Novel Coumarin Substituted Water Soluble Cyclophosphazenes as “Turn-Off” Type Fluorescence Chemosensors for Detection of Fe3+ ions in Aqueous Media

Abstract

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.

RETRACTED ARTICLE: Synthesis and characterization of trimeric phosphazene based ionic liquids with tetrafluoroborate anions and their thermal investigations

“…The PzILs with different anions (chloride, Cl − , bis-trifluoromethane sulfonimide, NTf 2 − and tetrafluoroborate, BF 4 − ) were obtained by simple anion exchange reactions 17 , 20 – 25 . On the other hand, PzILs with various molecular weights or different average chain lengths have been used as antibacterial, antifungal and anticancer agents 5 , 6 , 13 – 15 , lubricants 17 , 25 , adsorbents and surface modifiers 18 , a gate dielectric layer for OFETs 20 , 21 , electrolyte solutions 19 , 23 , 24 and chemosensors for metal ions 26 .…”

Phosphazene-Based Ionic Liquids

“…Quaternized ionic and zwitterionic compounds display excellent solubility in water and the effects of metal ions on the fluorescent behavior of the cytophosphazene salts were investigated using these compounds as chemosensors for metal ions. The results showed that cyclophosphazenium salts exhibit highly selective fluorescence chemosensor behavior for Fe 3+ ions in aqueous solution [38].…”

“…PzILs are prepared by quaternization of a wide variety of phosphazenes either at the sidegroup or at the skeletal nitrogen atoms. These ILs have been used as anticancer, antibacterial reagents [31][32][33][34], adsorbents and surface modifiers of fluorescent nanoparticles [35], lubricants [36,37], chemosensors for metal ions [38], electrolyte solutions for energy storage devices [39][40][41], as gate dielectric layer for OFETs [42], or as polyelectrolytes [26,43,44].…”

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

“…In order to make these compounds water-soluble, hydrophilic groups should be present in the molecular structure. There are several examples of water-soluble phosphazenes in the literature, but to the best of our knowledge, most of them are focused on polyphosphazenes [23][24][25][26][27][28]. Thus, the design and synthesis of water-soluble cyclotriphosphazene compounds is particularly important for studies in aqueous media.…”