4,4'-dibromo-2,2'-diethynyl-1,1'-biphenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-dibromo-2,2'-diethynyl-1,1'-biphenyl
• 英文别名: 4-Bromo-1-(4-bromo-2-ethynylphenyl)-2-ethynylbenzene；4-bromo-1-(4-bromo-2-ethynylphenyl)-2-ethynylbenzene
• 化学式: C₁₆H₈Br₂
• 分子量: 360.048
• InChiKey: PUDKASMHODSZBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  4,4'-dibromo-2,2'-diethynyl-1,1'-biphenyl 、 3,4-bis(4-dodecylphenyl)-2,5-diphenylcyclopentadienone 以 邻二甲苯 为溶剂， 反应 24.0h， 以79%的产率得到5'',4'''-dibromo-5',6',3'''',4''''-tetrakis(4-dodecylphenyl)-4',5''''-diphenyl-1,1':2',1'':2'',1''':2''',1'''':2'''',1'''''-sexiphenyl
  参考文献：
  名称：

  Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons

  摘要：

  AbstractGraphene nanoribbons (GNRs) with an unprecedented “necklace‐like” structure were synthesized through a bottom‐up chemical approach, based on the oxidative cyclodehydrogenation of tailor‐made polyphenylene precursors. A polycyclic aromatic hydrocarbon consisting of 84 sp2 carbons (C84) was also synthesized and characterized as a model compound. Characterizations by a combination of MALDI‐TOF MS and FTIR, Raman, and UV/Vis absorption spectroscopy validated the formation of the necklace‐like GNRs. The absorption spectrum and DFT calculations revealed a bandgap of approximately 1.4 eV for this novel GNR system, which has not been attained with other GNR structures, enabling further fine‐tuning of GNR bandgaps by structural modulation.

  DOI：

  10.1002/asia.201500450
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 tin 、 铜 、 copper(II) iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 三乙胺 为溶剂， 反应 39.0h， 生成 4,4'-dibromo-2,2'-diethynyl-1,1'-biphenyl
  参考文献：
  名称：

  Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons

  摘要：

  AbstractGraphene nanoribbons (GNRs) with an unprecedented “necklace‐like” structure were synthesized through a bottom‐up chemical approach, based on the oxidative cyclodehydrogenation of tailor‐made polyphenylene precursors. A polycyclic aromatic hydrocarbon consisting of 84 sp2 carbons (C84) was also synthesized and characterized as a model compound. Characterizations by a combination of MALDI‐TOF MS and FTIR, Raman, and UV/Vis absorption spectroscopy validated the formation of the necklace‐like GNRs. The absorption spectrum and DFT calculations revealed a bandgap of approximately 1.4 eV for this novel GNR system, which has not been attained with other GNR structures, enabling further fine‐tuning of GNR bandgaps by structural modulation.

  DOI：

  10.1002/asia.201500450

文献信息

• [EN] OLIGOPHENYLENE MONOMERS AND POLYMERIC PRECURSORS FOR PRODUCING GRAPHENE NANORIBBONS<br/>[FR] MONOMÈRES OLIGOPHÉNYLÈNE ET PRÉCURSEURS POLYMÈRES DESTINÉS À PRODUIRE DES NANORUBANS DE GRAPHÈNE
  申请人：BASF SE

  公开号：WO2013061256A1

  公开（公告）日：2013-05-02

  Oligophenylene monomers for the synthesis of polymeric precursors for the preparation of graphene nanoribbons, the polymeric precursors, and methods for preparing them, as well as methods for preparing the graphene nanoribbons from the polymeric precursors and the monomers are provided.

  提供了用于合成聚合物前体以制备石墨烯纳米带的寡苯单体、聚合物前体以及其制备方法，以及从聚合物前体和单体制备石墨烯纳米带的方法。
• OLIGOPHENYLENE MONOMERS AND POLYMERIC PRECURSORS FOR PRODUCING GRAPHENE NANORIBBONS
  申请人：BASF SE

  公开号：US20140301935A1

  公开（公告）日：2014-10-09

  Oligophenylene monomers for the synthesis of polymeric precursors for the preparation of graphene nanoribbons, the polymeric precursors, and methods for preparing them, as well as methods for preparing the graphene nanoribbons from the polymeric precursors and the monomers are provided.

  本发明提供用于合成制备石墨烯纳米带的聚合物前体的寡苯单体，聚合物前体以及其制备方法，以及从聚合物前体和单体制备石墨烯纳米带的方法。
• Bottom-Up Synthesis of Necklace-Like Graphene Nanoribbons
  作者：Matthias Georg Schwab、Akimitsu Narita、Silvio Osella、Yunbin Hu、Ali Maghsoumi、Alexey Mavrinsky、Wojciech Pisula、Chiara Castiglioni、Matteo Tommasini、David Beljonne、Xinliang Feng、Klaus Müllen

  DOI：10.1002/asia.201500450

  日期：2015.10

  AbstractGraphene nanoribbons (GNRs) with an unprecedented “necklace‐like” structure were synthesized through a bottom‐up chemical approach, based on the oxidative cyclodehydrogenation of tailor‐made polyphenylene precursors. A polycyclic aromatic hydrocarbon consisting of 84 sp2 carbons (C84) was also synthesized and characterized as a model compound. Characterizations by a combination of MALDI‐TOF MS and FTIR, Raman, and UV/Vis absorption spectroscopy validated the formation of the necklace‐like GNRs. The absorption spectrum and DFT calculations revealed a bandgap of approximately 1.4 eV for this novel GNR system, which has not been attained with other GNR structures, enabling further fine‐tuning of GNR bandgaps by structural modulation.