Synthesis and photophysical properties of water-soluble fluorinated poly(aryleneethynylene)s

Herein, we report the synthesis of a new type of poly(aryleneethynylene) (PAE) comprising electron-deficient tetrafluoroarene units in the π-conjugated backbone and water-solubilizing oligoether (OE) side chains. The fluorinated PAEs were synthesized using a transition-metal-free polymerization system promoted by fluoride anions. Long OE side chains typically retard the polymerization. However, this is resolved by using a tBuOK initiator with a large excess of cryptand-222. The present fluorinated PAEs display spectrophotometrically sufficient solubility in water, high fluorescence quantum yields, and reductive fluorescence quenching by arylamines.