5-[2-[15,24-Bis[2-(3,5-dicarboxyphenyl)ethynyl]-9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12(17),13,15,19,21(26),22,24-dodecaenyl]ethynyl]benzene-1,3-dicarboxylic acid | 1353566-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-[2-[15,24-Bis[2-(3,5-dicarboxyphenyl)ethynyl]-9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12(17),13,15,19,21(26),22,24-dodecaenyl]ethynyl]benzene-1,3-dicarboxylic acid
• 英文别名: 5-[2-[15,24-bis[2-(3,5-dicarboxyphenyl)ethynyl]-9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12(17),13,15,19,21(26),22,24-dodecaenyl]ethynyl]benzene-1,3-dicarboxylic acid
• CAS: 1353566-92-3
• 化学式: C₈₇H₉₀O₂₄
• 分子量: 1519.66
• InChiKey: LVIOEZKSXOMJRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  111
• 可旋转键数：
  48
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  335
• 氢给体数：
  6
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  Dimethyl 5-[2-[15,24-bis[2-[3,5-bis(methoxycarbonyl)phenyl]ethynyl]-9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12(17),13,15,19,21(26),22,24-dodecaenyl]ethynyl]benzene-1,3-dicarboxylate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到5-[2-[15,24-Bis[2-(3,5-dicarboxyphenyl)ethynyl]-9,9,18,18,27,27-hexakis[2-(2-methoxyethoxy)ethyl]-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12(17),13,15,19,21(26),22,24-dodecaenyl]ethynyl]benzene-1,3-dicarboxylic acid
  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.