4-[2-(9-anthryl)]pyridine | 113308-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-[2-(9-anthryl)]pyridine
• 英文别名: 4-(2-(9-anthryl)vinyl)pyridine；4-<2-(9-anthryl)vinyl>pyridine；9-<β-(4-pyridyl)vinyl>anthracene；(E)-4-((2-(anthracen-9-yl)vinyl)pyridine)；trans-9-(4-Pyridylethenyl)anthracene；4-[(E)-2-anthracen-9-ylethenyl]pyridine
• CAS: 113308-40-0
• 化学式: C₂₁H₁₅N
• 分子量: 281.357
• InChiKey: HCWWXYWWSQQPAD-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[2-(9-anthryl)]pyridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到4-<2-(9-anthryl)ethyl>pyridine
  参考文献：
  名称：

  Covalently linked donor-acceptor cyclometalated platinum(II) complexes. Structure and luminescent properties

  摘要：

  Reaction of [Pt(CH3CN)4]2+ with 2,9-diphenyl-1,10-phenanthroline (dpp) in acetonitrile gave the cyclometalated complex [Pt(arc CNN-dpp)(CH3CN)](ClO4) {here abbreviated as [7](ClO4)}, the structure of which has been established by H-1-H-1 COSY and X-ray crystallography: triclinic, P1BAR, a = 13.322(3) angstrom, b = 13.877(3) angstrom, c = 14.164(6) angstrom, alpha = 86.74(3)degrees, lambda = 105.87(3)degrees, gamma = 108.93 (2)degrees, V = 2381.0(12) angstrom3, Z = 2. The resemblance between solution excimeric emission and solid-state emission of 7 suggests that the structure of excimer [7]2* in CH2Cl2 is similar to the dimeric unit in the crystalline state. The coordinated CH3CN in 7 is substitution labile and can be easily replaced by nitrogen bases upon heating in acetone to give covalently-linked donor-acceptor organometallic complexes. Crystal structures of coordinated 4-(4-nitrobenzyl)pyridine and 4-(2-(9-anthryl)vinyl)pyridine substituted complexes (10 and 11, respectively) have been determined: [10](ClO4), triclinic, P1BAR, a = 10.143(2) angstrom, b = 13.025(4) angstrom, c = 13.581(2) angstrom, a = 68.64(2)degrees, beta = 77.15(2)degrees, gamma = 68.00(2)degrees, V = 1541.6(7) angstrom3, Z = 2; [11](ClO4), monoclinic, P2(1)/c, a = 13.065(4) angstrom, b = 18.647(5) angstrom, c = 16.276(4) angstrom, beta = 116.59(2)degrees, V = 3546(3) angstrom3, Z= 4. In both structures, one of the phenyl rings of (arc CNN-dpp) is nearly parallel with the nitrogen base ligand, which is perpendicular to the mean plane defined by the atoms N(1), N(2), C(13), and Pt. The photoluminescent properties of 7 and complexes with covalently linked organic quenchers are described.

  DOI：

  10.1021/ja00077a025
• 作为产物：
  描述：

  9-蒽甲醛 在 哌啶 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 4-[2-(9-anthryl)]pyridine
  参考文献：
  名称：

  Covalently linked donor-acceptor cyclometalated platinum(II) complexes. Structure and luminescent properties

  摘要：

  Reaction of [Pt(CH3CN)4]2+ with 2,9-diphenyl-1,10-phenanthroline (dpp) in acetonitrile gave the cyclometalated complex [Pt(arc CNN-dpp)(CH3CN)](ClO4) {here abbreviated as [7](ClO4)}, the structure of which has been established by H-1-H-1 COSY and X-ray crystallography: triclinic, P1BAR, a = 13.322(3) angstrom, b = 13.877(3) angstrom, c = 14.164(6) angstrom, alpha = 86.74(3)degrees, lambda = 105.87(3)degrees, gamma = 108.93 (2)degrees, V = 2381.0(12) angstrom3, Z = 2. The resemblance between solution excimeric emission and solid-state emission of 7 suggests that the structure of excimer [7]2* in CH2Cl2 is similar to the dimeric unit in the crystalline state. The coordinated CH3CN in 7 is substitution labile and can be easily replaced by nitrogen bases upon heating in acetone to give covalently-linked donor-acceptor organometallic complexes. Crystal structures of coordinated 4-(4-nitrobenzyl)pyridine and 4-(2-(9-anthryl)vinyl)pyridine substituted complexes (10 and 11, respectively) have been determined: [10](ClO4), triclinic, P1BAR, a = 10.143(2) angstrom, b = 13.025(4) angstrom, c = 13.581(2) angstrom, a = 68.64(2)degrees, beta = 77.15(2)degrees, gamma = 68.00(2)degrees, V = 1541.6(7) angstrom3, Z = 2; [11](ClO4), monoclinic, P2(1)/c, a = 13.065(4) angstrom, b = 18.647(5) angstrom, c = 16.276(4) angstrom, beta = 116.59(2)degrees, V = 3546(3) angstrom3, Z= 4. In both structures, one of the phenyl rings of (arc CNN-dpp) is nearly parallel with the nitrogen base ligand, which is perpendicular to the mean plane defined by the atoms N(1), N(2), C(13), and Pt. The photoluminescent properties of 7 and complexes with covalently linked organic quenchers are described.

