2,6-difluoro-N-(2-methoxyphenyl)aniline

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-difluoro-N-(2-methoxyphenyl)aniline
• 化学式: C₁₃H₁₁F₂NO
• 分子量: 235.233
• InChiKey: BKFMGIKHEMVVDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-difluoro-N-(2-methoxyphenyl)aniline 在 18-冠醚-6 、 三溴化硼 、 铜 、 potassium carbonate 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Hole-Transporting Materials with a Two-Dimensionally Expanded π-System around an Azulene Core for Efficient Perovskite Solar Cells

  摘要：

  Two-dimensionally expanded pi-systems, consisting of partially oxygen-bridged triarylamine skeletons that are connected to an azulene (1-3) or biphenyl core (4), were synthesized and characterized. When tetra-substituted azulene 1 was used as a hole-transporting material (HTM) in perovskite solar cells, the observed performance (power conversion efficiency = 16.5%) was found to be superior to that of the current HTM standard Spiro-OMeTAD. A comparison of the hole mobility, the ability to control the HOMO and LUMO levels, and the hole-collection efficiency at the perovskite/HTM interface in 1 with reference compounds (2-4 and Spiro-OMeTAD) led to the elucidation of key factors required for HTMs to act efficiently in perovskite solar cells.

  DOI：

  10.1021/jacs.5b11008
• 作为产物：
  描述：

  2-碘苯甲醚 、 2,6-二氟苯胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三叔丁基膦 作用下， 以 甲苯 为溶剂， 生成 2,6-difluoro-N-(2-methoxyphenyl)aniline
  参考文献：
  名称：

  氧桥二苯基萘胺作为全色圆偏振发光材料的支架

  摘要：

  设计并合成了螺旋形的氧桥联二苯基萘胺，将其作为圆偏振发光（CPL）材料的关键支架。在该骨架的萘基部分引入吸电子基团，例如甲酰基和2，2-二氰基乙烯基取代基，可有效降低LUMO能级，从而可调节带隙。制备的模型化合物在CH 2 Cl 2溶液和固态中均表现出强烈的CPL信号，其不对称因子（g值）为10 –3。这些衍生物的发光颜色既受取代基的影响，也受溶剂效应的影响，覆盖从蓝色到深红色的整个可见区域。

  DOI：

  10.1021/acs.joc.7b00511

文献信息

• COMPOUNDS FOR ELECTRONIC DEVICES
  申请人：Merck Patent GmbH

  公开号：US20200199154A1

  公开（公告）日：2020-06-25

  The present application relates to bridged triarylamines conforming to a defined formula. These compounds are suitable for use in electronic devices. The present application further relates to processes for preparing the compounds, and to electronic devices comprising the compounds.

  本申请涉及符合特定公式的桥接三芳胺。这些化合物适用于电子设备。本申请还涉及制备这些化合物的方法，以及包含这些化合物的电子设备。
• Oxygen-Bridged Diphenylnaphthylamine as a Scaffold for Full-Color Circularly Polarized Luminescent Materials
  作者：Hidetaka Nishimura、Kazuo Tanaka、Yasuhiro Morisaki、Yoshiki Chujo、Atsushi Wakamiya、Yasujiro Murata

  DOI：10.1021/acs.joc.7b00511

  日期：2017.5.19

  circularly polarized luminescent (CPL) materials. The introduction of electron-withdrawing groups, such as formyl and 2,2-dicyanovinyl substituents at the naphthyl moiety in this skeleton effectively decreases the LUMO level and thus allows a tuning of the band gap. The prepared model compounds exhibit intense CPL signals with a dissymmetry factor (g value) of 10–3 both in CH2Cl2 solutions and in the

  设计并合成了螺旋形的氧桥联二苯基萘胺，将其作为圆偏振发光（CPL）材料的关键支架。在该骨架的萘基部分引入吸电子基团，例如甲酰基和2，2-二氰基乙烯基取代基，可有效降低LUMO能级，从而可调节带隙。制备的模型化合物在CH 2 Cl 2溶液和固态中均表现出强烈的CPL信号，其不对称因子（g值）为10 –3。这些衍生物的发光颜色既受取代基的影响，也受溶剂效应的影响，覆盖从蓝色到深红色的整个可见区域。
• NOVEL COMPOUND, CHARGE TRANSPORT MATERIAL, AND ORGANIC DEVICE
  申请人：Wakamiya Atsushi

