Beilstein Arch. 2024, 202462. https://doi.org/10.3762/bxiv.2024.62.v1
Published 21 Oct 2024
Orthogonal self-assembly represents a useful methodology to construct supramolecular polymers with AA and AB type monomers as commonly used for covalent bond-linked polymers. So far, the design of such monomers has relied heavily on three-dimensional macrocycles and the use of two-dimensional shape-persistent macrocycle for this purpose remains rather rare. Here, we demonstrate a dimerization motif based on a hydrogen-bonded macrocycle that can be effectively applied to form orthogonal supramolecular polymers. The macrocycle-mediated connectivity was confirmed by single crystal X-ray diffraction, which reveals a unique 2:2 binding motif between host and guest bridged by two cationic pyridinum end groups through π-stacking interactions and other cooperative intermolecular forces. Zinc ion-induced coordination with the macrocycle and a terpyridinium derivative enables orthogonal polymerization as revealed by 1H NMR, DLS, and TEM techniques. In addition, viscosity measurements show a transition from oligomers to polymers at the critical polymerization concentration of 17 mM. These polymers are highly concentration dependent. Establishing this new dimerization motif with shape-persistent H-bonded macrocycle widens the scope of options of non-covalent building blocks for supramolecular polymers and augurs well for the future development of functional materials.
Keywords: orthogonal self-assembly; shape-persistent; hydrogen-bonded macrocycle; supramolecular polymer
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Yu, W.; Yang, Z.; Yu, C.; Li, X.; Yuan, L. Beilstein Arch. 2024, 202462. doi:10.3762/bxiv.2024.62.v1
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© 2024 Yu et al.; licensee Beilstein-Institut.
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