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

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

doi:10.1039/D2SC07063D

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

Hiroki Itabashi,^a Sougata Datta,

^b Ryohei Tsukuda,^a Martin J. Hollamby

^c and Shiki Yagai

*^bd

Author affiliations

* Corresponding authors

^a Division of Advanced Science and Engineering, Graduate School of Science and Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

^b Institute for Advanced Academic Research (IAAR), Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
E-mail: yagai@faculty.chiba-u.jp

^c Department of Chemistry, School of Chemical and Physical Sciences, Keele University, Keele, Staffordsgire, UK

^d Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan

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.

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DOI: https://doi.org/10.1039/D2SC07063D
Article type: Edge Article
Submitted: 26 Dec 2022
Accepted: 20 Feb 2023
First published: 02 Mar 2023
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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Chem. Sci., 2023,14, 3270-3276

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

H. Itabashi, S. Datta, R. Tsukuda, M. J. Hollamby and S. Yagai, Chem. Sci., 2023, 14, 3270 DOI: 10.1039/D2SC07063D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science

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

Abstract

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

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