Synthesis and characterization of poly(tetraphenylimidazole)s and their application in the detection of fluoride ions

Here, we describe the synthesis and characterization of a silyl protected tetraphenylimidazole monomer and its homo and co-polymer. The requisite monomer was accessed by Suzuki–Miyaura cross-coupling of 2-(1-(4-bromophenyl)-4,5-diphenyl-1H-imidazol-2-yl)phenol and 4-vinylphenylboronic acid followed by protection of the phenolic group by tert-butyl(chloro)diphenylsilane. The desired polymers were readily synthesized by using free radical polymerization. Both the polymers and monomer were characterized using different analytical techniques including multinuclear NMR, GPC (for polymers), and single crystal X-ray crystallography (for the monomer). By utilizing the greater fluorophilicity of the silyl atom, the polymers were studied as probes for the detection of fluoride ions. The selectivity and sensitivity of the synthesized polymers were investigated in detail.