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

Abstract

In the present work, pyrene-boron-dipyrromethene (BODIPY)-substituted novel water-soluble cyclotriphosphazene derivatives (6 and 7) were synthesized by click reactions between a cyclotriphosphazene derivative with a hydrophilic glycol side group (2) and BODIPYs (4 and 5). All of the new compounds (2, 6, and 7) were characterized by Fourier-transform infrared and nuclear magnetic resonance spectroscopy, as well as mass spectrometry and elemental analysis. The photophysical properties of the BODIPY-substituted cyclotriphosphazenes (6 and 7) were investigated by UV-Vis and fluorescence emission spectroscopy in water and water/solvent mixtures. It was found that the target compounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.

Synthesis, characterization, and photophysical and fluorescence sensor behaviors of a new water-soluble double-bridged naphthalene diimide appended cyclotriphosphazene

“…In addition, resulting rigid cores have been used for the application of electroluminescent devices because it is known that this type of materials can demonstrate amorphous properties [ 6 , 7 ]. The water-solubility of fluorescence compounds is a desired property, especially in sensor applications because the analysis medium in environmental or biological samples consists of water [ 8 ]. Although cyclotriphosphazene cores demonstrate extraordinary chemical and physical properties, they mainly do not dissolve in water, whereas they are highly soluble in organic solvents.…”

“…Although cyclotriphosphazene cores demonstrate extraordinary chemical and physical properties, they mainly do not dissolve in water, whereas they are highly soluble in organic solvents. When considering the effect of water on fluorescence intensity, the weak water solubility of cyclotriphosphazene-based fluorescence materials limited their luminescence applications [ 8 ]. For cyclotriphosphazene, having reactive six Cl-atoms, researchers have tried to overcome this problem recently by modifying phosphazenes with water-soluble groups together with fluorescent dyes [ 9 – 12 ].…”