  DOI：

  10.1021/ja00077a025

文献信息

• Covalently linked anthracene-containing supramolecular complexes of triosmium carbonyl clusters: synthesis, crystal structures and solvatochromic behaviour
  作者：Wai-Yeung Wong、Wing-Tak Wong

  DOI：10.1039/dt9960001853

  日期：——

  Three novel anthracene-containing supramolecules [Os3(µ-H)2(CO)9(µ3-CNC5H4CHCHC14H9)]1, [Os3(µ-H)2(CO)9(µ3-CNC5H4CH2CH2C14H9)]2 and [Os3(µ-H)(CO)10(µ-NC5H3CHCHC14H9)]3(C14H10= anthracene) have been synthesised and the crystal structures of 2 and 3 determined; UV/VIS spectroscopic studies indicated a significant metal–anthracene interaction in the ground state via the conjugated ligand group in 1.

  合成了三种含有蒽的超分子 [Os3(µ-H)2(CO)9(µ3-CNC5H4CHCHC14H9)]1、[Os3(µ-H)2(CO)9(µ3-CNC5H4CH2CH2C14H9)]2 和 [Os3(µ-H)(CO)10(µ-NC5H3CHCHC14H9)]3（C14H10=蒽），并确定了2和3的晶体结构；UV/VIS光谱研究表明，在1的基态中存在显著的金属-蒽相互作用，通过共轭配体基团实现。
• Herstellung konjugierter Polyene mit Anthryl- und<i>N</i>-Methylpyridinium- Endgruppen
  作者：Franz Effenberger、Claus-Peter Niesert

  DOI：10.1055/s-1992-26322

  日期：——

  Preparation of Conjugated Polyenes with Anthryl and N-Methylpyridinium Terminal Groups The synthesis of terminally donor-acceptor substituted polyenes from the respective aldehydes via Horner reactions is described. As donor group the 9-anthryl and as acceptor moiety the 4-(N-methyl)pyridinium residue were chosen. A bicyclo[2.2.2]octane unit was incorporated into the chain to interrupt the conjugation. The separation and characterization of the mixtures of Z/E- isomers obtained in the syntheses was possible.

  制备具有蒽基和 N-甲基吡啶鎓末端基团的共轭多烯 描述了通过霍纳反应从相应的醛中合成末端供体-受体取代的多烯。作为供体基团，选择了 9-蒽基，作为受体分子，选择了 4-（N-甲基）吡啶残基。在链中加入了双环[2.2.2]辛烷单元以中断共轭。合成过程中获得的 Z/E- 异构体混合物的分离和表征成为可能。
• 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications
  作者：Mengjie Liu、Sawaros Onchaiya、Lewis Tan、Mohammad Haghighatbin、Tracey Luu、Tze Owyong、Roozbeh Hushiarian、Conor Hogan、Trevor Smith、Yuning Hong

  DOI：10.3390/molecules22122148

  日期：——

  Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using

  具有聚集诱导发射 (AIE) 特性的荧光染料在聚集时表现出增强的发射。当聚集形成发生时，它们是研究水环境中生物分子和细胞变化的有希望的候选者。在这里，我们报告了一组 9 位官能化的蒽衍生物，它们可以通过钯催化的 Heck 反应方便地合成。使用荧光分析，这些染料被证实在高浓度、粘性溶剂中和溶解性差时形成聚集体时表现出 AIE 行为。然后使用密度泛函理论 (DFT) 计算将它们的光物理特性与其结构特征进一步相关联。最后，我们展示了它们在监测 pH 变化、定量球状蛋白质、
• Synthesis and spectral luminescent properties of certain pyridine and quinoline analogs of isomeric distyrylnaphthalenes and styryl- and distyrylanthracenes
  作者：E. M. Vernigor、M. V. Koz'menko、S. A. Lebedev、E. A. Luk'yanets、L. P. Savvina、V. K. Shalaev

  DOI：10.1007/bf00486918

  日期：1987.6
• VERNIGOR, E. M.;KOZMENKO, M. V.;LEBEDEV, S. A.;LUKYANETS, E. A.;SAVVINA, +, XIMIYA GETEROTSIKL. SOED.,(1987) N 6, 820-823
  作者：VERNIGOR, E. M.、KOZMENKO, M. V.、LEBEDEV, S. A.、LUKYANETS, E. A.、SAVVINA, +

  DOI：——

  日期：——