Synthesis and functionalization of cyclic poly(hydroxystyrene) derivatives

PMSE 247

Boyd A. Laurent, blaurent@tulane.edu and Scott Michael Grayson, sgrayson@tulane.edu. Department of Chemistry, Tulane University, 2015 Percival Stern Hall, New Orleans, LA 70118
Historically, one particular polymer architecture which has been difficult to prepare in high yields and purity is the monocyclic polymer structure. We now report the synthesis of cyclic poly(4-acetoxystyrene) (PAS) through “click” cyclization of the α,ω-difunctionalized linear analogue. Critical to the success of this technique is the use of a slow addition via syringe pump of the linear precursors to a solution containing the “click” cyclization catalyst. The formed cyclic PAS is subsequently converted to cyclic poly(hydroxystyrene) (PHS) through deprotection of the acetate protecting groups. Investigations into the ester anhydride dendronization and functionalization of these cyclic PHS derivatives are presented within.