2,3-naphtho-aza-crown-5 | 420827-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-naphtho-aza-crown-5
• 英文别名: 2,5,11,14-Tetraoxa-8-azatricyclo[13.8.0.017,22]tricosa-1(23),15,17,19,21-pentaene；2,5,11,14-tetraoxa-8-azatricyclo[13.8.0.017,22]tricosa-1(23),15,17,19,21-pentaene
• CAS: 420827-31-2
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: GJAYCIIIBPRBAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-naphtho-aza-crown-5 、 N-[(chloromethyl)carbonyl]-1-pyrenemethylamine 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以73%的产率得到N-(pyrenylmethyl)naphtho-azacrown-5
  参考文献：
  名称：

  FRET-derived ratiometric fluorescence sensor for Cu2+

  摘要：

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.063
• 作为产物：
  描述：

  2,3-naphtho-azacrown-5-p-toluenesulfonate 在 disodium hydrogenphosphate 、 sodium 作用下， 生成 2,3-naphtho-aza-crown-5
  参考文献：
  名称：

  FRET-derived ratiometric fluorescence sensor for Cu2+

  摘要：

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.063

文献信息

• FRET-derived ratiometric fluorescence sensor for Cu2+
  作者：Hyun Jung Kim、Sun Young Park、Sangwoon Yoon、Jong Seung Kim

  DOI：10.1016/j.tet.2007.11.063

  日期：2008.2

  New N-(pyrenylmethyl)naphtho-azacrown-5 (1) was synthesized as an 'On-Off' fluorescent chemosensor for Cu2+. Excited at 240 nm corresponding to the absorption of naphthalene unit (energy donor) of 1, emission at 380 nm from pyrene unit (energy acceptor) is observed, indicating that intramolecular fluorescence resonance energy transfer (FRET-On) occurs in 1. When Cu2+ is added to a solution of 1, however, the fluorescence of pyrene is strongly quenched (FRET-Off) whereas that of naphthalene group is revived. Such FRET 'On-Off' behavior of 1 is observed only in the case of Cu2+ binding, but not for other metal cations. The high selectivity of 1 toward Cu2+ can be potentially applied to a new kind of FRET-based chemosensor. The FRET On-Off behavior is supported by computational studies. The calculated molecular orbitals of HOMO and LUMOs suggest the excited-state interactions leading to FRET from naphthalene to pyrene in 1, but no electron density changes in 1.Cu2+ complex. (c) 2007 Elsevier Ltd. All rights reserved.