5-(trimethylstannyl)-4,4-bis(6-bromohexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene | 1572225-13-8

• 分子结构分类: 有机化合物
• 英文名称: 5-(trimethylstannyl)-4,4-bis(6-bromohexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• CAS: 1572225-13-8
• 化学式: C₂₄H₃₆Br₂S₂Sn
• 分子量: 667.2
• InChiKey: KZKHRRYBLXPDAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.31
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7,7'-(4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene-2,6-diyl)bis(4-bromobenzo[1,2,5]thiadiazole) 、 5-(trimethylstannyl)-4,4-bis(6-bromohexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 0.85h， 以68%的产率得到7,7'-(4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene-2,6-diyl)bis(4-(4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)benzo[c][1,2,5]thiadiazole)
  参考文献：
  名称：

  Synthesis, Characterization, and Biological Affinity of a Near-Infrared-Emitting Conjugated Oligoelectrolyte

  摘要：

  A near-IR-emitting conjugated oligoelectrolyte (COE), ZCOE, was synthesized, and its photophysical features were characterized. The biological affinity of ZCOE is compared to that of an established lipid-membrane-intercalating COE, DSSN+, which has blue-shifted optical properties making it compatible for tracking preferential sites of accumulation. ZCOE exhibits diffuse staining of E. coli cells, whereas it displays internal staining of select yeast cells which also show propidium iodide staining, indicating ZCOE is a "dead" stain for this organism. Staining of mammalian cells reveals complete internalization of ZCOE through endocytosis, as supported by colocalization with LysoTracker and late endosome markers. In all cases DSSN+ persists in the outer membranes, most likely due to its chemical structure more closely resembling a lipid bilayer.

  DOI：

  10.1021/ja412695w
• 作为产物：
  描述：

  1,6-二溴己烷 在 正丁基锂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 5-(trimethylstannyl)-4,4-bis(6-bromohexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  Synthesis, Characterization, and Biological Affinity of a Near-Infrared-Emitting Conjugated Oligoelectrolyte

  摘要：

  A near-IR-emitting conjugated oligoelectrolyte (COE), ZCOE, was synthesized, and its photophysical features were characterized. The biological affinity of ZCOE is compared to that of an established lipid-membrane-intercalating COE, DSSN+, which has blue-shifted optical properties making it compatible for tracking preferential sites of accumulation. ZCOE exhibits diffuse staining of E. coli cells, whereas it displays internal staining of select yeast cells which also show propidium iodide staining, indicating ZCOE is a "dead" stain for this organism. Staining of mammalian cells reveals complete internalization of ZCOE through endocytosis, as supported by colocalization with LysoTracker and late endosome markers. In all cases DSSN+ persists in the outer membranes, most likely due to its chemical structure more closely resembling a lipid bilayer.

  DOI：

  10.1021/ja412695w