4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diylbis(thiophene-5,2-diyl))bis(N,N-bis(4-methoxyphenyl)aniline) | 1380314-79-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diylbis(thiophene-5,2-diyl))bis(N,N-bis(4-methoxyphenyl)aniline)
• 英文别名: 4-[5-[4-[5-[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]-N,N-bis(4-methoxyphenyl)aniline
• CAS: 1380314-79-3
• 化学式: C₅₄H₄₂N₄O₄S₃
• 分子量: 907.15
• InChiKey: OILPYTVNZZRBPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  65
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4,4'-二甲氧基二苯胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 potassium acetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 64.0h， 生成 4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diylbis(thiophene-5,2-diyl))bis(N,N-bis(4-methoxyphenyl)aniline)
  参考文献：
  名称：

  Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials

  摘要：

  The synthesized benzothiadiazole-based series fluorophores as potential wavelength-shifting materials exhibit large Stokes shifts (>160 nm) with multiple broad absorbance bands from UV region to 600 nm and a strong fluorescence peak around 700 nm (in CHCI3). Intramolecular charge transfer (ITC) characters of the synthesized compounds are examined using UV-vis and photoluminescence solvatochromic shift measurements. Among the synthesized compounds, the fluorophores with asymmetrical structures exhibit larger Stokes shifts than those with symmetrical structures due to large dipole moment changes upon excitation. The fluorophores with electron-donating methoxyl groups attached to the triphenylamine donors are found to have strong ICT properties. Photophysical experimental results are supported by theoretical calculations using Density Function Theory (DFT) and Time Dependent Density Function Theory (TD-DFT) methods. Calculated frontier molecular orbitals (MOs) of ground states on these fluorophores showed an increase in ICT character up to 50% from HOMO to LUMO. Geometric optimization calculations of the excited state reveal that these fluorophores show a more planar structure for the excited state than the ground state, which allows more pi-pi* overlap and leads to larger Stokes shifts and higher quantum yields. Published by Elsevier B.V.

  DOI：

  10.1016/j.jphotochem.2012.01.011

文献信息

• 一种非螺型有机小分子空穴传输材料的分子平面性增强方法
  申请人：中国科学院合肥物质科学研究院

  公开号：CN112266383B

  公开（公告）日：2022-05-10

  本发明公开了一种非螺型有机小分子空穴传输材料的分子平面性增强方法，涉及光电材料技术领域，是在非螺型有机小分子的分子内相邻基团间引入近程分子内相互作用。本发明通过在分子内引入近程分子内相互作用，减小分子中相邻基团的二面角，增强分子平面性，相较于无近程分子内相互作用的分子，有效增强分子间的π‑π堆积，提高空穴迁移率。
• Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials
  作者：Yilin Li、Louis Scudiero、Tianhui Ren、Wen-Ji Dong

  DOI：10.1016/j.jphotochem.2012.01.011

  日期：2012.3

  The synthesized benzothiadiazole-based series fluorophores as potential wavelength-shifting materials exhibit large Stokes shifts (>160 nm) with multiple broad absorbance bands from UV region to 600 nm and a strong fluorescence peak around 700 nm (in CHCI3). Intramolecular charge transfer (ITC) characters of the synthesized compounds are examined using UV-vis and photoluminescence solvatochromic shift measurements. Among the synthesized compounds, the fluorophores with asymmetrical structures exhibit larger Stokes shifts than those with symmetrical structures due to large dipole moment changes upon excitation. The fluorophores with electron-donating methoxyl groups attached to the triphenylamine donors are found to have strong ICT properties. Photophysical experimental results are supported by theoretical calculations using Density Function Theory (DFT) and Time Dependent Density Function Theory (TD-DFT) methods. Calculated frontier molecular orbitals (MOs) of ground states on these fluorophores showed an increase in ICT character up to 50% from HOMO to LUMO. Geometric optimization calculations of the excited state reveal that these fluorophores show a more planar structure for the excited state than the ground state, which allows more pi-pi* overlap and leads to larger Stokes shifts and higher quantum yields. Published by Elsevier B.V.