<4-(10'-Phenothiazinyl)but-1-yl>trimethylammonium Bromide | 130904-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: <4-(10'-Phenothiazinyl)but-1-yl>trimethylammonium Bromide
• 英文别名: trimethyl(4-phenothiazin-10-ylbutyl)azanium;bromide
• CAS: 130904-78-8
• 化学式: Br*C₁₉H₂₅N₂S
• 分子量: 393.391
• InChiKey: ZHUYIKDFZGCIOZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  10-(4-bromobutyl)-10H-phenothiazine 、 三甲胺 以 乙腈 为溶剂， 生成 <4-(10'-Phenothiazinyl)but-1-yl>trimethylammonium Bromide
  参考文献：
  名称：

  在阳离子二十八烷基二甲基氯化铵，中性二棕榈酰磷脂酰胆碱和阴离子磷酸二十六烷基酯囊泡中带正电荷和负电荷的中性烷基吩噻嗪的光电离的比较电子自旋共振和电子自旋回波调制研究

  摘要：

  Positively charged phenothiazine N-alkyltrimethylammonium bromides (PC(n)TAB) and negatively charged sodium phenothiazine-N-alkanesulfonates (PC(n)S) were synthesized and photoionized in cationic dioctadecyldimethylammonium chloride (DODAC), neutral dipalmitoylphosphatidylcholine (DPPC), and anionic dihexadecyl phosphate (DHP) vesicles. The photoproduced radicals were identified and quantitated with electron spin resonance. The microenvironments of the various photoproduced PC(n)S and PC(n)TAB cation radicals in frozen D2O solutions were investigated with electron spin echo modulation (ESEM). These results are compared with those of neutral N-alkylphenothiazines (PC(n)) in the same vesicles. The effects of the pendent alkyl chain length on the photoyields of PC(n)S and PC(n)TAB are similar. For short alkyl chains (n = 2 or 3), a large deuteron modulation depth is observed, which correlates with a high photoyield. The large deuteron modulation depth indicates a short interaction distance between the phenothiazine radical and water at the interface. As the alkyl chain length of the anionic and cationic types of phenothiazines increases, the photoyield decreases reaching a minimum near six carbons. The decreased deuteron modulation depth indicates that the increased hydrophobic interaction of the phenothiazine alkyl chain with the vesicle surfactant alkyl chains pulls the phenothiazine group toward the interior of the vesicles, which results in a decrease of the photoyield. At still longer alkyl chain lengths (n = 12), the photoyield increases. This is explained by alkyl chain bending so that the phenothiazine moiety moves toward the vesicle interface region, which results in an increased photoyield. The effects of the pendent alkyl chain length of PC(n)TAB and PC(n)S contrast with those of PC(n) in the same vesicles. As the alkyl chain length of PC(n) increases, the photoyield decreases monotonically in DHP and DPPC vesicles with no evidence of alkyl chain bending. These photoyields are well supported by the ESEM results. In DODAC vesicles the photoyields and deuteron modulation depths decrease up to twelve carbons and then increase which is consistent with some alkyl chain bending. Overall, the photoionization yields and deuteron modulation depths show good self-consistency for all systems studied. For the same vesicle system the photoyields decrease in the order PC(n)S > PC(n)TAB > PC(n). This is explained by the greater hydrophilicity of the sulfonate group of PC(n)S relative to the trimethylammonium group in PC(n)TAB relative to the methyl group of PC(n). This difference locates the phenothiazine moiety closer to the interface region of the vesicles for greater hydrophilicity. These distance differences are verified by the ESE deuteron modulation depths. The photoyields for a given alkylphenothiazine series in the three different vesicles decrease as DODAC > DPPC > DHP. This constrasts with ESE deuteron modulation depths which decrease as DHP > DPPC > DODAC. This indicates that the photoyield for the same alkylphenothiazines in different vesicles is determined primarily by the energy barrier of the vesicle interface charge.

  DOI：

  10.1021/j100111a049