N-((3-dioxoisoindolin-2yl)propyl)pyrene-1-carboxamide | 1214753-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-((3-dioxoisoindolin-2yl)propyl)pyrene-1-carboxamide
• 英文别名: PyA-PI；N-[3-(1,3-dioxoisoindol-2-yl)propyl]pyrene-1-carboxamide
• CAS: 1214753-35-1
• 化学式: C₂₈H₂₀N₂O₃
• 分子量: 432.478
• InChiKey: XNMMEZRZNPXZEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-氨基丙基)苯二甲酰亚胺 、 pyren-1-ylcarbonyl chloride 生成 N-((3-dioxoisoindolin-2yl)propyl)pyrene-1-carboxamide
  参考文献：
  名称：

  Dynamics and Efficiency of Electron Injection and Transport in DNA Using Pyrenecarboxamide as an Electron Donor and 5-Bromouracil as an Electron Acceptor

  摘要：

  The photophysical and photochemical behavior of a series of hairpin-forming DNA conjugates possessing a 5'-tethered pyrenecarboxamide chromophore and one or two bromouracil bases has been investigated Quenching of the pyrene fluorescence and transient absorption spectra characteristic of the pyrene cation radical are observed only when bromouracil is located at the first or second base pair position nearest to the point of pyrene attachment These observations are consistent with an intercalated structure for these conjugates in which pyrene is adjacent to the second base pair Selective quenching of singlet pyrene by bromouracil but not by thymine is consistent with the free energy for charge separation estimated using Weller s equation Low quantum yields for loss of bromide when bromouracil is not adjacent to pyrene are attributed to inefficient charge separation via either a multistep electron transport or a single-step superexchange mechanism Quantum yields are only weakly dependent upon the distance between pyrene and bromouracil as expected for a multistep electron transport mechanism Loss of bromide from conjugates possessing two bromouracils occurs sequentially For adjacent bromouracils competitive loss of bromide from both bromouracils is observed whereas for nonadjacent bromouracils loss of bromide from the proximal bromouracil occurs prior to any loss from the distal bromouracil consistent with a slower rate constant for electron transport vs loss of bromide

  DOI：

  10.1021/jp9107393

文献信息

• Dynamics and Efficiency of Electron Injection and Transport in DNA Using Pyrenecarboxamide as an Electron Donor and 5-Bromouracil as an Electron Acceptor
  作者：Pierre Daublain、Arun K. Thazhathveetil、Vladimir Shafirovich、Qiang Wang、Anton Trifonov、Torsten Fiebig、Frederick D. Lewis

  DOI：10.1021/jp9107393

  日期：2010.11.18

  The photophysical and photochemical behavior of a series of hairpin-forming DNA conjugates possessing a 5'-tethered pyrenecarboxamide chromophore and one or two bromouracil bases has been investigated Quenching of the pyrene fluorescence and transient absorption spectra characteristic of the pyrene cation radical are observed only when bromouracil is located at the first or second base pair position nearest to the point of pyrene attachment These observations are consistent with an intercalated structure for these conjugates in which pyrene is adjacent to the second base pair Selective quenching of singlet pyrene by bromouracil but not by thymine is consistent with the free energy for charge separation estimated using Weller s equation Low quantum yields for loss of bromide when bromouracil is not adjacent to pyrene are attributed to inefficient charge separation via either a multistep electron transport or a single-step superexchange mechanism Quantum yields are only weakly dependent upon the distance between pyrene and bromouracil as expected for a multistep electron transport mechanism Loss of bromide from conjugates possessing two bromouracils occurs sequentially For adjacent bromouracils competitive loss of bromide from both bromouracils is observed whereas for nonadjacent bromouracils loss of bromide from the proximal bromouracil occurs prior to any loss from the distal bromouracil consistent with a slower rate constant for electron transport vs loss of bromide