Phthalocrowns: Isoindoline-Crown Ether Macrocycles.

The reaction of diiminoisoindoline with amine-terminated polyethers results in the formation of phthalocrown macrocycles. For n = 1 (where n is the number of ether units), a 2 + 2 condensation takes place, but for n = 2 and 3, a 1 + 1 macrocyde formation occurs. The n = 2 phthalocrown is particularly stable due to a strong intramolecular hydrogen bond, but the n = 3 ring hydrolyzes to form a 3-imino-l-oxoisoindoline derivatized crown ether species. For the n = 1 phthalocrown, we observed dynamic behavior in the ¹H NMR spectrum, and using VTNMR were able to measure a ΔG = 44.6 kJ/mol for proton exchange. [ABSTRACT FROM AUTHOR]