1,4-bis(2-(2,5-dibutoxy-4-ethynylphenyl)ethynyl)-2,5-dibutoxybezene | 1188511-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(2-(2,5-dibutoxy-4-ethynylphenyl)ethynyl)-2,5-dibutoxybezene
• CAS: 1188511-10-5
• 化学式: C₅₀H₆₂O₆
• 分子量: 759.039
• InChiKey: YFNQXZBJRLPYBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  56.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(2-(2,5-dibutoxy-4-ethynylphenyl)ethynyl)-2,5-dibutoxybezene 、 1,3-bis((trimethylsilyl)oxy)-2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3-imidazolidine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以17%的产率得到1,4-bis(2-(2,5-dibutoxy-4-(2-(4-(4,4,5,5-tetramethyl-1,3-bis-((trimethylsilyl)oxy)imidazolidin-2-yl)phenyl)ethynyl)phenyl)-ethynyl)-2,5-dibutoxybenzene
  参考文献：
  名称：

  Evaluation of the β Value of the Phenylene Ethynylene Unit by Probing the Exchange Interaction between Two Nitronyl Nitroxides

  摘要：

  A series of nitronyl nitroxide radicals having different lengths of phenylene ethynylene molecular wire were synthesized to investigate the decay constant of p-phenylene ethynylene. By the measurement and simulation of the ESR spectra of the biradicals, it was found that the exchange interaction decreased with a decay constant (beta) of 039 angstrom(-1) as the length of the molecule increased. This result indicates that the spin-spin exchange interaction between neutral radicals has a decay constant similar to that of the molecular conductance. This value of the decay constant indicates that a hopping mechanism does not take place in the measurement of the exchange interaction between neutral radicals even when the molecular wire has enough length to show hopping conduction of electrons.

  DOI：

  10.1021/jo4015062
• 作为产物：
  描述：

  1,4-二丁氧基-2-碘-5-(2-(三甲基甲硅烷基)乙炔基)苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,4-bis(2-(2,5-dibutoxy-4-ethynylphenyl)ethynyl)-2,5-dibutoxybezene
  参考文献：
  名称：

  Evaluation of the β Value of the Phenylene Ethynylene Unit by Probing the Exchange Interaction between Two Nitronyl Nitroxides

  摘要：

  A series of nitronyl nitroxide radicals having different lengths of phenylene ethynylene molecular wire were synthesized to investigate the decay constant of p-phenylene ethynylene. By the measurement and simulation of the ESR spectra of the biradicals, it was found that the exchange interaction decreased with a decay constant (beta) of 039 angstrom(-1) as the length of the molecule increased. This result indicates that the spin-spin exchange interaction between neutral radicals has a decay constant similar to that of the molecular conductance. This value of the decay constant indicates that a hopping mechanism does not take place in the measurement of the exchange interaction between neutral radicals even when the molecular wire has enough length to show hopping conduction of electrons.

  DOI：

  10.1021/jo4015062

文献信息

• Length Dependence for Intramolecular Energy Transfer in Three- and Four-Color Donor−Spacer−Acceptor Arrays
  作者：Anthony Harriman、Laura J. Mallon、Kristopher J. Elliot、Alexandre Haefele、Gilles Ulrich、Raymond Ziessel

  DOI：10.1021/ja9038856

  日期：2009.9.23

  A series of donor-spacer-acceptor triads has been synthesized and fully characterized. Both donor and acceptor units are built from boron dipyrromethene (BODIPY) dyes but they differ in their respective conjugation lengths, and thereby offer quite disparate optical properties. The spacer units comprise an oligomer of 1,4-phenylene-diethynylene repeat units and allow the boron-boron separation distance to be varied progressively from 18 to 38 angstrom. A notable feature of this series is that each subunit can be selectively excited with monochromatic light. Highly efficacious electronic energy transfer (EET) occurs from the first-excited singlet state localized on the conventional BODIPY dye to its counterpart resident on the expanded BODIPY-based nucleus, but the rate constant follows a nonlinear evolution with separation distance. Overall, the rate of EET falls by only a factor of 4-fold on moving from the shortest to the longest spacer. This shallow length dependence is a consequence of the energy gap between donor and spacer units becoming smaller as the molecular length increases. Interestingly, a simple relationship exists between the measured electronic resistance of the spacer unit and the Huang-Rhys factor determined by emission spectroscopy. Both parameters relate to the effective conjugation length. Direct illumination of the spacer unit leads to EET to both terminals, followed by EET from conventional BODIPY to the expanded version. In each case, EET to the expanded dye involves initial population of the second-singlet excited state, whereas transfer from spacer to the conventional BODIPY dye populates the S-2 state for shorter lengths but the S, state for the longer analogues. The rate of EET from spacer to conventional BODIPY dye, as measured for the corresponding molecular dyads, is extremely fast,(>10(11) s(-1)) and scales with the spectral overlap integral. The relative partitioning of EET from the spacer to each terminal is somewhat sensitive to the molecular length, with the propensity to populate the conventional BODIPY dye changing from 65% for N = 0 to 45% for N = 2. The most likely explanation for this behavior can be traced to the disparate spectral overlap integrals for the two dyes. These systems have been complemented by a molecular tetrad in which pyrene residues replace the fluorine atoms present on the conventional BODIPY-based dye. Here, rapid EET occurs from pyrene to the BODIPY dye and is followed by slower, long-range EET to the opposite terminal. Such materials are seen as highly attractive solar concentrators when dispersed in transparent plastic media and used under conditions where both inter- and intramolecular EET operate.