2-(pyrene-1-carboxamido)terephthalic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(pyrene-1-carboxamido)terephthalic acid
• 英文别名: 2-(Pyrene-1-carbonylamino)terephthalic acid；2-(pyrene-1-carbonylamino)terephthalic acid
• 化学式: C₂₅H₁₅NO₅
• 分子量: 409.398
• InChiKey: GOZVKGAHNVDKQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) nitrate 、 2-(pyrene-1-carboxamido)terephthalic acid 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以65%的产率得到
  参考文献：
  名称：

  Dual Changes in Conformation and Optical Properties of Fluorophores within a Metal–Organic Framework during Framework Construction and Associated Sensing Event

  摘要：

  Microsized chemosensor particle (CPP-16, CPP means coordination polymer particle), which is made from a metal-organic framework (MOF), is synthesized using pyrene-functionalized organic building block. This building block contains three important parts, a framework construction part, a Cu(2+) detection part, and a fluorophore part. PXRD studies have revealed that CPP-16 has a 3D cubic structure of MOF-5. During both MOF formation and sensing event, fluorophores within CPP-16 undergo dual changes in conformation and optical properties. After MOF construction, pyrene moieties experience an unusual complete conversion from monomer to excimer form. This conversion takes place due to a confinement effect induced by space limitations within the MOF structure. The selective sensing ability of CPP-16 on Cu(2+) over many other metal ions is verified by emission spectra and is also visually identified by fluorescence microscopy images. Specific interaction of Cu(2+) with binding sites within CPP-16 causes a second conformational change of the fluorophores, where they change from stacked excimer (CPP-16) to quenched excimer states (CPP-16·Cu(2+)).

  DOI：

  10.1021/ja504204d
• 作为产物：
  描述：

  1-芘甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-(pyrene-1-carboxamido)terephthalic acid
  参考文献：
  名称：

  Dual Changes in Conformation and Optical Properties of Fluorophores within a Metal–Organic Framework during Framework Construction and Associated Sensing Event

  摘要：

  Microsized chemosensor particle (CPP-16, CPP means coordination polymer particle), which is made from a metal-organic framework (MOF), is synthesized using pyrene-functionalized organic building block. This building block contains three important parts, a framework construction part, a Cu(2+) detection part, and a fluorophore part. PXRD studies have revealed that CPP-16 has a 3D cubic structure of MOF-5. During both MOF formation and sensing event, fluorophores within CPP-16 undergo dual changes in conformation and optical properties. After MOF construction, pyrene moieties experience an unusual complete conversion from monomer to excimer form. This conversion takes place due to a confinement effect induced by space limitations within the MOF structure. The selective sensing ability of CPP-16 on Cu(2+) over many other metal ions is verified by emission spectra and is also visually identified by fluorescence microscopy images. Specific interaction of Cu(2+) with binding sites within CPP-16 causes a second conformational change of the fluorophores, where they change from stacked excimer (CPP-16) to quenched excimer states (CPP-16·Cu(2+)).

  DOI：

  10.1021/ja504204d

文献信息

• Dual Changes in Conformation and Optical Properties of Fluorophores within a Metal–Organic Framework during Framework Construction and Associated Sensing Event
  作者：Won Cho、Hee Jung Lee、Goeun Choi、Sora Choi、Moonhyun Oh

  DOI：10.1021/ja504204d

  日期：2014.9.3

  Microsized chemosensor particle (CPP-16, CPP means coordination polymer particle), which is made from a metal-organic framework (MOF), is synthesized using pyrene-functionalized organic building block. This building block contains three important parts, a framework construction part, a Cu(2+) detection part, and a fluorophore part. PXRD studies have revealed that CPP-16 has a 3D cubic structure of MOF-5. During both MOF formation and sensing event, fluorophores within CPP-16 undergo dual changes in conformation and optical properties. After MOF construction, pyrene moieties experience an unusual complete conversion from monomer to excimer form. This conversion takes place due to a confinement effect induced by space limitations within the MOF structure. The selective sensing ability of CPP-16 on Cu(2+) over many other metal ions is verified by emission spectra and is also visually identified by fluorescence microscopy images. Specific interaction of Cu(2+) with binding sites within CPP-16 causes a second conformational change of the fluorophores, where they change from stacked excimer (CPP-16) to quenched excimer states (CPP-16·Cu(2+)).