2-(thiophen-3-yl)ethyl 4-(pyren-1-yl)butanoate | 1422255-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-(thiophen-3-yl)ethyl 4-(pyren-1-yl)butanoate
• 英文别名: 2-Thiophen-3-ylethyl 4-pyren-1-ylbutanoate
• CAS: 1422255-37-5
• 化学式: C₂₆H₂₂O₂S
• 分子量: 398.525
• InChiKey: CWIOIGYAPGVAOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(thiophen-3-yl)ethyl 4-(pyren-1-yl)butanoate 在 iron(III) chloride 、 ammonium hydroxide 作用下， 以 氯仿 、 甲醇 为溶剂， 反应 12.0h， 以68%的产率得到
  参考文献：
  名称：

  含芘发色团的新型聚噻吩的合成与表征：热、光和电化学性质

  摘要：

  合成了一系列含有噻吩单体 TPM1-5 的新型芘，并通过 FTIR、MS、1H-和 13C-NMR 光谱进行了充分表征；它们的热性能由 TGA 和 DSC 确定。这些单体使用 FeCl3 作为氧化剂进行化学聚合，得到相应的低聚物 TPO1-5)，然后通过电化学聚合得到相应的聚合物薄膜沉积在 ITO 上。所有低聚物都表现出良好的热稳定性，T10 值在 255 到 299 °C 之间，Tg 值在 36 到 39 °C 之间变化。由于芘基团的 S0 → S2 跃迁，单体在 345 nm 处显示出吸收带，而荧光光谱显示出由 375-420 nm 处的“单体”发射产生的宽发射带。所得聚合物在 244 和 354 nm 处表现出两个吸收带，分别是由于聚噻吩和芘部分。由于这些化合物中存在分子内芘-芘相互作用，聚合物的荧光光谱在 380-420 nm 处显示出宽的“单体”发射，然后在 570 nm 处出现强烈的准分子发射带。

  DOI：

  10.3390/molecules21020172
• 作为产物：
  描述：

  噻吩-3-乙醇 、 1-芘丁酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以82%的产率得到2-(thiophen-3-yl)ethyl 4-(pyren-1-yl)butanoate
  参考文献：
  名称：

  含芘发色团的新型聚噻吩的合成与表征：热、光和电化学性质

  摘要：

  合成了一系列含有噻吩单体 TPM1-5 的新型芘，并通过 FTIR、MS、1H-和 13C-NMR 光谱进行了充分表征；它们的热性能由 TGA 和 DSC 确定。这些单体使用 FeCl3 作为氧化剂进行化学聚合，得到相应的低聚物 TPO1-5)，然后通过电化学聚合得到相应的聚合物薄膜沉积在 ITO 上。所有低聚物都表现出良好的热稳定性，T10 值在 255 到 299 °C 之间，Tg 值在 36 到 39 °C 之间变化。由于芘基团的 S0 → S2 跃迁，单体在 345 nm 处显示出吸收带，而荧光光谱显示出由 375-420 nm 处的“单体”发射产生的宽发射带。所得聚合物在 244 和 354 nm 处表现出两个吸收带，分别是由于聚噻吩和芘部分。由于这些化合物中存在分子内芘-芘相互作用，聚合物的荧光光谱在 380-420 nm 处显示出宽的“单体”发射，然后在 570 nm 处出现强烈的准分子发射带。

  DOI：

  10.3390/molecules21020172

文献信息

• Synthesis, electrochemistry and fluorescence behavior of thiophene derivatives decorated with coumarin, pyrene and naphthalene moieties
  作者：A.S. Abd-El-Aziz、S. Dalgakiran、I. Kucukkaya、B.D. Wagner

  DOI：10.1016/j.electacta.2012.11.082

  日期：2013.2

  A novel series of functionalized thiophenes incorporating coumarin, pyrene and naphthalene pendants were synthesized by Steglich esterification in the presence of DCC/DMAP (dicyclohexylcarbodiimide/N,N-dimethylaminopyridine) and the synthesized monomers were electrochemically deposited onto glassy carbon and carbon fiber micro electrodes as active electrode materials. The synthesized thiophene derivatives were characterized by H-1 NMR, C-13 NMR, FTIR, cyclic voltammetry, electrochemical impedance spectroscopy and electronic absorption as well as fluorescence spectroscopy. An electrochemical impedance study was performed on the surface modified electrodes. Variation of capacitance values was explained according to the different fluorophore groups attached to the thiophene as well as the different substrates. The fluorescence properties of the three compounds in dimethylsulfoxide were measured, with varying effects of the thiophene moiety on the fluorescence emission. The morphology of the monomers was monitored using SEM. (C) 2012 Elsevier Ltd. All rights reserved.
• Polythiophenes based on pyrene as pendant group: Synthesis, structural characterization and luminescent properties
  作者：E. González-Juárez、M. Güizado-Rodríguez、V. Barba、M. Melgoza-Ramírez、M. Rodríguez、G. Ramos-Ortíz、J.L. Maldonado

  DOI：10.1016/j.molstruc.2015.09.011

  日期：2016.1

  Novel polythiophenes (PTs) derived from 3-alkylthiophenes (R = hexyl, octyl) and a thiophene functionalized with pyrene chromophore were synthesized. A homopolymer and copolymers were obtained by using different stoichiometric ratios, and their photophysical properties were investigated. Physicochemically characterized by FT-IR, H-1 NMR, UV-vis, DSC-TGA and GPC as well as fluorescence spectroscopy, the new PTs reached moderate molecular weight distributions, exhibited good thermal properties and were easily processable for depositing films of satisfactory optical quality with third-order nonlinear optical susceptibilities of approximately 10(-12) esu. The new PTs showed absorption and emission bands ranging from 346 to 430 nm, and from 450 to 570 nm, respectively, with quantum yields between 0.07 and 0.25. In addition, nanoparticles were obtained from the N's by using the miniemulsion technique. Their spectroscopic characteristics and morphology were determined by means of UV vis spectroscopy and SEM analysis. (C) 2015 Elsevier B.V. All rights reserved.