Synthesis of Poly(phenyltriazolylcarboxylate)s with Aggregation-Induced Emission Characteristics by Metal-Free 1,3-Dipolar Polycycloaddition of Phenylpropiolate and Azides.

Two soluble poly(phenyltriazolylcarboxylate)s (PPTCs) with high molecular weights (M w up to 26 800) are synthesized by the metal-free 1,3-dipolar polycycloadditions of 4,4'-isopropylidenediphenyl diphenylpropiolate (1) and tetraphenylethene-containing diazides (2) in dimethylformamide at 150 °C for 12 h in high yields (up to 93%). The resultant polymers are soluble in common organic solvents and are thermally stable with 5% weight loss temperatures higher than 375 °C. The PPTCs are nonemissive in solutions, but become highly luminescent upon aggregation, showing a phenomenon of aggregation-induced emission. Their aggregates can be used as fluorescent chemosensors for high-sensitivity detection of explosives.