4-[2-[4-Bromo-5-[3-bromo-5-[2-(4-cyanophenyl)ethynyl]thiophen-2-yl]thiophen-2-yl]ethynyl]benzonitrile | 910796-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4-[2-[4-Bromo-5-[3-bromo-5-[2-(4-cyanophenyl)ethynyl]thiophen-2-yl]thiophen-2-yl]ethynyl]benzonitrile
• 英文别名: 4-[2-[4-bromo-5-[3-bromo-5-[2-(4-cyanophenyl)ethynyl]thiophen-2-yl]thiophen-2-yl]ethynyl]benzonitrile
• CAS: 910796-83-7
• 化学式: C₂₆H₁₀Br₂N₂S₂
• 分子量: 574.319
• InChiKey: QOXWYTAAXPRNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-[4-Bromo-5-[3-bromo-5-[2-(4-cyanophenyl)ethynyl]thiophen-2-yl]thiophen-2-yl]ethynyl]benzonitrile 、 4-甲苯基乙炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 反应 48.0h， 以26%的产率得到4-[2-[5-[5-[2-(4-Cyanophenyl)ethynyl]-3-[2-(4-methylphenyl)ethynyl]thiophen-2-yl]-4-[2-(4-methylphenyl)ethynyl]thiophen-2-yl]ethynyl]benzonitrile
  参考文献：
  名称：

  Two-photon absorption chromophores with a tunable [2,2′]bithiophene core

  摘要：

  Sonogashira coupling between 3,5,3',5'-tetrabromo-[2,2']bithiophene and various terminal alkynes provides two-photon absorption (TPA) chromophores 1-6, which possess electron donor (D) and/or acceptor (A) alkynyl substituents at 3(3') and 5(5') sites of the bithiophene core. The up-converted fluorescence emission excited at 800 nn (Ti:sapphire femtosecond laser, similar to 100 fs pulses) was used to determine the two-photon absorption cross-sections (Q) of these compounds. The corresponding TPA cross-section (a) values ranging from 132 to 1120 GM (10(-50) cm(4)s photon(-1)) can be fine-tuned by the substitutents. The quadrupolar-type (A-pi-D-pi-A) chromophore 5 exhibits the largest Q value (1120 GM) in CH2Cl2 upon 800 nm excitation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.085
• 作为产物：
  描述：

  3,3',5,5'-四溴-2,2'-联噻吩 、 4-乙炔基苯甲腈 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 反应 24.0h， 以60%的产率得到4-[2-[4-Bromo-5-[3-bromo-5-[2-(4-cyanophenyl)ethynyl]thiophen-2-yl]thiophen-2-yl]ethynyl]benzonitrile
  参考文献：
  名称：

  Two-photon absorption chromophores with a tunable [2,2′]bithiophene core

  摘要：

  Sonogashira coupling between 3,5,3',5'-tetrabromo-[2,2']bithiophene and various terminal alkynes provides two-photon absorption (TPA) chromophores 1-6, which possess electron donor (D) and/or acceptor (A) alkynyl substituents at 3(3') and 5(5') sites of the bithiophene core. The up-converted fluorescence emission excited at 800 nn (Ti:sapphire femtosecond laser, similar to 100 fs pulses) was used to determine the two-photon absorption cross-sections (Q) of these compounds. The corresponding TPA cross-section (a) values ranging from 132 to 1120 GM (10(-50) cm(4)s photon(-1)) can be fine-tuned by the substitutents. The quadrupolar-type (A-pi-D-pi-A) chromophore 5 exhibits the largest Q value (1120 GM) in CH2Cl2 upon 800 nm excitation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.085

文献信息

• Two-photon absorption chromophores with a tunable [2,2′]bithiophene core
  作者：Chia-Feng Chou、Tai-Hsiang Huang、Jiann T. Lin、Cheng-chih Hsieh、Chin-Hung Lai、Pi-Tai Chou、Chiitang Tsai

  DOI：10.1016/j.tet.2006.06.085

  日期：2006.9

  Sonogashira coupling between 3,5,3',5'-tetrabromo-[2,2']bithiophene and various terminal alkynes provides two-photon absorption (TPA) chromophores 1-6, which possess electron donor (D) and/or acceptor (A) alkynyl substituents at 3(3') and 5(5') sites of the bithiophene core. The up-converted fluorescence emission excited at 800 nn (Ti:sapphire femtosecond laser, similar to 100 fs pulses) was used to determine the two-photon absorption cross-sections (Q) of these compounds. The corresponding TPA cross-section (a) values ranging from 132 to 1120 GM (10(-50) cm(4)s photon(-1)) can be fine-tuned by the substitutents. The quadrupolar-type (A-pi-D-pi-A) chromophore 5 exhibits the largest Q value (1120 GM) in CH2Cl2 upon 800 nm excitation. (c) 2006 Elsevier Ltd. All rights reserved.