4,4'-(1E,1'E)-2,2'-(9,9-didecyl-4,5-dinitro-9H-fluorene-2,7-diyl)bis(ethene-2,1-diyl)bis(N,N-dibutylaniline) | 1228699-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4'-(1E,1'E)-2,2'-(9,9-didecyl-4,5-dinitro-9H-fluorene-2,7-diyl)bis(ethene-2,1-diyl)bis(N,N-dibutylaniline)
• 英文别名: N,N-dibutyl-4-[(E)-2-[9,9-didecyl-7-[(E)-2-[4-(dibutylamino)phenyl]ethenyl]-4,5-dinitrofluoren-2-yl]ethenyl]aniline
• CAS: 1228699-98-6
• 化学式: C₆₅H₉₄N₄O₄
• 分子量: 995.486
• InChiKey: FWPYZQDGPDZONQ-FMWAKIAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  73
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9,9-didecyl-4,5-dinitro-9H-fluorene-2,7-dicarbaldehyde 、 4-(N,N’-dibutylaminobenzyl)triphenylphosphonium iodide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到4,4'-(1E,1'E)-2,2'-(9,9-didecyl-4,5-dinitro-9H-fluorene-2,7-diyl)bis(ethene-2,1-diyl)bis(N,N-dibutylaniline)
  参考文献：
  名称：

  Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging

  摘要：

  As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor- acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high-yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic F 108N F micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization (> 0.98 colocalization coefficient) relative to commercial Lysotracker Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging.

  DOI：

  10.1021/jo100554j