Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding

Liu, Chuan-Zhi; Zhang, Chi; Li, Zhong-Yi; Chen, Jiale; Wang, Tonglu; Zhang, Xiang-Kun; Yan, Meng; Zhai, Bin

doi:10.1039/d4cc01472c

Chem. Commun.

2024

DOI: 10.1039/d4cc01472c

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Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding

Chuan-Zhi Liu,

Chi Zhang,

Zhong-Yi Li

et al.

Abstract: In this study, benzoselenadiazole-pyridine-bifunctionalized hydrogen-bonded arylamide foldamer was synthesized. The co-crystallization experiment with 1,4-diiodotetrafluorobenzene showed that: a new type of supramolecular double helices, which was induced by triple orthogonal interaction...

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Cited by 2 publications

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

Hu,

Du,

et al. 2024

Chemistry A European J

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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.

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

Hu,

Du,

et al. 2024

Chemistry A European J

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Non‐Covalent Interactions Directed Supramolecular Helices from H‐bonded Building Blocks

Liu,

Hou,

Zhang

et al. 2024

Eur J Inorg Chem

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Chemists have developed sophisticated structural monomers and meticulously regulated the strength and directionality of non‐covalent interactions to assemble a variety of novel supramolecular helices in accordance with the second strategy, resulting in significant research advancements. These investigations not only enhance our comprehension of the supramolecular assembly process but also inspire innovative approaches for the development of supramolecular materials and related domains within materials chemistry. In the strategy for constructing supramolecular helices, utilizing non‐covalent interactions between monomers as a bonding force is an effective method for further assembling monomeric units with H‐bonded meniscus structures into helical configurations. Hydrogen and and halogen bonds represent two distinct categories of non‐covalent interactions that have increasingly attracted scholarly attention in recent years, demonstrating extensive and significant applications in the assembly of diverse supramolecular topologies. This paper provides a summary of several instances where these interactions facilitate the self‐assembly of supramolecular helices. Moreover, although the development of chalcogen bonding has emerged relatively recently compared to their counterparts, and despite their limited application in complex assembly structures, they have nonetheless been effectively employed in the construction of supramolecular helices.

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Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding

Cited by 2 publications

References 49 publications

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

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

Non‐Covalent Interactions Directed Supramolecular Helices from H‐bonded Building Blocks

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