Fine-tuning of the size of supramolecular nanotoroids suppresses the subsequent catenation of nano-[2]catenane

Itabashi, Hiroki; Datta, Sougata; Tsukuda, Ryohei; Hollamby, Martin J.; Yagai, Shiki

Abstract

A judicious combination of ring-closing supramolecular polymerization and secondary nucleation can hierarchically organize a diphenylnaphthalene barbiturate monomer bearing a 3,4,5-tri(dodecyloxy)benzyloxy unit into self-assembled nano-polycatenanes composed of nanotoroids. In our previous study, nano-polycatenanes of variable length have been formed uncontrollably from the monomer that provides nanotoroids with sufficiently wide inner void space wherein secondary nucleation is driven by non-specific solvophobic interaction. In this study, we found that the elongation of the alkyl chain length of the barbiturate monomer decreases the inner void space of nanotoroids while increasing the frequency of secondary nucleation. These two effects resulted in an increase in the yield of nano-[2]catenane. This unique property observed in our self-assembled nanocatenanes might be extended to a controlled synthesis of covalent polycatenanes using non-specific interactions.

Citation

Itabashi, H., Datta, S., Tsukuda, R., Hollamby, M. J., & Yagai, S. (2023). Fine-tuning of the size of supramolecular nanotoroids suppresses the subsequent catenation of nano-[2]catenane. Chemical Science, 14(12), 3270 - 3276. https://doi.org/10.1039/D2SC07063D

• Journal Article Type: Article
• Acceptance Date: Feb 20, 2023
• Online Publication Date: Mar 2, 2023
• Publication Date: Mar 22, 2023
• Publicly Available Date: May 30, 2023
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 14
• Issue: 12
• Pages: 3270 - 3276
• DOI: https://doi.org/10.1039/D2SC07063D
• Public URL: https://keele-repository.worktribe.com/output/426118
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2023/sc/d2sc07063d#!
• Additional Information: This article is Open Access; ; All publication charges for this article have been paid for by the Royal Society of Chemistry