N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[(trimethylsilyl)ethynyl]aniline | 834856-13-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[(trimethylsilyl)ethynyl]aniline
• 英文别名: N,N-dibutyl-4-(2-trimethylsilylethynyl)-3-[2-tri(propan-2-yl)silylethynyl]aniline
• CAS: 834856-13-2
• 化学式: C₃₀H₅₁NSi₂
• 分子量: 481.913
• InChiKey: FLVATWPCRDMXEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[(trimethylsilyl)ethynyl]aniline 在 吡啶 、 氢氧化钾 、 copper(l) iodide 、 copper diacetate 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 76.5h， 生成 7-N,7-N,16-N,16-N-tetrabutyl-24-azatetracyclo[20.3.1.04,9.014,19]hexacosa-1(26),4(9),5,7,14(19),15,17,22,24-nonaen-2,10,12,20-tetrayne-7,16-diamine
  参考文献：
  名称：

  Dynamic Proton-Induced Emission Switching in Donor-Functionalized Dehydrobenzopyrid[15]annulenes

  摘要：

  An isomeric pair of 15-membered dehydrobenzopyridannulenes functionalized with -NBu2 groups as pi-electron donors was prepared and their steady-state spectroscopic parameters investigated. The property differences arising from placement of the pyridine nitrogen relative to the macrocycle, as well as the differential effects of stepwise protonation of the acceptor and donor nitrogens, were examined. The macrocycles exhibited dynamic shifting in the emission spectra, which is believed to correlate to induced changes in the frontier molecular orbitals of the molecules.

  DOI：

  10.1021/jo070827c
• 作为产物：
  描述：

  N,N-dibutyl-4-iodo-3-[(triisopropylsilyl)ethynyl]aniline 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以97%的产率得到N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[(trimethylsilyl)ethynyl]aniline
  参考文献：
  名称：

  Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes

  摘要：

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.

  DOI：

  10.1021/ja044175a

文献信息

• Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
  作者：Jeremiah A. Marsden、Jeremie J. Miller、Laura D. Shirtcliff、Michael M. Haley

  DOI：10.1021/ja044175a

  日期：2005.3.1

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.
• Dynamic Proton-Induced Emission Switching in Donor-Functionalized Dehydrobenzopyrid[15]annulenes
  作者：Eric L. Spitler、Sean P. McClintock、Michael M. Haley

  DOI：10.1021/jo070827c

  日期：2007.8.31

  An isomeric pair of 15-membered dehydrobenzopyridannulenes functionalized with -NBu2 groups as pi-electron donors was prepared and their steady-state spectroscopic parameters investigated. The property differences arising from placement of the pyridine nitrogen relative to the macrocycle, as well as the differential effects of stepwise protonation of the acceptor and donor nitrogens, were examined. The macrocycles exhibited dynamic shifting in the emission spectra, which is believed to correlate to induced changes in the frontier molecular orbitals of the molecules.