1,2-di(2-methoxyl)benzoylbenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-di(2-methoxyl)benzoylbenzene
• 英文别名: Bis(2-methoxybenzoyl)-benzene；[2-(2-methoxybenzoyl)phenyl]-(2-methoxyphenyl)methanone
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: YFAOEKJASCECML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-di(2-methoxyl)benzoylbenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到di(2-hydroxyl)benzoylbenzene
  参考文献：
  名称：

  Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

  摘要：

  Multifunction luminogens have emerged as promising candidates in high-performance sensor and imaging systems. Concise approaches to the synthesis of such molecules are urgently required both for fundamental research and technological applications. In this study, a new symmetric ligand of di(2-hydroxyphenyl)phthalazine with multiple binding sites around a phthalazine unit was readily synthesized, which could be converted efficiently into an asymmetric luminogen (OBNDHPP) through the formation of oxygen-boron-nitrogen bonding. This molecule has a twistable it-extended backbone with a tetracoordinated boron core bearing two bulky phenyl groups, giving it abundant optical properties including a large Stokes shift piezochromism and aggregationinduced emission enhancement. Importantly, the presence of a free phenolic hydroxyl group in the backbone of OBN-DHPP enables the incorporation of various functional moieties into the asymmetric luminogen. As an example, polyethylene glycol (PEG)-modified luminogen (OBN-DHPP-PEG(45)) was synthesized. In the aqueous medium, OBN-DHPP-PEG(45) could self-assemble into spherical nanoparticles with low cytotoxicity and excellent emission performance as well as high solubility. The results of flow cytometry and fluorescence microscopy reveal that these nanoparticles could be internalized successfully by HeLa cells, demonstrating their potential application in bioimaging.

  DOI：

  10.1021/acs.joc.8b01340
• 作为产物：
  描述：

  邻苯二甲酰氯 在 碘 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 生成 1,2-di(2-methoxyl)benzoylbenzene
  参考文献：
  名称：

  Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

  摘要：

  Multifunction luminogens have emerged as promising candidates in high-performance sensor and imaging systems. Concise approaches to the synthesis of such molecules are urgently required both for fundamental research and technological applications. In this study, a new symmetric ligand of di(2-hydroxyphenyl)phthalazine with multiple binding sites around a phthalazine unit was readily synthesized, which could be converted efficiently into an asymmetric luminogen (OBNDHPP) through the formation of oxygen-boron-nitrogen bonding. This molecule has a twistable it-extended backbone with a tetracoordinated boron core bearing two bulky phenyl groups, giving it abundant optical properties including a large Stokes shift piezochromism and aggregationinduced emission enhancement. Importantly, the presence of a free phenolic hydroxyl group in the backbone of OBN-DHPP enables the incorporation of various functional moieties into the asymmetric luminogen. As an example, polyethylene glycol (PEG)-modified luminogen (OBN-DHPP-PEG(45)) was synthesized. In the aqueous medium, OBN-DHPP-PEG(45) could self-assemble into spherical nanoparticles with low cytotoxicity and excellent emission performance as well as high solubility. The results of flow cytometry and fluorescence microscopy reveal that these nanoparticles could be internalized successfully by HeLa cells, demonstrating their potential application in bioimaging.

  DOI：

  10.1021/acs.joc.8b01340

文献信息

• Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand
  作者：Feng Qiu、Ning Zhang、Ruizhi Tang、Mingan Zhou、Yao Wang、Weiwei Wei、Shuai Bi、Sheng Han、Fan Zhang

  DOI：10.1021/acs.joc.8b01340

  日期：2018.11.2

  Multifunction luminogens have emerged as promising candidates in high-performance sensor and imaging systems. Concise approaches to the synthesis of such molecules are urgently required both for fundamental research and technological applications. In this study, a new symmetric ligand of di(2-hydroxyphenyl)phthalazine with multiple binding sites around a phthalazine unit was readily synthesized, which could be converted efficiently into an asymmetric luminogen (OBNDHPP) through the formation of oxygen-boron-nitrogen bonding. This molecule has a twistable it-extended backbone with a tetracoordinated boron core bearing two bulky phenyl groups, giving it abundant optical properties including a large Stokes shift piezochromism and aggregationinduced emission enhancement. Importantly, the presence of a free phenolic hydroxyl group in the backbone of OBN-DHPP enables the incorporation of various functional moieties into the asymmetric luminogen. As an example, polyethylene glycol (PEG)-modified luminogen (OBN-DHPP-PEG(45)) was synthesized. In the aqueous medium, OBN-DHPP-PEG(45) could self-assemble into spherical nanoparticles with low cytotoxicity and excellent emission performance as well as high solubility. The results of flow cytometry and fluorescence microscopy reveal that these nanoparticles could be internalized successfully by HeLa cells, demonstrating their potential application in bioimaging.