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

Itabashi, Hiroki; Datta, Sougata; Tsukuda, Ryohei; Hollamby, M; Yagai, Shiki

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


Authors

Hiroki Itabashi

Sougata Datta

Ryohei Tsukuda

Shiki Yagai



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.

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
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

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