(E)-9,9-didecyl-7-(4-(dibutylamino)styryl)-9H-fluorene-2-carbaldehyde | 1228700-07-9

• 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: (E)-9,9-didecyl-7-(4-(dibutylamino)styryl)-9H-fluorene-2-carbaldehyde
• 英文别名: 9,9-didecyl-7-[(E)-2-[4-(dibutylamino)phenyl]ethenyl]fluorene-2-carbaldehyde
• CAS: 1228700-07-9
• 化学式: C₅₀H₇₃NO
• 分子量: 704.136
• InChiKey: GFPAUAYNBAGLKW-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.5
• 重原子数：
  52
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetraethyl 4,4'-(benzo[1,2-d:4,5-d']bisthiazole-2,6-diyl)bisbenzylphosphonate 、 (E)-9,9-didecyl-7-(4-(dibutylamino)styryl)-9H-fluorene-2-carbaldehyde 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以43%的产率得到N,N-dibutyl-4-[(E)-2-[9,9-didecyl-7-[(E)-2-[4-[2-[4-[(E)-2-[9,9-didecyl-7-[(E)-2-[4-(dibutylamino)phenyl]ethenyl]fluoren-2-yl]ethenyl]phenyl]-[1,3]thiazolo[5,4-f][1,3]benzothiazol-6-yl]phenyl]ethenyl]fluoren-2-yl]ethenyl]aniline
  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
• 作为产物：
  描述：

  7-bromo-9,9-di-n-decyl-9H-fluorene-2-carboxaldehyde 、 N,N-dibutyl-4-vinylaniline 在 四丁基氯化铵 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到(E)-9,9-didecyl-7-(4-(dibutylamino)styryl)-9H-fluorene-2-carbaldehyde
  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

文献信息

• Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging
  作者：Sheng Yao、Hyo-Yang Ahn、Xuhua Wang、Jie Fu、Eric W. Van Stryland、David J. Hagan、Kevin D. Belfield

  DOI：10.1021/jo100554j

  日期：2010.6.18

  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.