2,7-diphenylnaphtho[2,3-b:6,7-b']difuran | 1352544-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2,7-diphenylnaphtho[2,3-b:6,7-b']difuran
• 英文别名: 2,7-Diphenyl-[1]benzofuro[6,5-f][1]benzofuran；2,7-diphenyl-[1]benzofuro[6,5-f][1]benzofuran
• CAS: 1352544-10-5
• 化学式: C₂₆H₁₆O₂
• 分子量: 360.412
• InChiKey: MKYWDQCQKZMFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三(五氟苯基)硼烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,7-diphenylnaphtho[2,3-b:6,7-b']difuran
  参考文献：
  名称：

  Single-Crystal Organic Field-Effect Transistors of Naphthodifurans

  摘要：

  三种类型的萘并二呋喃 (NDF) 被设计为有机场效应晶体管 (OFET) 中的活性有机材料，其中一种萘并[2,1-b:6,5-b']二呋喃被发现可以显示出高达 3.6 cm2 V−1 s−1 的出色 OFET 迁移率。基于晶体堆积结构和理论分析，我们将NDF衍生物的高载流子迁移率归因于大的分子间相互作用和小的重组能。 NDF 化合物表现出非常高的热稳定性和电化学稳定性。结合之前的一些研究，本研究表明稠合呋喃化合物的性能等于或优于相应的噻吩化合物。

  DOI：

  10.1246/bcsj.20150033

文献信息

• 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.
• Single-Crystal Organic Field-Effect Transistors of Naphthodifurans
  作者：Chikahiko Mitsui、Junshi Soeda、Kazumoto Miwa、Kazutaka Shoyama、Yoshinori Ota、Hayato Tsuji、Jun Takeya、Eiichi Nakamura

  DOI：10.1246/bcsj.20150033

  日期：2015.6.15

  Three types of naphthodifurans (NDFs) have been designed as active organic materials in organic field-effect transistors (OFETs), and one of them, naphtho[2,1-b:6,5-b′]difuran, has been found to show an excellent OFET mobility of up to 3.6 cm2 V−1 s−1. Based on the crystal-packing structure and theoretical analyses, we attribute the high carrier mobility of the NDF derivatives to large intermolecular interactions and small reorganization energies. The NDF compounds show very high thermal and electrochemical stability. Together with some previous studies, the present study indicates that fused furan compounds show a performance that is equal to or better than that of the corresponding thiophene compounds.

  三种类型的萘并二呋喃 (NDF) 被设计为有机场效应晶体管 (OFET) 中的活性有机材料，其中一种萘并[2,1-b:6,5-b']二呋喃被发现可以显示出高达 3.6 cm2 V−1 s−1 的出色 OFET 迁移率。基于晶体堆积结构和理论分析，我们将NDF衍生物的高载流子迁移率归因于大的分子间相互作用和小的重组能。 NDF 化合物表现出非常高的热稳定性和电化学稳定性。结合之前的一些研究，本研究表明稠合呋喃化合物的性能等于或优于相应的噻吩化合物。