1,3-di(4-n-hexadecanoxyphenyl)propane-1,3-dione | 816453-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-di(4-n-hexadecanoxyphenyl)propane-1,3-dione
• 英文别名: 1,3-Bis[4-(hexadecyloxy)phenyl]propane-1,3-dione；1,3-bis(4-hexadecoxyphenyl)propane-1,3-dione
• CAS: 816453-83-5
• 化学式: C₄₇H₇₆O₄
• 分子量: 705.118
• InChiKey: ISYNZFXBYCDILD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  51
• 可旋转键数：
  36
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-di(4-n-hexadecanoxyphenyl)propane-1,3-dione 在 四氟硼酸-二乙醚络合物 、 sodium hydride 作用下， 以 二氯甲烷 、 mineral oil 为溶剂， 反应 24.0h， 以50%的产率得到[1,3-di(4-n-hexadecanoxyphenyl)propane-1,3-dionato]difluoroboron(III)
  参考文献：
  名称：

  Alkoxy-substituted difluoroboron benzoylmethanes for photonics applications: A photophysical and spectroscopic study

  摘要：

  本研究制备了两个系列的新型二氟化硼加合物（BDFs），即[BF2(OOR(n))]（类型 I）和[BF2(OO2R(n))]（类型 II）（R = C6H4OCnH2n+1; n = 10-18），它们分别含有在β-二酮酸酯核的 1 位或 1,3 位上带有 4-烷氧基苯基取代基的β-二酮酸酯配体。根据红外光谱数据推断，它们都显示出配体与 BF2 基团之间的强烈相互作用，以及强烈的蓝紫色发射（λmaxem 为 400 至 440 nm），在稀释的二氯甲烷溶液中，荧光量子产率分别为 0.69 至 0.84（I 型）和 0.48 至 0.66（II 型），荧光寿命分别为 1.7 和 2.2 ns。I 和 II 系列染料的光物理特性与溶剂极性和烷氧基苯基取代基的链长无关。此外，即使在强烈的激光照射下，它们也表现出很高的光稳定性。与之前的解释不同，我们的详细光物理和光谱研究排除了准分子形成的可能性，即使在高浓度溶液或固态下也是如此，这表明这些染料具有抗自聚集性。所有这些特点都为这种荧光团在有机发光二极管、固体染料激光器、化学传感器和双光子生物标签等领域的应用铺平了道路。

  DOI：

  10.1039/c0dt00588f

文献信息

• Reactivity of bis(long chain substituted β-diketonato)palladium(II) [Pd(OOR2)2] towards HBF4: formation of luminescent [BF2(OOR2)] derivatives. X-ray structure of [1,3-di(4-n-butoxyphenyl)propane-1,3-dionato]difluoroboron(III)
  作者：M.J. Mayoral、M. Cano、J.A. Campo、J.V. Heras、E. Pinilla、M.R. Torres

  DOI：10.1016/j.inoche.2004.06.011

  日期：2004.8

  Reactions of [Pd(OOR2)(2)] (OOR2 = 1,3-di(4-n-alkyloxyphenyl)propane-1,3-dionato; R = C6H4OCnH2n+1, n = 14, 16, 4) with N,N'-bidentate ligands of the type bis(4-n-alkyloxyphenyl)-1-(pyridin-2-yl)-1H-pyrazoI (pypz(R2)) in the presence of HBF4 gave rise to new dioxoborane derivatives [BF2(OOR2)](1-3) as major products. Compounds 1-3 were also isolated by reaction of [Pd(OOR2)(2)] and HBF4, as well as by reaction of the corresponding beta-diketones or sodium beta-diketonates with HBF4. The new oxoboranes [BF2(OOR2)] (1-3) showed intense yellow or blue luminescence in the solid state and in the solution, respectively. The X-ray structure of 3 containing the shortest chain (R = C6H4OC4H9) evidenced the chelating coordination of the beta-diketonate ligand to the acceptor BF2 group in a boron tetrahedral environment. The molecules were packed in layers showing weak C-(HF)-F-... bifurcated interactions, which were responsible for a bi-dimensional network. (C) 2004 Elsevier B.V. All rights reserved.
• Alkoxy-substituted difluoroboron benzoylmethanes for photonics applications: A photophysical and spectroscopic study
  作者：María José Mayoral、Paloma Ovejero、Mercedes Cano、Guillermo Orellana

  DOI：10.1039/c0dt00588f

  日期：——

  Two series of novel boron difluoride adducts (BDFs), namely [BF2(OOR(n))] (type I) and [BF2(OO2R(n))] (type II) (R = C6H4OCnH2n+1; n = 10–18), containing β-diketonate ligands bearing 4-alkoxyphenyl substituents in position 1 or in positions 1,3 of the β-diketonate core, respectively, have been prepared. All of them display a strong interaction between the ligand and the BF2 group, as deduced from the IR spectroscopic data, and strong blue-violet emission (λmaxem from 400 to 440 nm), with fluorescence quantum yields from 0.69 to 0.84 (type I) and 0.48 to 0.66 (type II) and fluorescence lifetimes of 1.7 and 2.2 ns in diluted dichloromethane solution, respectively. The photophysical properties of I and II series of dyes are independent of the solvent polarity and the chain length of the alkoxyphenyl substituent(s). Moreover, they exhibit high photostability even under intense laser light. Contradicting previous interpretations, our detailed photophysical and spectroscopic study rules out excimer formation even in highly concentrated solution or in the solid state, demonstrating the resistance of these dyes to self-aggregation. All those features pave the way to the application of such fluorophores in OLEDs, solid dye lasers, chemical sensors and two-photon biological labels, to name a few.

  本研究制备了两个系列的新型二氟化硼加合物（BDFs），即[BF2(OOR(n))]（类型 I）和[BF2(OO2R(n))]（类型 II）（R = C6H4OCnH2n+1; n = 10-18），它们分别含有在β-二酮酸酯核的 1 位或 1,3 位上带有 4-烷氧基苯基取代基的β-二酮酸酯配体。根据红外光谱数据推断，它们都显示出配体与 BF2 基团之间的强烈相互作用，以及强烈的蓝紫色发射（λmaxem 为 400 至 440 nm），在稀释的二氯甲烷溶液中，荧光量子产率分别为 0.69 至 0.84（I 型）和 0.48 至 0.66（II 型），荧光寿命分别为 1.7 和 2.2 ns。I 和 II 系列染料的光物理特性与溶剂极性和烷氧基苯基取代基的链长无关。此外，即使在强烈的激光照射下，它们也表现出很高的光稳定性。与之前的解释不同，我们的详细光物理和光谱研究排除了准分子形成的可能性，即使在高浓度溶液或固态下也是如此，这表明这些染料具有抗自聚集性。所有这些特点都为这种荧光团在有机发光二极管、固体染料激光器、化学传感器和双光子生物标签等领域的应用铺平了道路。