a naphthalene diimide (NDI)-based alcohol-soluble small molecule electrolyte (FN-NDI-Br) was designed and synthesized. The small molecule electrolyte was synthesized from the quaternization of the amino-terminal group in the alkyl chain. A bulk heterojunction (BHJ)-based inverted OSCs with the ITO/ZnO/ETL/PTB7-Th:PC71BM/MoO3/Ag

  摘要 作为有机太阳能电池（OSCs）的电子传输层（ETL），设计并合成了萘二亚胺（NDI）基醇溶性小分子电解质（FN-NDI-Br）。小分子电解质是由烷基链中氨基末端基团的季铵化合成的。制造了具有 ITO/ZnO/ETL/PTB7-Th:PC 71 BM/MoO 3 /Ag 结构的基于体异质结 (BHJ) 的倒置 OSC 。通过插入小分子电解质作为中间层来提高功率转换效率（PCE）。PTB7-Th和PC 71设备的设备性能BM 共混物作为光活性层和 FN-NDI 与乙酸添加剂作为 ETL 在具有原始 ZnO 的器件上从 8.53% 提高到 8.78%。与具有 FN-NDI 中间层的器件相比，通过修改侧链功能，器件的性能提高了 9.16%。
• Synthesis and characterization of small molecular electrolyte as an interlayer and its application in organic solar cells
  作者：Dong Hwan Son、Rahmatia Fitri Binti Nasrun、Young-Seok Shon、Joon-Seo Park、Joo Hyun Kim

  DOI：10.1080/15421406.2024.2330160

  日期：2024.4.12

  A small molecule electrolyte (SME) based on the iodide ion (FN-NDI-I) was synthesized for organic solar cells as interlayers based on fullerene and non-fullerene systems. The utilization of ITO/ZnO...

  合成了基于碘离子（FN-NDI-I）的小分子电解质（SME），用于有机太阳能电池作为基于富勒烯和非富勒烯系统的中间层。 ITO/ZnO的利用...