2,6-dibromo-3,7-bis(phenylethynyl)naphthalene | 1227744-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dibromo-3,7-bis(phenylethynyl)naphthalene
• 英文别名: 2,6-Dibromo-3,7-bis(2-phenylethynyl)naphthalene
• CAS: 1227744-11-7
• 化学式: C₂₆H₁₄Br₂
• 分子量: 486.205
• InChiKey: CLHUKIIHSJZCBP-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: hexane (110-54-3))
• 沸点：
  616.1±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-3,7-bis(phenylethynyl)naphthalene 在 sodiumsulfide nonahydrate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 以86%的产率得到2,7-diphenylnaphtho[2,3-b:6,7-b']dithiophene
  参考文献：
  名称：

  线性和角形萘二噻吩：选择性合成、性质和在有机场效应晶体管中的应用

  摘要：

  描述了一种直接的合成方法，该方法利用线性和角形萘二噻吩 (NDT) 作为有机半导体的新核心结构的潜力。新建立的合成程序包括两个重要步骤；一种是溴位点上的三氟甲磺酰氧基位点上的化学选择性 Sonogashira 偶联反应，能够选择性地在萘核上形成邻溴乙炔基苯亚结构，另一种是来自邻溴乙炔基苯亚结构的稠合噻吩环的简便闭环反应。结果，三种异构无损检测，萘并[2,3-b:6,7-b']二噻吩、萘并[2,3-b:7,6-b']二噻吩和萘并[2,1-b :6,5-b']二噻吩是选择性合成的。母体无损检测的电化学和光学测量表明，分子的形状在决定化合物的电子结构方面起着重要作用；与并四苯等电子的线形无损检测相比，与并四苯等电子的角形无损检测具有更低的氧化电位和更多的红移吸收带。相反，使用二辛基或二苯基衍生物的薄膜场效应晶体管（FET）的性能受分子对称性的影响很大；中心对称衍生物往往比轴对称衍生物（~0.06

  DOI：

  10.1021/ja110973m
• 作为产物：
  描述：

  2,6-萘二酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 铁粉 吡啶 、 tin 、 溴 、 溶剂黄146 、 二异丙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 164.5h， 生成 2,6-dibromo-3,7-bis(phenylethynyl)naphthalene
  参考文献：
  名称：

  Novel Compound, Method of Producing the Compound, Organic Semiconductor Material and Organic Semiconductor Device

  摘要：

  提供了一种具有良好场效率的新型化合物，一种生产该化合物的方法，含有该新型化合物的有机半导体材料以及有机半导体器件。该新型化合物由以下通用式（1）、（2）、（3）或（4）表示（其中Z代表硫原子或硒原子，R代表通常式中的氢原子、烷基或苯基），具有两个萘烯环与噻吩环和硒吩环分别结合的结构。这些化合物在分子中具有共轭系统，由于轨道之间的相互作用，通过每个分子中噻吩环或硒吩环中含有的硫原子或硒原子显示出强烈的分子间相互作用，从而具有良好的场效率。

  公开号：

  US20110224445A1

文献信息

• NOVEL COMPOUND, PROCESS FOR PRODUCING THE COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC SEMICONDUCTOR DEVICE
  申请人：Hiroshima University

  公开号：EP2368892A1

  公开（公告）日：2011-09-28

  There are provided a novel compound having a good field mobility, a method of producing of the compound, an organic semiconductor material containing the novel compound, and an organic semiconductor device. The novel compound which is represented by the following general formula (1), (2), (3) or (4) (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in general formulae) has a structure having two benzene rings of naphthalene bonded with a thiophene ring and a selenophene ring, respectively. These compounds have a conjugate system in molecules due to an interaction between π orbitals, and show a strong molecular interaction through a sulfur atom or a selenium atom contained in a thiophene ring or a selenophene ring in each molecule, thereby having a good field mobility.

  本文提供了一种具有良好场迁移率的新型化合物、一种生产该化合物的方法、一种含有该新型化合物的有机半导体材料以及一种有机半导体器件。由以下通式(1)、(2)、(3)或(4)表示的新型化合物（通式中 Z 代表硫原子或硒原子，R 代表氢原子、烷基或苯基）具有两个萘苯环分别与一个噻吩环和一个硒吩环键合的结构。由于 π 轨道之间的相互作用，这些化合物在分子中形成共轭体系，并通过每个分子中的噻吩环或 硒吩环所含的一个硫原子或一个硒原子显示出强烈的分子相互作用，从而具有良好的场迁移率。
• Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices
  作者：Masahiro Nakano、Hiroki Mori、Shoji Shinamura、Kazuo Takimiya

  DOI：10.1021/cm202853b

  日期：2012.1.10

  New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C-60 or C-70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm(2) V-1 s(-1) and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.
• DESCRIPTION NOVEL COMPUND, METHOD OF PRODUCING THE COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL AND ORGANIC SEMICONDUCTOR DEVICE
  申请人：Hiroshima University

  公开号：US20140051865A1

  公开（公告）日：2014-02-20

  There are provided a novel compound having a good field mobility, a method of producing of the compound, an organic semiconductor material containing the novel compound, and an organic semiconductor device. The novel compound which is represented by the following general formula (1), (2), (3) or (4) (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in general formulae) has a structure having two benzene rings of naphthalene bonded with a thiophene ring and a selenophene ring, respectively. These compounds have a conjugate system in molecules due to an interaction between π orbitals, and show a strong molecular interaction through a sulfur atom or a selenium atom contained in a thiophene ring or a selenophene ring in each molecule, thereby having a good field mobility.
• US8816100B2
  申请人：——

  公开号：US8816100B2

  公开（公告）日：2014-08-26
• Novel Compound, Method of Producing the Compound, Organic Semiconductor Material and Organic Semiconductor Device
  申请人：Takimiya Kazuo

  公开号：US20110224445A1

  公开（公告）日：2011-09-15

  There are provided a novel compound having a good field mobility, a method of producing of the compound, an organic semiconductor material containing the novel compound, and an organic semiconductor device. The novel compound which is represented by the following general formula (1), (2), (3) or (4) (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in general formulae) has a structure having two benzene rings of naphthalene bonded with a thiophene ring and a selenophene ring, respectively. These compounds have a conjugate system in molecules due to an interaction between it orbitals, and show a strong molecular interaction through a sulfur atom or a selenium atom contained in a thiophene ring or a selenophene ring in each molecule, thereby having a good field mobility.

  提供了一种具有良好场效率的新型化合物，一种生产该化合物的方法，含有该新型化合物的有机半导体材料以及有机半导体器件。该新型化合物由以下通用式（1）、（2）、（3）或（4）表示（其中Z代表硫原子或硒原子，R代表通常式中的氢原子、烷基或苯基），具有两个萘烯环与噻吩环和硒吩环分别结合的结构。这些化合物在分子中具有共轭系统，由于轨道之间的相互作用，通过每个分子中噻吩环或硒吩环中含有的硫原子或硒原子显示出强烈的分子间相互作用，从而具有良好的场效率。