Synthesis of chromo- and fluorogenic poly(ortho-diaminophenylene) chemosensors for fluoride anion

Two new poly(ortho-diaminophenylene) derivatives containing fluorene and/or quinoxaline moieties per repeat unit in the main chain were synthesized via Suzuki coupling reaction followed by reduction process. The synthesized polymers were characterized and explored as colorimetric and fluorometric anion-sensing materials. The polymers in dilute tetrahydrofuran (THF) solution emitted green light (about 530 nm) in their precursor benzothiadiazole forms and blue to green light (477-523 nm) in their reduced forms. The color of polymer solution was dramatically altered upon addition of fluoride anion without noticeable absorption change in UVvis spectrum. The fluorescence was ratiometrically quenched with a linear relationship between fluorescence intensity and fluoride anion concentration implying static quenching mechanism could be applied judging from the maintenance of constant fluorescence lifetime with variable fluoride anion concentration. (c) 2006 Wiley Periodicals, Inc.