Çiftçi Gönül Yenilmez, Şenkuytu Elif, Bulut Mustafa, Durmuş Mahmut
Department of Chemistry, Gebze Technical University, Gebze, 41400, Kocaeli, Turkey.
Faculty of Art and Science, Department of Chemistry, Marmara University, Kadıköy, 34722, Istanbul, Turkey.
J Fluoresc. 2015 Nov;25(6):1819-30. doi: 10.1007/s10895-015-1672-4. Epub 2015 Sep 29.
In the present work, 3-[2-(diethylamino)ethyl]-7-oxy-4-methylcoumarin substituted cyclotriphosphazene (4) and cyclotetraphosphazene (5) derivatives were synthesized by the reactions of hexachlorocyclotriphosphazene (1) or octachlorocyclotetraphosphazene (2) with 3-[2-(diethylamino)ethyl]-7-hydroxy-4-methylcoumarin (3) for the first time. The quaternized cationic (6 and 7) and zwitterionic (8 and 9) derivatives of these compounds (4 and 5) were obtained by the reactions of dimethyl sulfate and 1,3-propanesultone, respectively. All newly synthesized cyclophosphazene compounds (4-9) were fully characterized by elemental analysis and general spectroscopic techniques such as FT-IR, (31)P-NMR, (1)H-NMR and MALDI-TOF mass. All these coumarin substituted cyclophosphazene compounds (4-9) were soluble in most of organic solvents and quaternized ionic and zwitterionic compounds (6-9) also showed excellent solubility in water. The fluorescence behaviors of novel cyclophosphazene compounds were investigated in methanol and water solutions. The chemosensor properties of newly synthesized water soluble quaternized ionic and zwitterionic cyclotriphosphazene and cyclotetraphosphazene derivatives (6-9) were investigated in aqueous media. These cyclophosphazene derivatives showed fluorescence chemosensor behavior with high selectivity for Fe(3+) ions in aqueous solution.
在本工作中，首次通过六氯环三磷腈（1）或八氯环四磷腈（2）与3-[2-(二乙氨基)乙基]-7-羟基-4-甲基香豆素（3）反应合成了3-[2-(二乙氨基)乙基]-7-氧代-4-甲基香豆素取代的环三磷腈（4）和环四磷腈（5）衍生物。这些化合物（4和5）的季铵化阳离子衍生物（6和7）和两性离子衍生物（8和9）分别通过硫酸二甲酯和1,3-丙烷磺内酯反应得到。所有新合成的环磷腈化合物（4-9）均通过元素分析以及FT-IR、(31)P-NMR、(1)H-NMR和MALDI-TOF质谱等常规光谱技术进行了全面表征。所有这些香豆素取代的环磷腈化合物（4-9）可溶于大多数有机溶剂，季铵化离子型和两性离子型化合物（6-9）在水中也表现出优异的溶解性。研究了新型环磷腈化合物在甲醇和水溶液中的荧光行为。在水介质中研究了新合成的水溶性季铵化离子型和两性离子型环三磷腈和环四磷腈衍生物（6-9）的化学传感器性能。这些环磷腈衍生物在水溶液中对Fe(3+)离子表现出具有高选择性的荧光化学传感器行为。
