1,4-diethyl-2-(phenylethynyl)-5-(trimethylsilylethynyl)-benzene | 1094159-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-diethyl-2-(phenylethynyl)-5-(trimethylsilylethynyl)-benzene
• 英文别名: 2-[2,5-Diethyl-4-(2-phenylethynyl)phenyl]ethynyl-trimethylsilane；2-[2,5-diethyl-4-(2-phenylethynyl)phenyl]ethynyl-trimethylsilane
• CAS: 1094159-78-0
• 化学式: C₂₃H₂₆Si
• 分子量: 330.545
• InChiKey: YDUBVIBNINXINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-diethyl-2-(phenylethynyl)-5-(trimethylsilylethynyl)-benzene 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Upon the intrinsic optical properties of oligo(p-phenyleneethynylene)s (OPEs). Synthesis of OPE3 for experimental gas-phase absorption studies

  摘要：

  A new oligo(p-phenyleneethynylene) (OPE3) was synthesized by step-wise Pd-catalyzed cross-coupling reactions. The molecule incorporates an amine functionality, which allows for transfer of the protonated molecule to the gas phase by electrospray ionization leaving the OPE entity neutral. This method has allowed for the first experimental gas-phase absorption spectrum of an OPE3 by action spectroscopy, employing an electrostatic ion storage ring in combination with a laser system. The studies reveal the effect of having a positive charge in proximity to the Conjugated backbone of OPE3 in the absence of any interfering solvent molecules. In addition, ionization energies and electron affinities of OPE2-OPE17 were Calculated at the density functional theory (DFT) level. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.068
• 作为产物：
  描述：

  苯乙炔 、 (2,5-diethyl-4-iodophenylethynyl)trimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到1,4-diethyl-2-(phenylethynyl)-5-(trimethylsilylethynyl)-benzene
  参考文献：
  名称：

  Upon the intrinsic optical properties of oligo(p-phenyleneethynylene)s (OPEs). Synthesis of OPE3 for experimental gas-phase absorption studies

  摘要：

  A new oligo(p-phenyleneethynylene) (OPE3) was synthesized by step-wise Pd-catalyzed cross-coupling reactions. The molecule incorporates an amine functionality, which allows for transfer of the protonated molecule to the gas phase by electrospray ionization leaving the OPE entity neutral. This method has allowed for the first experimental gas-phase absorption spectrum of an OPE3 by action spectroscopy, employing an electrostatic ion storage ring in combination with a laser system. The studies reveal the effect of having a positive charge in proximity to the Conjugated backbone of OPE3 in the absence of any interfering solvent molecules. In addition, ionization energies and electron affinities of OPE2-OPE17 were Calculated at the density functional theory (DFT) level. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.068

文献信息

• Synthesis and spectroscopic study of phenylene–(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems
  作者：Jing-Kun Fang、De-Lie An、Kan Wakamatsu、Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Shin-ichi Akita、Daisuke Matsuo、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2010.05.016

  日期：2010.7

  To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic pi-systems, phenylene-(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of beta-substituted sulfones. These substituted phenyleneethynylenes showed large molar absorption coefficients epsilon, and emitted strong fluorescence upon UV light irradiation. Phenylene (poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields Phi(F) as their polyethynylene motifs -(C C)(n)- expanded. The drastic decrease of fluorescence quantum yields Phi(F) were explained in terms of increasing nonradiative reaction rate constants k(nr), which had been determined by the corresponding fluorescence quantum yields Phi(F) and lifetime values tau. The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state. Comparison of slope values rho in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylene (poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic pi-systems with cyano group did little. (C) 2010 Elsevier Ltd. All rights reserved.
• Upon the intrinsic optical properties of oligo(p-phenyleneethynylene)s (OPEs). Synthesis of OPE3 for experimental gas-phase absorption studies
  作者：Torben Ryhding、Maj-Britt Suhr Kirketerp、Umesh Kadhane、Morten Køcks Lykkegaard、Subhasis Panja、Steen Brøndsted Nielsen、Mogens Brøndsted Nielsen

  DOI：10.1016/j.tet.2008.08.068

  日期：2008.12

  A new oligo(p-phenyleneethynylene) (OPE3) was synthesized by step-wise Pd-catalyzed cross-coupling reactions. The molecule incorporates an amine functionality, which allows for transfer of the protonated molecule to the gas phase by electrospray ionization leaving the OPE entity neutral. This method has allowed for the first experimental gas-phase absorption spectrum of an OPE3 by action spectroscopy, employing an electrostatic ion storage ring in combination with a laser system. The studies reveal the effect of having a positive charge in proximity to the Conjugated backbone of OPE3 in the absence of any interfering solvent molecules. In addition, ionization energies and electron affinities of OPE2-OPE17 were Calculated at the density functional theory (DFT) level. (C) 2008 Elsevier Ltd. All rights reserved.