5,5',10,10',15,15'-hexa-2-(2-methoxyethoxy)ethyltruxene | 1353566-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5,5',10,10',15,15'-hexa-2-(2-methoxyethoxy)ethyltruxene
• 英文别名: 9,9,18,18,27,27-Hexakis[2-(2-methoxyethoxy)ethyl]heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3,5,7,10,12,14,16,19,21,23,25-dodecaene；9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3,5,7,10,12,14,16,19,21,23,25-dodecaene
• CAS: 1353566-84-3
• 化学式: C₅₇H₇₈O₁₂
• 分子量: 955.239
• InChiKey: HSWWIZAEJJTWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  69
• 可旋转键数：
  36
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,5',10,10',15,15'-hexa-2-(2-methoxyethoxy)ethyltruxene 在 potassium iodate 、 碘 作用下， 以 四氯化碳 、 硫酸 、 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以93%的产率得到2,7,12-triiodo-5,5',10,10',15,15'-hexa-2-(2-methoxyethoxy)ethyltruxene
  参考文献：
  名称：

  Water-soluble anionic fluorophores from truxene

  摘要：

  Two new water-soluble fluorophores are synthesized from truxene and ester-substituted aryl acetylenes. The truxene core is decorated by 2-(2'-methoxy)ethoxyethyl groups to enhance the hydrophilicity of these fluorophores as well as to prevent the aggregation by pi-stacking in aqueous media. The conjugated structures are assembled by iodination of the truxene core and subsequent Sonogashira coupling with aryl acetylenes. Upon the hydrolysis of the ester groups, water-soluble fluorophores are obtained in good to excellent yield (30-71% for 3 steps). A photophysical investigation reveals that these compounds exhibit strong fluorescence signals (quantum yield 46-63%) with maximum emission wavelength around 390-400 nm in aqueous phosphate buffer. Preliminary screening on sensing application shows that their fluorescent signals can be selectively quenched by porphyrin-containing metalloproteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.10.009
• 作为产物：
  描述：

  三聚茚 、 1-(2-碘乙氧基)-2-甲氧基乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以66%的产率得到5,5',10,10',15,15'-hexa-2-(2-methoxyethoxy)ethyltruxene
  参考文献：
  名称：

  Water-soluble anionic fluorophores from truxene

  摘要：

  Two new water-soluble fluorophores are synthesized from truxene and ester-substituted aryl acetylenes. The truxene core is decorated by 2-(2'-methoxy)ethoxyethyl groups to enhance the hydrophilicity of these fluorophores as well as to prevent the aggregation by pi-stacking in aqueous media. The conjugated structures are assembled by iodination of the truxene core and subsequent Sonogashira coupling with aryl acetylenes. Upon the hydrolysis of the ester groups, water-soluble fluorophores are obtained in good to excellent yield (30-71% for 3 steps). A photophysical investigation reveals that these compounds exhibit strong fluorescence signals (quantum yield 46-63%) with maximum emission wavelength around 390-400 nm in aqueous phosphate buffer. Preliminary screening on sensing application shows that their fluorescent signals can be selectively quenched by porphyrin-containing metalloproteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.10.009

文献信息

• Water-soluble anionic fluorophores from truxene
  作者：Nopporn Earmrattana、Mongkol Sukwattanasinitt、Paitoon Rashatasakhon

  DOI：10.1016/j.dyepig.2011.10.009

  日期：2012.4

  Two new water-soluble fluorophores are synthesized from truxene and ester-substituted aryl acetylenes. The truxene core is decorated by 2-(2'-methoxy)ethoxyethyl groups to enhance the hydrophilicity of these fluorophores as well as to prevent the aggregation by pi-stacking in aqueous media. The conjugated structures are assembled by iodination of the truxene core and subsequent Sonogashira coupling with aryl acetylenes. Upon the hydrolysis of the ester groups, water-soluble fluorophores are obtained in good to excellent yield (30-71% for 3 steps). A photophysical investigation reveals that these compounds exhibit strong fluorescence signals (quantum yield 46-63%) with maximum emission wavelength around 390-400 nm in aqueous phosphate buffer. Preliminary screening on sensing application shows that their fluorescent signals can be selectively quenched by porphyrin-containing metalloproteins. (C) 2011 Elsevier Ltd. All rights reserved.