Selective Self-Assembly of Supramolecular Helices and Macrocycles Directed by Halogen Bonding.

Autor: Hu ZY; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Du M; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Li W; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Huang X; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Ma R; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Li Y; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Shen RZ; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Wang T; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Liu CZ; Henan Engineering Research, Center for Green Synthesis of Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, 55 Pingyuan middle Road, Shangqiu, Henan, 476000, China., Li ZT; Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 11, pp. e202403821. Date of Electronic Publication: 2024 Dec 11.
DOI: 10.1002/chem.202403821
Abstrakt: In this study, several hydrogen-bonded arylamide foldamers (compounds 1-5) with the same degree of polymerization were designed and synthesized. The polyfluoroiodobenzene or iodoethynyl polyfluoroiodobenzene segment was modified as a halogen donor at the end of the monomer, and pyridine or pyridine oxynitride served as the corresponding halogen acceptor segment. The crystal structure of compound 1 indicates that the supramolecular double helices were constructed by stacking a P helix and an M helix in an antiparallel manner in the direction of intermolecular I⋅⋅⋅ - O-N + halogen bonding. The zig-zag-shaped linear structures of compounds 2 and 3 were generated under the induction of intermolecular I⋅⋅⋅N and I⋅⋅⋅ - O-N + halogen bonds. [1+1] near-planar bimolecular supramolecular macrocycles in compounds 4 and 5 were formed by multiple groups of effective intramolecular three-center hydrogen bonding and strong I⋅⋅⋅N and I⋅⋅⋅ - O-N + halogen bonds. Hirshfeld surface analysis and theoretical modelling of the halogen bonding energy were performed. The noncovalent interactions on the surface of the monomers and the halogen bonding energy were investigated in detail.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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