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Updated: Dec 20, 2025

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Building Shape-Persistent Arylene Ethynylene Macrocycles as Scaffolds for 1,4-Diiodobutadiyne
Bin Sun1, Daniel M Lux1, Eric V Patterson1
1Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, United States.
Abstract:
Two shape-persistent arylene ethynylene macrocycles have been designed and synthesized as scaffolds to bind the nonpolar molecule 1,4-diiodobutadiyne. Binding via halogen bonding interactions between the pyridine moieties of the macrocycle and 1,4-diiodobutadiyne is predicted by density functional theory calculations and has been demonstrated in solution by 13C NMR titrations. The binding constant for the macrocycle-monomer complex (K = 10.5 L mol-1) is much larger than for other comparable halogen bonds, strongly supporting cooperative binding of both ends of the diyne. These results demonstrate a fully inserted geometry of 1,4-diiodobutadiyne in the complex.
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