FRET interaction between pyrene-tagged β-hydroxy acid and perylen-3-ylmethylmethacrylate co-N-dodecylmethacrylamide in film and solution

Calderon IAC, Lao KS, Chua ET, Romano E, Anore KHS, Cabatuando ACR, Ibabao MJP, Guerrero RA, So RC. 2013. FRET interaction between pyrene-tagged β-hydroxy acid and perylen-3-ylmethylmethacrylate co-N-dodecylmethacrylamide in film and solution. Journal of Applied Polymer Science. 129(5):2865–2872.
 
Synthesis, characterization, and FRET interaction of pyrene-tagged β-hydroxy acid and perylen-3-ylmethylmethacrylate co-N-dodecylmethacrylamide polymer are described. The fluorescent donor, β-hydroxy acid-pyrene boronic ester was synthesized from commercially available alkyl ketene dimer via subsequent hydrolysis, reduction and esterification providing the donor. Conversely, the fluorescent acceptor was synthesized by co-polymerization of N-dodecylmethacryamide and perylen-3-ylmethylmethacrylate, where the latter was prepared from commercially available perylene in three steps. FRET interaction between the donor and acceptor was carried out by titration and monitored using fluorescence spectroscopy. Fluorescence quenching and enhancement in both film and solution formats were observed; furthermore, a more prominent lipophilic-induced interaction was observed in solution. Fluorescence enhancement (at 460 nm) is higher for the acceptor and quenching efficiency (at 420 nm) is higher for donor-acceptor pair, pyrene-tagged β-hydroxy acid and perylen-3-ylmethylmethacrylate co-N-dodecylmethacryl-amide polymer, compared to control, pyrene boronic ester. The quenching is due to dynamic quenching between the donor and acceptor. Furthermore, aggregation was not observed from the pyrene-tagged β-hydroxy acid ester donor as the concentration of the solution is increased up to 3000 ppm.