1,3,6-tributylpyrene | 1425542-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,3,6-tributylpyrene
• 英文别名: 1,3,6-Tributylpyrene
• CAS: 1425542-91-1
• 化学式: C₂₈H₃₄
• 分子量: 370.578
• InChiKey: XSTJDKUFMCZQHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1,1-二氯甲醚 、 1,3,6-tributylpyrene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到3,6,8-tributylpyrene-1-carbaldehyde
  参考文献：
  名称：

  具有增强的荧光量子产率和独特的开/关切换特性的弱供体烷基功能化推挽P染料的设计

  摘要：

  我们通过掺入弱推挽部分来设计，合成和评估对环境敏感的溶剂化荧光染料。推的量子产率（烷基）-pull（甲酰基）芘染料受到显着通过引入烷基的成formylpyrene（1- formylpyrene增强：Φ ˚F = 0.10; 3,6,8-三-正-丁基-1- -formylpyrene：Φ ˚F = 0.90;在MeOH中）。新的染料表现出对溶剂的极性和氢键给体能力独特灵敏度和特异性荧光接通/关性能（例如，3,6,8-三-正-丁基-1- formylpyrene：Φ ˚F分别在己烷，氯仿，DMSO和MeOH中分别为0.004、0.80、0.37和0.90）。在此，烷基充当弱的供体，通过破坏1-甲酰基py的HOMO的稳定性来抑制系统间的穿越，同时保持弱的分子内电荷转移性质。通过使用烷基作为弱供体，将来可能会开发出对环境敏感的材料，尤其是对pH敏感的荧光材料。

  DOI：

  10.1002/asia.201402088
• 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 12.5h， 生成 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

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.
• Design of Weak-Donor Alkyl-Functionalized Push-Pull Pyrene Dyes Exhibiting Enhanced Fluorescence Quantum Yields and Unique On/Off Switching Properties
  作者：Yosuke Niko、Shunsuke Sasaki、Susumu Kawauchi、Katsumi Tokumaru、Gen-ichi Konishi

  DOI：10.1002/asia.201402088

  日期：2014.7

  We designed, synthesized, and evaluated environmentally responsive solvatochromic fluorescent dyes by incorporating weak push–pull moieties. The quantum yields of the push (alkyl)–pull (formyl) pyrene dyes were dramatically enhanced by the introduction of alkyl groups into formylpyrene (1‐formylpyrene: ΦF=0.10; 3,6,8‐tri‐n‐butyl‐1‐formylpyrene: ΦF=0.90; in MeOH). The new dyes exhibited unique sensitivity

  我们通过掺入弱推挽部分来设计，合成和评估对环境敏感的溶剂化荧光染料。推的量子产率（烷基）-pull（甲酰基）芘染料受到显着通过引入烷基的成formylpyrene（1- formylpyrene增强：Φ ˚F = 0.10; 3,6,8-三-正-丁基-1- -formylpyrene：Φ ˚F = 0.90;在MeOH中）。新的染料表现出对溶剂的极性和氢键给体能力独特灵敏度和特异性荧光接通/关性能（例如，3,6,8-三-正-丁基-1- formylpyrene：Φ ˚F分别在己烷，氯仿，DMSO和MeOH中分别为0.004、0.80、0.37和0.90）。在此，烷基充当弱的供体，通过破坏1-甲酰基py的HOMO的稳定性来抑制系统间的穿越，同时保持弱的分子内电荷转移性质。通过使用烷基作为弱供体，将来可能会开发出对环境敏感的材料，尤其是对pH敏感的荧光材料。