ABSTRACT
Abstract-Novel macrocycles containing 1-amino-4,5-8-naphthalenetricarboxylic acid-l,8-lactam4,5-imide and 1,4,5-8-naphthalenetetracarboxylic bisimide fragments have been synthesized by the high temperature pseudo high dilution acylation of the corresponding diols with isopththaloyl chlo ride, 4,4’- and 2,2’-dichlorocarbonyl biphenyls with up to 60% yield. An important side reaction that impedes cyclization was found to be the reaction of diol OH groups with HC1 during the acyla tion. The ring strain in synthesized macrocycles and model cycles was estimated using the isodesmic reaction approach at B3LYP/6-31 l+G(d,p)//HF/3-21G level of theory. Lactamimide containing macrocycles were found to be more strained as compared to those containing bisimide. The ring opening polymerization (ROP) of synthesized macrocycles in the molten state shows that the driv ing force for this process is the strain release on ring opening. The ROP of lactamimide containing macrocycles was found to be an efficient way to obtain lactamimide containing polymers, otherwise difficult to synthesize.