  公开号：US20140058099A1

  公开（公告）日：2014-02-27

  The compounds represented fey the following general formula is is thermally stable and has excellent characteristics as a charge transport material [Ar 1 represents a single bond, a benzene ring, etc.; X 1 represents a linking group that links via an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom or a silicon atom; either one of L 1 and L 2 , and L 3 and L 4 bond to each other to represent a linking group that links via an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom or a silicon atom; the other of L 1 and L 2 , and L 3 and L 4 represent a hydrogen atom or a substituent; Y 1 represents a linking group that links via a nitrogen atom, a boron atom or a phosphorus atom; R 1 , R 2 , R 5 to R 7 and R 10 to R 12 represent a hydrogen atom or a substituent; and n1 indicates an integer of 2 or more.].
• Influence of Alkoxy Chain Length on the Properties of Two‐Dimensionally Expanded Azulene‐Core‐Based Hole‐Transporting Materials for Efficient Perovskite Solar Cells
  作者：Minh Anh Truong、Jaehyun Lee、Tomoya Nakamura、Ji‐Youn Seo、Mina Jung、Masashi Ozaki、Ai Shimazaki、Nobutaka Shioya、Takeshi Hasegawa、Yasujiro Murata、Shaik Mohammed Zakeeruddin、Michael Grätzel、Richard Murdey、Atsushi Wakamiya

  DOI：10.1002/chem.201806317

  日期：2019.5.10

  of two‐dimensionally expanded azulene‐core‐based π systems have been synthesized with different alkyl chain lengths in the alkoxy moieties connected to the partially oxygen‐bridged triarylamine skeletons. The thermal, photophysical, and electronic properties of each compound were evaluated to determine the influence of the alkyl chain length on their effectiveness as hole‐transporting materials (HTMs)

  已经合成了一系列二维扩展的基于z烯核的π系统，这些烷基系统在与部分氧桥连的三芳基胺骨架连接的烷氧基部分具有不同的烷基链长。评估了每种化合物的热，光物理和电子性质，以确定烷基链长度对其在钙钛矿太阳能电池（PSC）中作为空穴传输材料（HTM）的有效性的影响。所有合成的分子均显示出令人鼓舞的材料特性，包括高溶解度，平坦和无定形膜的形成以及能级与钙钛矿的最佳对准。特别是甲基和n的衍生物侧链中的丁基丁基分别保持高达233和159°C的非晶态稳定性。这样的短烷氧基链也导致改善的电子器件性能。用具有正丁基侧链的HTM制成的PSC装置表现出最佳性能，功率转换效率为18.9％，与基于spiro-OMeTAD的PSC（spiro-OMeTAD = 2,2'，7， 7'-四[[ N，N-双（对-甲氧基苯基）氨基] -9,9'-螺二芴）。
• Hole-Transporting Materials with a Two-Dimensionally Expanded π-System around an Azulene Core for Efficient Perovskite Solar Cells
  作者：Hidetaka Nishimura、Naoki Ishida、Ai Shimazaki、Atsushi Wakamiya、Akinori Saeki、Lawrence T. Scott、Yasujiro Murata

  DOI：10.1021/jacs.5b11008

  日期：2015.12.23

  Two-dimensionally expanded pi-systems, consisting of partially oxygen-bridged triarylamine skeletons that are connected to an azulene (1-3) or biphenyl core (4), were synthesized and characterized. When tetra-substituted azulene 1 was used as a hole-transporting material (HTM) in perovskite solar cells, the observed performance (power conversion efficiency = 16.5%) was found to be superior to that of the current HTM standard Spiro-OMeTAD. A comparison of the hole mobility, the ability to control the HOMO and LUMO levels, and the hole-collection efficiency at the perovskite/HTM interface in 1 with reference compounds (2-4 and Spiro-OMeTAD) led to the elucidation of key factors required for HTMs to act efficiently in perovskite solar cells.