1,4-bis-{2-[-(2-iodoethoxy)ethoxy]ethoxy}benzene | 944031-49-6

• 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-iodoethoxy)ethoxy]ethoxy}benzene
• CAS: 944031-49-6
• 化学式: C₁₈H₂₈I₂O₆
• 分子量: 594.226
• InChiKey: SMZXXJMDWJULHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  26.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4,4'-联吡啶 、 1,4-bis-{2-[-(2-iodoethoxy)ethoxy]ethoxy}benzene 在 ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以19%的产率得到
  参考文献：
  名称：

  Dynamics of Charge Transfer and Recombination in a Covalently-Linked, Face-to-Face Electron Donor-Acceptor Complex

  摘要：

  The photophysical properties of a covalently-linked, electron donor-acceptor (EDA) complex, containing 1,4-dialkoxybenzene and N,N'-dialkyl-4,4'-bipyridinium dication subunits, have been studied in polar solvents. The structure of the compound has been elucidated by X-ray crystallography, 2D NMR, and resonance Raman spectroscopy. Excitation of the ground-state EDA complex with a short laser pulse results in formation of the corresponding excited charge-transfer state, which is weakly fluorescent. The excited state decays, at least in part, via charge transfer to form an intimate radical ion pair (RIP) within a few picoseconds. The free energy content of the RIP decreases with increasing polarity of the solvent, and there is a concomitant increase in the rate of charge recombination, which also occurs on the picosecond time scale. For this system, the dynamics for deactivation of the RIP can be described satisfactorily in terms of both conventional nonadiabatic electron-transfer theory and an exponential energy gap law.

  DOI：

  10.1021/ja00104a037
• 作为产物：
  描述：

  1,4-bis(tosylate ethyloxy ethyloxy ethyl)benzene 在 sodium iodide 作用下， 生成 1,4-bis-{2-[-(2-iodoethoxy)ethoxy]ethoxy}benzene
  参考文献：
  名称：

  Dynamics of Charge Transfer and Recombination in a Covalently-Linked, Face-to-Face Electron Donor-Acceptor Complex

  摘要：

  The photophysical properties of a covalently-linked, electron donor-acceptor (EDA) complex, containing 1,4-dialkoxybenzene and N,N'-dialkyl-4,4'-bipyridinium dication subunits, have been studied in polar solvents. The structure of the compound has been elucidated by X-ray crystallography, 2D NMR, and resonance Raman spectroscopy. Excitation of the ground-state EDA complex with a short laser pulse results in formation of the corresponding excited charge-transfer state, which is weakly fluorescent. The excited state decays, at least in part, via charge transfer to form an intimate radical ion pair (RIP) within a few picoseconds. The free energy content of the RIP decreases with increasing polarity of the solvent, and there is a concomitant increase in the rate of charge recombination, which also occurs on the picosecond time scale. For this system, the dynamics for deactivation of the RIP can be described satisfactorily in terms of both conventional nonadiabatic electron-transfer theory and an exponential energy gap law.

  DOI：

  10.1021/ja00104a037

文献信息

• Two Classes of Alongside Charge-Transfer Interactions Defined in One [2]Catenane
  作者：Sune Nygaard、Stinne W. Hansen、John C. Huffman、Frank Jensen、Amar H. Flood、Jan O. Jeppesen

  DOI：10.1021/ja069047w

  日期：2007.6.13

  A [2]catenane, which incorporates hydroquinone (HQ) and a sterically bulky tetrathiafulvalene (TTF) into a bismacrocycle, has been designed to probe the alongside charge-transfer (CT) interactions taking place between a TTF unit and one of the bipyridinium moieties in the tetracationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)). A template-directed strategy employs the HQ unit as the primary template for formation of the tetracationic cyclophane CBPQT(4+), affording the desired [2]catenane structure but as an uncharacteristic green solid. The X-ray crystal structure and detailed C-13 NMR assignments have identified a stereoselective preference for catenation about the cis isomer. The H-1 NMR spectroscopy, electrochemistry, and X-ray crystallography all confirm that the CBPQT(4+) cyclophane encircles the HQ unit, thereby defining a structure which would normally determine a red color. The visible-NIR region of the absorption spectrum displays a band at similar to 740 nm that is unambiguously assigned to a TTF -> CBPQT(4+) CT transition on the basis of resonance Raman spectroscopy using 785 nm excitation. The profile of the CT band changes depending on the ratio of the cis- to trans-TTF isomers in the [2]catenane for which the molar absorptivity of each isomer is estimated to be significantly different at epsilon(max) = 380 and 3690 M-1 cm(-1), respectively. Molecular modeling studies confirmed that the observed difference in the absorp-tion spectroscopic profile can be accounted for by both a better overlap of the HOMO(TTF) and LUMO+1(CBPQT(4+)) as well as a more stable face-to-face (pi center dot center dot center dot pi) conformation in the trans isomer compared to the edge-to-face cis isomer of the [2]catenane. The latter is arranged for pi-orbital overlap through the sulfur atoms of the TTF unit, thereby defining an [S pi center dot center dot center dot pi] interaction.