1,3,5-tris(4-ethynylphenyl)-1,3,5-triazinane-2,4,6-trione | 1350555-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1,3,5-tris(4-ethynylphenyl)-1,3,5-triazinane-2,4,6-trione
• 英文别名: tris(4-phenylethynyl)isocyanurate；1,3,5-Tris(4-ethynylphenyl)-1,3,5-triazinane-2,4,6-trione
• CAS: 1350555-79-1
• 化学式: C₂₇H₁₅N₃O₃
• 分子量: 429.434
• InChiKey: RNTYDDDLOLPQES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(4-ethynylphenyl)-1,3,5-triazinane-2,4,6-trione 、 2-溴-9,9-二丁基芴 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以60%的产率得到1,3,5-tris(4-(2-(9,9-dibutyl-9H-fluoren-2-yl)ethynyl)phenyl)-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  Triarylisocyanurate‐Based Fluorescent Two‐Photon Absorbers

  摘要：

  AbstractThe synthesis and characterization of six triarylisocyanurates, featuring 2,7‐fluorenyl or 9,10‐anthracenyl groups incorporated in their peripheral arms are reported. Photophysical studies reveal that these new octupolar derivatives are more fluorescent (ΦF≥0.60 for all new compounds except for 1,3,5‐tri(9H‐fluoren‐2‐yl)‐1,3,5‐triazinane‐2,4,6‐trione 3) and present a red‐shifted lowest absorption and emission compared to their known phenyl analogues of comparable size. Depending on the nature of the terminal substituent, fast intramolecular energy transfer among the three arms or localization of the excitation on a single branch occurs after population of their first singlet excited state. The latter effect was only observed in the presence of strongly electron‐releasing substituents in polar media. These new chromophores are also better two‐photon absorbers than the 1,4‐phenylene‐based isocyanurates reported so far, with cross sections σ2≥500 GM at 770 nm for 4‐NPh2 the fluorenyl group containing (13) and the anthracenyl group containing (14) chromophores. All these spectroscopic features, analyzed with the help of quantum chemical calculations, are crucial for the design of new biphotonic fluorescent dyes.

  DOI：

  10.1002/cplu.202000036
• 作为产物：
  描述：

  1,3,5-tris(4-bromophenyl)-1,3,5-triazinane-2,4,6-trione 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,3,5-tris(4-ethynylphenyl)-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  供体基团外围功能化的三芳基-1,3,5-三嗪烷-2,4,6-三酮（异氰脲酸酯）：其线性和非线性光学性质的合成和研究

  摘要：

  本文报道了在外围通过供体臂官能化的一系列异氰脲酸酯的线性光学（LO）和非线性光学（NLO）性质。这些八极衍生物是直接从商业异氰酸酯衍生物获得的，并已进行了充分表征。尽管这些化合物中的几种是已知的，但显示出最大的NLO活性的化合物都是新化合物。在二阶活性方面，这些衍生物中的几种表现出显着的活性/透明度权衡。就三阶活性而言，较长的衍生物具有较强的供体基团（X = NH 2，NMe 2或NPh 2）被证明具有明显的两光子吸收截面。这些强烈发光的衍生物具有高达410 GM的双光子吸收截面。还进行了DFT计算以阐明其电子结构并合理化其NLO特性。据我们所知，本研究首先涉及这些原始环三聚体的非线性光学性质。

  DOI：

  10.1002/chem.201200484

文献信息

• Donor-substituted triaryl-1,3,5-triazinanes-2,4,6-triones: octupolar NLO-phores with a remarkable transparency–nonlinearity trade-off
  作者：Gilles Argouarch、Romain Veillard、Thierry Roisnel、Anissa Amar、Abdou Boucekkine、Anu Singh、Isabelle Ledoux、Frédéric Paul

  DOI：10.1039/c1nj20442d

  日期：——

  We report in this letter the measurement of the hyperpolarizabilities of a series of donor-substituted triaryl-1,3,5-triazinanes-2,4,6-triones by hyper Rayleigh scattering (HRS). A remarkable transparency–nonlinearity trade-off is evidenced for these octupolar NLO-phores which might be accessed in a straightforward synthetic way and in a few steps from commercial isocyanates.

  本信中，我们通过超瑞利散射（HRS）测量了一系列供体取代的芳香1,3,5-三嗪-2,4,6-三酮的超极化率。对于这些八极非线性光学分子而言，它们的透明度-非线性之间的优异平衡显而易见，这些分子可以通过简单的合成方法从商业异氰酸酯一步步轻松获得。
• Triaryl-1,3,5-triazinane-2,4,6-triones functionalized with electron-rich Fe(ii) and Ru(ii) acetylide complexes: new organometallic octupoles with large hyperpolarizabilities
  作者：Alexander Trujillo、Romain Veillard、Gilles Argouarch、Thierry Roisnel、Anu Singh、Isabelle Ledoux、Frédéric Paul

  DOI：10.1039/c2dt30555k

  日期：——

  and study of a series of trinuclear organometallic triaryl-1,3,5-triazinane-2,4,6-triones functionalized by d6-transition metal acetylides complexes at their periphery are reported. Remarkably large hyperpolarizabilities, far superior to those of related purely organic derivatives, are measured by hyper-Rayleigh scattering (HRS) for these new octupolar chromophores.

