3-bromo-1,6-dibutylpyrene | 1425542-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3-bromo-1,6-dibutylpyrene
• 英文别名: 3-Bromo-1,6-dibutylpyrene
• CAS: 1425542-90-0
• 化学式: C₂₄H₂₅Br
• 分子量: 393.367
• InChiKey: IQQXEUBYEDITRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 3-bromo-1,6-dibutylpyrene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以66%的产率得到1,3,6-tributylpyrene
  参考文献：
  名称：

  Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through σ–π Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Positions and Their Photophysical Properties

  摘要：

  We have systematically synthesized 1-, 3-, 6-, and 8-alkyl-substituted pyrene derivatives using the latest synthesis methods and investigated the effects of alkyl substitution on the photophysical properties of the pyrene chromophore. Like the trimethylsilyl group, which is known to enhance the fluorescence properties of some chromophores through sigma*-pi* conjugation, alkyl groups (primary, secondary, and tertiary) enhanced the fluorescence quantum yield of the pyrene chromophore through sigma-pi conjugation in most cases. While these enhancements in the fluorescence quantum yield were beyond expectations, the results were supported by absolute measurements. These results also indicate that ubiquitous alkyl groups can be used to tune the photophysical properties of the pyrene chromophore, as well as to improve the solubility or prevent aggregation. In other words, they can be used to develop new photofunctional materials.

  DOI：

  10.1021/jo400128c
• 作为产物：
  描述：

  1,6-二溴芘 在 正丁基锂 、 氢溴酸 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-bromo-1,6-dibutylpyrene
  参考文献：
  名称：

  Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through σ–π Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Positions and Their Photophysical Properties

  摘要：

  We have systematically synthesized 1-, 3-, 6-, and 8-alkyl-substituted pyrene derivatives using the latest synthesis methods and investigated the effects of alkyl substitution on the photophysical properties of the pyrene chromophore. Like the trimethylsilyl group, which is known to enhance the fluorescence properties of some chromophores through sigma*-pi* conjugation, alkyl groups (primary, secondary, and tertiary) enhanced the fluorescence quantum yield of the pyrene chromophore through sigma-pi conjugation in most cases. While these enhancements in the fluorescence quantum yield were beyond expectations, the results were supported by absolute measurements. These results also indicate that ubiquitous alkyl groups can be used to tune the photophysical properties of the pyrene chromophore, as well as to improve the solubility or prevent aggregation. In other words, they can be used to develop new photofunctional materials.

  DOI：

  10.1021/jo400128c

文献信息

• Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through σ–π Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Positions and Their Photophysical Properties
  作者：Yosuke Niko、Susumu Kawauchi、Shun Otsu、Katsumi Tokumaru、Gen-ichi Konishi

  DOI：10.1021/jo400128c

  日期：2013.4.5

  We have systematically synthesized 1-, 3-, 6-, and 8-alkyl-substituted pyrene derivatives using the latest synthesis methods and investigated the effects of alkyl substitution on the photophysical properties of the pyrene chromophore. Like the trimethylsilyl group, which is known to enhance the fluorescence properties of some chromophores through sigma*-pi* conjugation, alkyl groups (primary, secondary, and tertiary) enhanced the fluorescence quantum yield of the pyrene chromophore through sigma-pi conjugation in most cases. While these enhancements in the fluorescence quantum yield were beyond expectations, the results were supported by absolute measurements. These results also indicate that ubiquitous alkyl groups can be used to tune the photophysical properties of the pyrene chromophore, as well as to improve the solubility or prevent aggregation. In other words, they can be used to develop new photofunctional materials.