naphtho[2,3-b:6,7-b']diselenophene | 928240-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho[2,3-b:6,7-b']diselenophene
• 英文别名: [1]Benzoselenolo[6,5-f][1]benzoselenole；[1]benzoselenolo[6,5-f][1]benzoselenole
• CAS: 928240-91-9
• 化学式: C₁₄H₈Se₂
• 分子量: 334.138
• InChiKey: GFMAEEBBVLSJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  16
• 可旋转键数：
  0
• 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

• 作为产物：
  描述：

  2,6-dibromo-3,7-bis(trimethylsilylethynyl)naphthalene 在 N-甲基吡咯烷酮 、 selenium 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以30%的产率得到naphtho[2,3-b:6,7-b']diselenophene
  参考文献：
  名称：

  Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

  摘要：

  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.

  DOI：

  10.1021/cm202853b

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.