N-[[3',6'-bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]carbamothioyl]prop-2-enamide | 1190770-87-6

• 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: N-[[3',6'-bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]carbamothioyl]prop-2-enamide
• CAS: 1190770-87-6
• 化学式: C₃₂H₃₅N₅O₃S
• 分子量: 569.728
• InChiKey: WFPHOYKPYHWBTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  acryloyl isothiocyanate 、 若丹明B酰肼 以 乙腈 为溶剂， 反应 25.0h， 以72%的产率得到N-[[3',6'-bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]carbamothioyl]prop-2-enamide
  参考文献：
  名称：

  Hg²⁺-Reactive Double Hydrophilic Block Copolymer Assemblies as Novel Multifunctional Fluorescent Probes with Improved Performance

  摘要：

  We report on novel type of responsive double hydrophilic block copolymer (DHBC)-based multifunctional chemosensors to Hg2+ ions, pH, and temperatures and investigate the effects of thermo-induced micellization on the detection sensitivity. Well-defined DHBCs bearing rhodamine B-based Hg2+-reactive moieties (RhBHA) in the thermoresponsive block, poly(ethylene oxide)-b-poly(N-isopropylacrylamide-co-RhBHA) (PEO-b-P(NIPAM-co-RhBHA)), were synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Nonfluorescent RhBHA moieties are subjected to selective ring-opening reaction upon addition of Hg2+ ions or lowering solution pH, producing highly fluorescent acyclic species. Thus. at room temperature PEO-h-P(NIPAM-co-RhBHA) DHBCs can serve as water-soluble multifunctional and efficient fluorescent chemosensors to Hg2+ ions and pH. Upon heating above the lower critical solution temperature (similar to 36 degrees C) of the PNIPAM block, they self-assemble into micelles possessing P(NIPAM-co-RhBHA) cores and well-solvated PEO coronas, which were fully characterized by dynamic and static laser light scattering. It was found that the detection sensitivity to Hg2+ ions and pH could be dramatically improved at elevated temperatures due to fluorescence enhancement of RhBHA residues in the acyclic form, which were embedded within hydrophobic cores of thermo-induced micellar aggregates. This work represents a proof-of-concept example of responsive DHBC-based multifunctional fluorescent chemosensors for the highly efficient detection of Hg2+ ions, pH, and temperatures with tunable detection sensitivity. Compared to reaction-based small molecule Hg2+ probes in previous literature reports, the integration of stimuli-responsive block copolymers with well-developed small molecule-based selective sensing moieties in the current study are expected to exhibit preferred advantages including enhanced detection sensitivity, water dispersibility, biocompatibility, facile incorporation into devices, and the ability of further functionalization for targeted imaging and detection.

  DOI：

  10.1021/la9024102