1,4-diiodo-2,5-bis[(E)-2-(4-propan-2-ylphenyl)ethenyl]benzene | 851345-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,4-diiodo-2,5-bis[(E)-2-(4-propan-2-ylphenyl)ethenyl]benzene
• CAS: 851345-56-7
• 化学式: C₂₈H₂₈I₂
• 分子量: 618.339
• InChiKey: PHRSYSLBRZZMIQ-KAVGSWPWSA-N

物化性质

• 沸点：
  605.4±55.0 °C(Predicted)
• 密度：
  1.545±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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-diiodo-2,5-bis[(E)-2-(4-propan-2-ylphenyl)ethenyl]benzene 、 4-乙炔基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到4-[2-[2,5-bis[(E)-2-(4-propan-2-ylphenyl)ethenyl]-4-(2-pyridin-4-ylethynyl)phenyl]ethynyl]pyridine
  参考文献：
  名称：

  Switching of Intramolecular Charge Transfer in Cruciforms:  Metal Ion Sensing

  摘要：

  Three different cruciforms containing the 1,4-bis-4'-pyridylethynyl-2,5-distyrylbenzene or the 1,4-bis-phenylethynyl-2,5-distyrylbenzene unit were synthesized and investigated with respect to their metal sensing properties. Upon addition of metal cations to these cruciforms, either a bathochromic or hypsochromic shift in emission and absorption is observed. The shift depends on whether the metal coordinates preferentially to the pyridine or to the dibutylaniline branches of the cruciforms. The three cruciforms were exposed to a selection of metal cations in dichloromethane, and their emission was examined. The cruciforms show differential sensing of metal cations, that is, different metals can be specifically discerned upon exposure to three cruciforms but not when exposed to only one. The system can discern calcium from magnesium cations and silver from mercury or lithium cations.

  DOI：

  10.1021/ja050017n
• 作为产物：
  描述：

  1,4-双(溴甲基)-2,5-二碘苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,4-diiodo-2,5-bis[(E)-2-(4-propan-2-ylphenyl)ethenyl]benzene
  参考文献：
  名称：

  Cruciforms as Functional Fluorophores:  Response to Protons and Selected Metal Ions

  摘要：

  The photophysics of dialkylamino- and/or pyridine-containing functional chromophores, 1,4-distyryl-2,5-bis(ethynylaryl) benzenes (cruciforms) was investigated; their fluorescence quantum yields and emissive lifetimes were determined. Depending upon their substituents, the frontier molecular orbitals (FMOs) of these cruciforms are either congruent, i.e., HOMO and LUMO occupy the same real space, or disjoint, i.e., the HOMO is located on one branch of the cruciform while the LUMO is located on the second one. Donor-acceptor substitution leads to a disjoint FMO pattern, while the parent 1,4-distyryl-2,5-bis(phenylethynyl)benzene shows congruent FMOs. The photophysics of the cruciforms was investigated upon addition of either an excess of trifluoroacetic acid or an excess of selected metal (Mg2+, Ca2+, Mn2+, Zn2+) trifluoromethanesulfonate salts. Addition of either metal ions or protons led to analogous but not identical changes in the spectroscopic properties of the investigated cruciforms. The collected data suggest that the metals bind preferentially at the aniline nitrogen and not at the electron-rich arene. The spatially separated FMOs permit the independent manipulation of the HOMO and the LUMO of such cruciforms. If the branches contain metal-complexing moieties, metal binding leads to either a hypsochromic or a bathochromic shift in emission via interaction of the metal cations with either the HOMO or the LUMO.

  DOI：

  10.1021/ja061112e

文献信息

• Terpyridine-Based Cruciform−Zn²⁺ Complexes as Anion-Responsive Fluorophores
  作者：Scott M. Brombosz、Anthony J. Zucchero、Ronnie L. Phillips、Diana Vazquez、Alando Wilson、Uwe H. F. Bunz

  DOI：10.1021/ol7020302

  日期：2007.10.1

  [GRAPHICS]The synthesis of a terpyridine-appended, zinc-complexed cruciform, 3-Zn2+, and the anion-reactive modulation of its emissive properties in acetone-water mixtures are reported.
• Cruciforms as Functional Fluorophores:  Response to Protons and Selected Metal Ions
  作者：Anthony J. Zucchero、James N. Wilson、Uwe H. F. Bunz

  DOI：10.1021/ja061112e

  日期：2006.9.1

  The photophysics of dialkylamino- and/or pyridine-containing functional chromophores, 1,4-distyryl-2,5-bis(ethynylaryl) benzenes (cruciforms) was investigated; their fluorescence quantum yields and emissive lifetimes were determined. Depending upon their substituents, the frontier molecular orbitals (FMOs) of these cruciforms are either congruent, i.e., HOMO and LUMO occupy the same real space, or disjoint, i.e., the HOMO is located on one branch of the cruciform while the LUMO is located on the second one. Donor-acceptor substitution leads to a disjoint FMO pattern, while the parent 1,4-distyryl-2,5-bis(phenylethynyl)benzene shows congruent FMOs. The photophysics of the cruciforms was investigated upon addition of either an excess of trifluoroacetic acid or an excess of selected metal (Mg2+, Ca2+, Mn2+, Zn2+) trifluoromethanesulfonate salts. Addition of either metal ions or protons led to analogous but not identical changes in the spectroscopic properties of the investigated cruciforms. The collected data suggest that the metals bind preferentially at the aniline nitrogen and not at the electron-rich arene. The spatially separated FMOs permit the independent manipulation of the HOMO and the LUMO of such cruciforms. If the branches contain metal-complexing moieties, metal binding leads to either a hypsochromic or a bathochromic shift in emission via interaction of the metal cations with either the HOMO or the LUMO.
• Switching of Intramolecular Charge Transfer in Cruciforms:  Metal Ion Sensing
  作者：James N. Wilson、Uwe H. F. Bunz

  DOI：10.1021/ja050017n

  日期：2005.3.1

  Three different cruciforms containing the 1,4-bis-4'-pyridylethynyl-2,5-distyrylbenzene or the 1,4-bis-phenylethynyl-2,5-distyrylbenzene unit were synthesized and investigated with respect to their metal sensing properties. Upon addition of metal cations to these cruciforms, either a bathochromic or hypsochromic shift in emission and absorption is observed. The shift depends on whether the metal coordinates preferentially to the pyridine or to the dibutylaniline branches of the cruciforms. The three cruciforms were exposed to a selection of metal cations in dichloromethane, and their emission was examined. The cruciforms show differential sensing of metal cations, that is, different metals can be specifically discerned upon exposure to three cruciforms but not when exposed to only one. The system can discern calcium from magnesium cations and silver from mercury or lithium cations.