  报道了一系列由d 6-过渡金属乙炔配合物官能化的三核有机金属三芳基-1,3,5-三嗪烷-2,4,6-三酮的合成和研究。对于这些新的八极生色团，通过超瑞利散射（HRS）测量了非常大的超极化能力，远远优于相关的纯有机衍生物。
• Synthesis of new luminescent supramolecular assemblies from fluorenyl porphyrins and polypyridyl isocyanurate-based spacers
  作者：Samuel Drouet、Areej Merhi、Gilles Argouarch、Frédéric Paul、Olivier Mongin、Mireille Blanchard-Desce、Christine O. Paul-Roth

  DOI：10.1016/j.tet.2011.10.081

  日期：2012.1

  Two new dendrimeric supramolecular assemblies bearing twelve and twenty-four fluorenyl peripheral donor groups surrounding an organic core have been prepared and studied. These assemblies are composed of three zinc porphyrins possessing each four (ZnTFP) and eight fluorenyl chromophores (ZnOOFP) linked together by a central tris-pyridyl organic ligand. Due to efficient energy transfer between the fluorenyl

  制备并研究了两个新的树枝状超分子组装体，其带有围绕有机核的十二个和二十四个芴基外围供体基团。这些组件由三个锌卟啉组成，每个锌卟啉分别具有四个（ZnTFP）和八个芴基发色团（ZnOOFP），并通过一个中心的三吡啶基有机配体连接在一起。由于在充当天线的芴基臂与充当发射体的Zn中心之间进行了有效的能量转移，这些组件在选择性的紫外线或可见光照射后表现为红色发光体。讨论了这些超分子组装体的动力学稳定性及其对它们的光物理性质的影响。
• Triaryl-1,3,5-triazinane-2,4,6-triones (Isocyanurates) Peripherally Functionalized by Donor Groups: Synthesis and Study of Their Linear and Nonlinear Optical Properties
  作者：Gilles Argouarch、Romain Veillard、Thierry Roisnel、Anissa Amar、Hacène Meghezzi、Abdou Boucekkine、Vincent Hugues、Olivier Mongin、Mireille Blanchard-Desce、Frédéric Paul

  DOI：10.1002/chem.201200484

  日期：2012.9.10

  The linear optical (LO) and nonlinear optical (NLO) properties of a series of isocyanurates functionalized by donor arms at the periphery are reported herein. These octupolar derivatives were obtained in a straightforward way from commercial isocyanate derivatives and were fully characterized. Although several of these compounds are known, those that exhibited the largest NLO activities are all new

  本文报道了在外围通过供体臂官能化的一系列异氰脲酸酯的线性光学（LO）和非线性光学（NLO）性质。这些八极衍生物是直接从商业异氰酸酯衍生物获得的，并已进行了充分表征。尽管这些化合物中的几种是已知的，但显示出最大的NLO活性的化合物都是新化合物。在二阶活性方面，这些衍生物中的几种表现出显着的活性/透明度权衡。就三阶活性而言，较长的衍生物具有较强的供体基团（X = NH 2，NMe 2或NPh 2）被证明具有明显的两光子吸收截面。这些强烈发光的衍生物具有高达410 GM的双光子吸收截面。还进行了DFT计算以阐明其电子结构并合理化其NLO特性。据我们所知，本研究首先涉及这些原始环三聚体的非线性光学性质。
• Triarylisocyanurate‐Based Fluorescent Two‐Photon Absorbers
  作者：Yohan Gautier、Gilles Argouarch、Floriane Malvolti、Benjamin Blondeau、Nicolas Richy、Anissa Amar、Abdou Boucekkine、Krzysztof Nawara、Katarzyna Chlebowicz、Grażyna Orzanowska、Marta Dudek、Katarzyna Matczyszyn、Marek Samoc、Mireille Blanchard‐Desce、Olivier Mongin、Jacek Waluk、Frédéric Paul

  DOI：10.1002/cplu.202000036

  日期：2020.3

  AbstractThe synthesis and characterization of six triarylisocyanurates, featuring 2,7‐fluorenyl or 9,10‐anthracenyl groups incorporated in their peripheral arms are reported. Photophysical studies reveal that these new octupolar derivatives are more fluorescent (ΦF≥0.60 for all new compounds except for 1,3,5‐tri(9H‐fluoren‐2‐yl)‐1,3,5‐triazinane‐2,4,6‐trione 3) and present a red‐shifted lowest absorption and emission compared to their known phenyl analogues of comparable size. Depending on the nature of the terminal substituent, fast intramolecular energy transfer among the three arms or localization of the excitation on a single branch occurs after population of their first singlet excited state. The latter effect was only observed in the presence of strongly electron‐releasing substituents in polar media. These new chromophores are also better two‐photon absorbers than the 1,4‐phenylene‐based isocyanurates reported so far, with cross sections σ2≥500 GM at 770 nm for 4‐NPh2 the fluorenyl group containing (13) and the anthracenyl group containing (14) chromophores. All these spectroscopic features, analyzed with the help of quantum chemical calculations, are crucial for the design of new biphotonic fluorescent dyes.