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

Li-Shuo Zheng; Hao Nian; Song-Meng Wang; Yan-Fang Wang; Wei Jiang; Li-Li Wang; Liu-Pan Yang

doi:10.1039/D4OB01268B

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

Li-Shuo Zheng,^a Hao Nian,^a Song-Meng Wang,^a Yan-Fang Wang,^a Wei Jiang,^a Li-Li Wang

*^b and Liu-Pan Yang

*^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Southern University of Science and Technology, Xueyuan Blvd 1088, Shenzhen 518055, China

^b School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421001, China
E-mail: wangll@usc.edu.cn, yanglp@usc.edu.cn

Abstract

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_sp³–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.

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DOI: https://doi.org/10.1039/D4OB01268B
Article type: Paper
Submitted: 31 Jul 2024
Accepted: 30 Aug 2024
First published: 02 Sep 2024

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Org. Biomol. Chem., 2024, Advance Article

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

L. Zheng, H. Nian, S. Wang, Y. Wang, W. Jiang, L. Wang and L. Yang, Org. Biomol. Chem., 2024, Advance Article , DOI: 10.1039/D4OB01268B

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Organic & Biomolecular Chemistry

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

Abstract

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

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