N-[7-[4-[7-[[[4-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3,5-bis[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]phenyl]-hydroxymethylidene]amino]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-2,1,3-benzothiadiazol-7-yl]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-3,4,5-tridodecoxybenzenecarboximidic acid | 1338564-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-[7-[4-[7-[[[4-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3,5-bis[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]phenyl]-hydroxymethylidene]amino]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-2,1,3-benzothiadiazol-7-yl]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-3,4,5-tridodecoxybenzenecarboximidic acid
• CAS: 1338564-94-5
• 化学式: C₁₅₆H₂₄₉N₇O₂₃S
• 分子量: 2622.79
• InChiKey: PJUAKEKMVNSLGV-URYNFZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  44.2
• 重原子数：
  187
• 可旋转键数：
  121
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  320
• 氢给体数：
  2
• 氢受体数：
  28

反应信息

• 作为产物：
  描述：

  、 C₁₁₅H₁₇₈N₄O₄S 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以84 mg的产率得到N-[7-[4-[7-[[[4-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3,5-bis[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]phenyl]-hydroxymethylidene]amino]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-2,1,3-benzothiadiazol-7-yl]-9,9-bis[(3S)-3,7-dimethyloctyl]fluoren-2-yl]-3,4,5-tridodecoxybenzenecarboximidic acid
  参考文献：
  名称：

  Pre- and Postfunctionalized Self-Assembled π-Conjugated Fluorescent Organic Nanoparticles for Dual Targeting

  摘要：

  There is currently a high demand for novel approaches to engineer fluorescent nanoparticles with precise surface properties suitable for various applications, including imaging and sensing. To this end, we report a facile and highly reproducible one-step method for generating functionalized fluorescent organic nanoparticles via self-assembly of prefunctionalized pi-conjugated oligomers. The engineered design of the nonionic amphiphilic oligomers enables the introduction of different ligands at the extremities of inert ethylene glycol side chains without interfering with the self-assembly process. The intrinsic fluorescence of the nanoparticles permits the measurement of their surface properties and binding to dye-labeled target molecules via Forster resonance energy transfer (FRET). Co-assembly of differently functionalized oligomers is also demonstrated, which enables the tuning of ligand composition and density. Furthermore, nanoparticle prefunctionalization has been combined with subsequent postmodification of azide-bearing oligomers via click chemistry. This allows for expanding ligand diversity at two independent stages in the nanoparticle fabrication process. The practicability of the different methods entails greater control over surface functionality. Through labeling with different ligands, selective binding of proteins, bacteria, and functionalized beads to the nanoparticles has been achieved. This, in combination with the absence of unspecific adsorption, clearly demonstrates the broad potential of these nanoparticles for selective targeting and sequestration. Therefore, controlled bifunctionalization of fluorescent pi-conjugated oligomer nanoparticles represents a novel approach with high applicability to multitargeted imaging and sensing in biology and medicine.

  DOI：

  10.1021/ja2075345