Methyl 3-[5-(3-methoxycarbonylnaphthalen-2-yl)naphthalen-1-yl]naphthalene-2-carboxylate | 1608502-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 3-[5-(3-methoxycarbonylnaphthalen-2-yl)naphthalen-1-yl]naphthalene-2-carboxylate
• CAS: 1608502-70-0
• 化学式: C₃₄H₂₄O₄
• 分子量: 496.562
• InChiKey: DOYDWUIFOQUQGT-UHFFFAOYSA-N

物化性质

• 沸点：
  678.5±55.0 °C(predicted)
• 密度：
  1.247±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-[5-(3-methoxycarbonylnaphthalen-2-yl)naphthalen-1-yl]naphthalene-2-carboxylate 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以92%的产率得到3-[5-(3-Carboxynaphthalen-2-yl)naphthalen-1-yl]naphthalene-2-carboxylic acid
  参考文献：
  名称：

  Bistetracene: An Air-Stable, High-Mobility Organic Semiconductor with Extended Conjugation

  摘要：

  We report the synthesis and characterization of "bistetracene", an unconventional, linearly extended conjugated core with eight fused rings. The annellation mode of the system allows for increased stability of the conjugated system relative to linear analogues due to the increased number of Clar aromatic sextets. By attaching the appropriate solubilizing substituents, efficient molecular packing with large transfer integrals can be obtained. The electronic structure calculations suggest these large polycyclic aromatic hydrocarbons (PAHs) exhibit excellent intrinsic charge transport properties. Charge carrier mobilities as large as 6.1 cm(2) V-1 s(-1) and current on/off ratios of 10(7) were determined experimentally for one of our compounds. Our study provides valuable insight into the design of unconventional semiconductor compounds based on higher PAHs for use in high-performance devices.

  DOI：

  10.1021/ja503643s
• 作为产物：
  描述：

  methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate 、 1,5-二溴萘 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到Methyl 3-[5-(3-methoxycarbonylnaphthalen-2-yl)naphthalen-1-yl]naphthalene-2-carboxylate
  参考文献：
  名称：

  Bistetracene: An Air-Stable, High-Mobility Organic Semiconductor with Extended Conjugation

  摘要：

  We report the synthesis and characterization of "bistetracene", an unconventional, linearly extended conjugated core with eight fused rings. The annellation mode of the system allows for increased stability of the conjugated system relative to linear analogues due to the increased number of Clar aromatic sextets. By attaching the appropriate solubilizing substituents, efficient molecular packing with large transfer integrals can be obtained. The electronic structure calculations suggest these large polycyclic aromatic hydrocarbons (PAHs) exhibit excellent intrinsic charge transport properties. Charge carrier mobilities as large as 6.1 cm(2) V-1 s(-1) and current on/off ratios of 10(7) were determined experimentally for one of our compounds. Our study provides valuable insight into the design of unconventional semiconductor compounds based on higher PAHs for use in high-performance devices.

  DOI：

  10.1021/ja503643s

文献信息

• Substituted angular bistetracenes and substituted angular bisoligoacenes and electronic devices made with same
  申请人：University of Massachusetts

  公开号：US10005796B2

  公开（公告）日：2018-06-26

  We report the synthesis and characterization of novel bistetracenes, an unconventional, linearly extended conjugated core with eight fused rings. Also described are bisoligoacenes. In general, the properties and stability of large polycyclic aromatic hydrocarbons (PAHs) strongly depend on the mode of ring annellation and the topology of their it-electron systems, which are usually associated with the resonance stabilization energy in large PAHs.

  我们报告了新型双四烯的合成和特性。双四烯是一种非常规的线性延伸共轭内核，具有八个融合环。此外还介绍了双靛红烯。一般来说，大型多环芳烃（PAHs）的特性和稳定性在很大程度上取决于环的环化模式和其电子系统的拓扑结构，这通常与大型多环芳烃的共振稳定能有关。
• SUBSTITUTED ANGULAR BISTETRACENES AND SUBSTITUTED ANGULAR BISOLIGOACENES AND ELECTRONIC DEVICES MADE WITH SAME
  申请人：University of Massachusetts

  公开号：US20170050991A1

  公开（公告）日：2017-02-23

  We report the synthesis and characterization of novel bistetracenes, an unconventional, linearly extended conjugated core with eight fused rings. Also described are bisoligoacenes. In general, the properties and stability of large polycyclic aromatic hydrocarbons (PAHs) strongly depend on the mode of ring annellation and the topology of their it-electron systems, which are usually associated with the resonance stabilization energy in large PAHs.
• [EN] SUBSTITUTED ANGULAR BISTETRACENES AND SUBSTITUTED ANGULAR BISOLIGOACENES AND ELECTRONIC DEVICES MADE WITH SAME<br/>[FR] BISTÉTRACÈNES ANGULAIRES SUBSTITUÉS ET BISOLIGOACÈNES ANGULAIRES SUBSTITUÉS ET DISPOSITIF ÉLECTRONIQUE FABRIQUÉ AVEC CEUX-CI
  申请人：UNIV MASSACHUSETTS

  公开号：WO2015168638A1

  公开（公告）日：2015-11-05

  We report the synthesis and characterization of novel bistetracenes, an unconventional, linearly extended conjugated core with eight fused rings. Also described are bisoligoacenes. In general, the properties and stability of large polycyclic aromatic hydrocarbons (PAHs) strongly depend on the mode of ring annellation and the topology of their it-electron systems, which are usually associated with the resonance stabilization energy in large PAHs.