1. Phthalocrowns: Isoindoline-Crown Ether Macrocycles.
- Author
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Tamgho, Ingrid-Suzy, Engle, James T., and Ziegier, Christopher J.
- Subjects
- *
CROWN ethers , *MACROCYCLIC compounds , *HETEROCYCLIC compounds , *MACROMOLECULES , *POLYETHERS - Abstract
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]
- Published
- 2012
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