Intermolecular Halogen Bonding-Controlled Self-Assembly of Hydrogen Bonded Aromatic Amide Foldamers

doi:10.6023/cjoc202102012

Abstract

Six intramolecular hydrogen bonding-induced aromatic amide foldamers have been prepared through the formation of the hydrazone bond in the last step. The compounds are attached with one trifluoroiodobenzene as halogen donor and one pyridine ring as halogen bonding acceptor. Intermolecular I…N halogen bond formed by the above two units and other kinds of halogen bonds are designed to modulate the stacking of the compounds in the solid state. It is revealed that intermolecular halogen bonding can induce the molecules to form extended zigzag arrays, dimeric macrocycles or supramolecular helices. The formation of the dimeric macrocycles is favored when the halogen bond donor and acceptor are located in a parallel manner. Longer tetrameric and pentameric sequences give rise to more curved, crescent conformations, with the two halogen bonding donor and acceptor on the ends to form a large angle. For two compounds, polar methanol or water prevents the formation of the intermolecular end-to-end halogen bonding by forming I…O halogen bonding. The pentameric compound is connected by methanol to form supramolecular single helices. For another pentameric compound, strong I…O=C halogen bonding is found to induce the backbone to self-assemble into supramolecular single helices. The single helices further stack to afford supramolecular double helix arrays.

Key words: halogen bond, hydrogen bond, foldamer, helix, crystal engineering, macrocycle, aromatic amide, hydrazone

Cite this article

Yanyan Xu, Chuanzhi Liu, Hui Wang, Danwei Zhang, Zhanting Li. Intermolecular Halogen Bonding-Controlled Self-Assembly of Hydrogen Bonded Aromatic Amide Foldamers[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2848-2860.

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Fig. & Tab. 9

Scheme 1. Structure of compounds 1~6

Scheme 2. Synthetic routes for compounds 1 and 2

Scheme 3. Synthetic routes for compounds 3 and 4

Scheme 4. Synthetic routes for compounds 5 and 6

Figure 1. Crystal structure of compound 1

Figure 2. Crystal structure of compound 2

Figure 3. Crystal structure of compound 3

Figure 4. Crystal structure of compounds of (a) 4 and (b) 5

Figure 5. Crystal structure of compound 6 (a) Structure showing the intramolecular hydrogen bonds, and (b) Structure of the formed supramolecular double helix stabilized by intermolecular halogen bonding and aromatic stacking

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