tetramethylsulforhodamine | 60530-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: tetramethylsulforhodamine
• 英文别名: TMSR；2-[3-(Dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzenesulfonate
• CAS: 60530-00-9
• 化学式: C₂₃H₂₂N₂O₄S
• 分子量: 422.505
• InChiKey: JTPHBZGNPMRYAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dichlorosulfophthalein 、 二甲胺 以 乙醇 为溶剂， 生成 tetramethylsulforhodamine
  参考文献：
  名称：

  7-Azabicyclo[2.2.1]heptane as a Unique and Effective Dialkylamino Auxochrome Moiety: Demonstration in a Fluorescent Rhodamine Dye

  摘要：

  A new type of a highly fluorescent sulforhodamine dye, 221SR, was designed and synthesized using 7-azabicylco[2.2.1]heptyl moieties as the electron donating auxochrome groups. Using the prototypical dye tetramethylsulforhodamine, TMSR, as a benchmark, we show this new dye has higher fluorescent quantum yields, Phi, (Phi = 0.95 vs Phi = 0.65 at 20 degrees C, emission efficiencies that are invariant in the 20 -> 60 degrees C temperature range (Phi = 0.95 vs Phi = 0.38 at 60 degrees C, and fluorescence lifetimes that increase with a rise in temperature (20 -> 60 degrees C) as compared to a decrease for the benchmark dye (3.8 -> 3.9 vs 2.8 -> 1.7 ns). Importantly, photostability studies found the azabicyclic rhodamine to be many times more stable than its tetramethyl analogue. To the best our knowledge this is the first report of the use of an apex-N-substituted azabicycloalkane as an electron donor group in any class of donor-acceptor dye. Thus, the concept of using an apex-substitutes bicyclic amine as a donor moiety constitutes a new paradigm for simultaneously inducing remarkable beneficial effects on both emission efficiency and photostability in a donor-acceptor fluorophore.

  DOI：

  10.1021/ja8075617

文献信息

• 7-Azabicyclo[2.2.1]heptane as a Unique and Effective Dialkylamino Auxochrome Moiety: Demonstration in a Fluorescent Rhodamine Dye
  作者：Xiangzhi Song、Alexis Johnson、James Foley

  DOI：10.1021/ja8075617

  日期：2008.12.31

  A new type of a highly fluorescent sulforhodamine dye, 221SR, was designed and synthesized using 7-azabicylco[2.2.1]heptyl moieties as the electron donating auxochrome groups. Using the prototypical dye tetramethylsulforhodamine, TMSR, as a benchmark, we show this new dye has higher fluorescent quantum yields, Phi, (Phi = 0.95 vs Phi = 0.65 at 20 degrees C, emission efficiencies that are invariant in the 20 -> 60 degrees C temperature range (Phi = 0.95 vs Phi = 0.38 at 60 degrees C, and fluorescence lifetimes that increase with a rise in temperature (20 -> 60 degrees C) as compared to a decrease for the benchmark dye (3.8 -> 3.9 vs 2.8 -> 1.7 ns). Importantly, photostability studies found the azabicyclic rhodamine to be many times more stable than its tetramethyl analogue. To the best our knowledge this is the first report of the use of an apex-N-substituted azabicycloalkane as an electron donor group in any class of donor-acceptor dye. Thus, the concept of using an apex-substitutes bicyclic amine as a donor moiety constitutes a new paradigm for simultaneously inducing remarkable beneficial effects on both emission efficiency and photostability in a donor-acceptor fluorophore.