5,6-bis(octyloxy)-1H-benzo[d][1,2,3]triazole | 1563332-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 5,6-bis(octyloxy)-1H-benzo[d][1,2,3]triazole
• CAS: 1563332-19-3
• 化学式: C₂₂H₃₇N₃O₂
• 分子量: 375.555
• InChiKey: OPKYSCYJBBHJJG-UHFFFAOYSA-N

物化性质

• 沸点：
  530.2±30.0 °C(predicted)
• 密度：
  1.022±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  1-溴辛烷 、 5,6-bis(octyloxy)-1H-benzo[d][1,2,3]triazole 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 以42.8%的产率得到2-octyl-5,6-bis(octyloxy)-2H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Benzotriazole-Containing Planar Conjugated Polymers with Noncovalent Conformational Locks for Thermally Stable and Efficient Polymer Field-Effect Transistors

  摘要：

  We report a series of benzotriazole-based semicrystalline pi-conjugated polymers with noncovalent conformational locks for applications in polymer field-effect transistors. The benzotriazole moiety is a versatile electron-deficient building block that offers two chemically functionalizable sites, 2(N) and 5, 6(C) positions,. allowing easy modulation of the solution processability and electronic structures of the resulting polymers. Fluorine or alkoxy substituents were introduced to the benzotriazole unit to enhance the molecular ordering through intra- and intermolecular F center dot center dot center dot S, F center dot center dot center dot H-C, C-F center dot center dot center dot pi(F), or S center dot center dot center dot O attractive interactions. The fluorinated polymer (PTBTz-F) showed remarkably enhanced hole mobility (mu(h) = 1.9 cm(2)/(V.S), on/off ratio = 8 x 10(7)) upon thermal annealing at 305 degrees C, compared to the unsubstituted one (PTBTz) (mu(h) = 7.0 x 10(-3) cm(2)/(V.s), on/off ratio = 3 x 10(6)). Alkoxy unit substitution (PTBTz-OR) also improved the carrier mobility up to 0.019 cm(2)/(V.s) with an on/off ratio of 4 x 10(5). Fluorine or alkoxy substitution induced tight interchain ordering with edge-on orientation, as confirmed by X-ray diffraction measurements. In particular, fluorinated PTBTz-F showed high thermal stability (T-d 453 degrees C) and the remarkable device characteristics with deep frontier orbital levels.

  DOI：

  10.1021/cm4042346
• 作为产物：
  描述：

  4,5-bis(octyloxy)benzene-1,2-diaminium chloride 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以90.8%的产率得到5,6-bis(octyloxy)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Benzotriazole-Containing Planar Conjugated Polymers with Noncovalent Conformational Locks for Thermally Stable and Efficient Polymer Field-Effect Transistors

  摘要：

  We report a series of benzotriazole-based semicrystalline pi-conjugated polymers with noncovalent conformational locks for applications in polymer field-effect transistors. The benzotriazole moiety is a versatile electron-deficient building block that offers two chemically functionalizable sites, 2(N) and 5, 6(C) positions,. allowing easy modulation of the solution processability and electronic structures of the resulting polymers. Fluorine or alkoxy substituents were introduced to the benzotriazole unit to enhance the molecular ordering through intra- and intermolecular F center dot center dot center dot S, F center dot center dot center dot H-C, C-F center dot center dot center dot pi(F), or S center dot center dot center dot O attractive interactions. The fluorinated polymer (PTBTz-F) showed remarkably enhanced hole mobility (mu(h) = 1.9 cm(2)/(V.S), on/off ratio = 8 x 10(7)) upon thermal annealing at 305 degrees C, compared to the unsubstituted one (PTBTz) (mu(h) = 7.0 x 10(-3) cm(2)/(V.s), on/off ratio = 3 x 10(6)). Alkoxy unit substitution (PTBTz-OR) also improved the carrier mobility up to 0.019 cm(2)/(V.s) with an on/off ratio of 4 x 10(5). Fluorine or alkoxy substitution induced tight interchain ordering with edge-on orientation, as confirmed by X-ray diffraction measurements. In particular, fluorinated PTBTz-F showed high thermal stability (T-d 453 degrees C) and the remarkable device characteristics with deep frontier orbital levels.

  DOI：

  10.1021/cm4042346