Acid/base responsive pseudo[3]rotaxanes from amine naphthotubes and bis-pyridinium/isoquinolinium guests

A novel cooperative pseudo[3]rotaxane system was successfully constructed by the inclusion complexation of two identical amine naphthotubes with a bis-pyridinium/isoquinolinium guest. Single crystal structure analysis revealed that weak C sp 3 -H O hydrogen bonds between the two hosts are responsibl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-10, Vol.22 (39), p.7996-81
Main Authors: Zheng, Li-Shuo, Nian, Hao, Wang, Song-Meng, Wang, Yan-Fang, Jiang, Wei, Wang, Li-Li, Yang, Liu-Pan
Format: Article
Language:English
Subjects:
Bonding strength
Controllability
Crystal structure
Hydrogen bonding
Hydrogen bonds
Pyridinium
Rotaxanes
Single crystals
Structural analysis
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Summary:A novel cooperative pseudo[3]rotaxane system was successfully constructed by the inclusion complexation of two identical amine naphthotubes with a bis-pyridinium/isoquinolinium guest. Single crystal structure analysis revealed that weak C sp 3 -H O hydrogen bonds between the two hosts are responsible for the positive cooperativity during the formation of pseudo[3]rotaxanes. Moreover, intermolecular charge-transfer interactions between the electron-rich host and the electron-poor guests were observed. The pseudo[3]rotaxanes showed pH-controllable association/dissociation processes with naked-eye color changes in solution. A pH-controllable pseudo[3]rotaxane system with naked-eye color changes in solution from electron-rich amine naphthotubes and bis-pyridinium/isoquinolinium salts was achieved with positive cooperativity.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob01268b