3-(trimethylsilylbutadiynyl)perylene | 1379596-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-(trimethylsilylbutadiynyl)perylene
• 英文别名: Trimethyl(4-perylen-3-ylbuta-1,3-diynyl)silane；trimethyl(4-perylen-3-ylbuta-1,3-diynyl)silane
• CAS: 1379596-27-6
• 化学式: C₂₇H₂₀Si
• 分子量: 372.541
• InChiKey: CZYBUGNFIBXPIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3-(trimethylsilylbutadiynyl)perylene 、 3′,5′-bis-O-propionyl-5-iodo-2′-deoxyuridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到3′,5′-bis-O-propionyl-5-(perylen-3-ylbutadiynyl)-2′-deoxyuridine
  参考文献：
  名称：

  Fluorescent nucleosides with an elongated rigid linker: attaching perylene to a nucleobase via a one-pot desilylation/Sonogashira reaction

  摘要：

  Two novel analogues of the highly fluorescent and potent antiviral compound, 5-(perylen-3-ylethynyl)-2'-deoxyuridine, containing elongated rigid linkers, butadiyne and 1,4-diethynylphenylene, were synthesized from the corresponding trimethylsilyl alkynes using a one-pot desilylation/Sonogashira reaction as the key step. Their spectral properties are compared to those of the parent perylenylethynyl nucleoside. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2016.09.050
• 作为产物：
  描述：

  3-溴芘 在 copper(l) iodide 、 四(三苯基膦)钯 、 四甲基乙二胺 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 3-(trimethylsilylbutadiynyl)perylene
  参考文献：
  名称：

  Substitution effects of C C triple bonds on the fluorescent properties of perylenes studied by emission and transient absorption measurements

  摘要：

  Perylenes substituted with trimethylsilylethynyl, tert-butylethynyl and trimethylsilylbutadiynyl groups were prepared, and their photophysical and photochemical properties were investigated through measurements of fluorescence yields, lifetimes, and triplet-triplet absorption. Introduction of these groups caused little change in the rates of fluorescence, but decreased the fluorescence yields and substantially enhanced the rates of non-radiative processes. Observation of the triplet absorption was evident for the origin of the enhanced non-radiative process by the substitution with the triple bond(s). (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cplett.2012.03.108

文献信息

• Substitution effects of C C triple bonds on the fluorescent properties of perylenes studied by emission and transient absorption measurements
  作者：Minoru Yamaji、Hajime Maeda、Yasuaki Nanai、Kazuhiko Mizuno

  DOI：10.1016/j.cplett.2012.03.108

  日期：2012.5

  Perylenes substituted with trimethylsilylethynyl, tert-butylethynyl and trimethylsilylbutadiynyl groups were prepared, and their photophysical and photochemical properties were investigated through measurements of fluorescence yields, lifetimes, and triplet-triplet absorption. Introduction of these groups caused little change in the rates of fluorescence, but decreased the fluorescence yields and substantially enhanced the rates of non-radiative processes. Observation of the triplet absorption was evident for the origin of the enhanced non-radiative process by the substitution with the triple bond(s). (C) 2012 Elsevier B. V. All rights reserved.
• Fluorescent nucleosides with an elongated rigid linker: attaching perylene to a nucleobase via a one-pot desilylation/Sonogashira reaction
  作者：Alexey A. Chistov、Nikita M. Ivanov、Sergey V. Kutyakov、Alexey V. Ustinov、Anton V. Glybin、Philipp P. Streshnev、Irina V. Mikhura、Vladimir A. Korshun

  DOI：10.1016/j.tetlet.2016.09.050

  日期：2016.10

  Two novel analogues of the highly fluorescent and potent antiviral compound, 5-(perylen-3-ylethynyl)-2'-deoxyuridine, containing elongated rigid linkers, butadiyne and 1,4-diethynylphenylene, were synthesized from the corresponding trimethylsilyl alkynes using a one-pot desilylation/Sonogashira reaction as the key step. Their spectral properties are compared to those of the parent perylenylethynyl nucleoside. (C) 2016 Published by Elsevier Ltd.