Temperature-controlled release of catechol dye in thermosensitive phenylboronate-containing copolymers: A quantitative study

The reversible complex formation between two phenylboronic acid bearing copolymers and the catechol dye Alizarin Red S (ARS) was studied by dialysis experiments coupled with UV–visible spectroscopy. The first copolymer based on N-isopropylacrylamide (NIPAM) is thermosensitive, whereas the second one based on N,N-dimethylacrylamide (DMAM) is not. The investigation resulted in the quantitative determination of the host–guest binding constants at two different temperatures at pH 7.4 in phosphate buffer. Above the phase transition temperature Tp of the thermosensitive copolymer, the binding constant decreases by a factor of 6, twice more than in the case of the non-thermosensitive copolymer. This behaviour is related to the coil-to-globule transition of NIPAM-based copolymer, which above Tp expels the dye marker.