Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis

Xiao, Chunlin; Li, Xue; Okamoto, Naohiro et al.

Angewandte Chemie - International Edition, 2025, e202513783

Number of Access:387（2026-04-04 15:46 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/102964

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Title
Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis
Creator
ORCID
0009-0000-6124-3418 0009-0000-6124-3418
Scopus Author ID
58132148500 58132148500
CreatorName
Xiao, Chunlin
CreatorName
Li, Xue
CreatorName
Okamoto, Naohiro
NRID
1000010739676 1000010739676
ORCID
0000-0002-9967-5520 0000-0002-9967-5520
researchmap permalink
kobayashiy kobayashiy
Scopus Author ID
14060575800 14060575800
CreatorName
Kobayashi, Yuichiro
NRID
1000010706774 1000010706774
ORCID
0000-0002-2113-0731 0000-0002-2113-0731
researchmap permalink
t-nishiuchi t-nishiuchi
Scopus Author ID
24529011200 24529011200
CreatorName
Nishiuchi, Tomohiko
NRID
1000000769383 1000000769383
CreatorName
Tani, Yosuke
NRID
1000000314352 1000000314352
ORCID
0000-0002-4801-5071 0000-0002-4801-5071
researchmap permalink
HiroyasuYamaguchi HiroyasuYamaguchi
Scopus Author ID
7404273473 7404273473
CreatorName
Yamaguchi, Hiroyasu
Subject
Macrocycles
Mechanically interlocked molecules
Rotaxanes
Topology
[2+2] Photocycloaddition
Description
Xiao C., Li X., Okamoto N., et al. Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis. Angewandte Chemie - International Edition, e202513783 (2025); https://doi.org/10.1002/anie.202513783.
Abstract
Rotaxanes, as one of the most fundamental mechanically interlocked molecules (MIMs), have attracted considerable attention in many fields. However, a method that reconciles convenient, efficient, and “high-value-added” (such as reversibility, higher-order structures, and diverse topologies) synthesis of rotaxanes, remains challenging. Here, we report a threading-and-shrinking strategy to quantitatively prepare [2]rotaxane and bis[2]rotaxane (higher than 99% conversion and 92% isolated yield for [2]rotaxane; 96% conversion, 80% isolated yield for bis[2]rotaxane). The rotaxanes with a chair-like and an orthogonal geometry were synthesized in one pot by 365 nm UV light irradiation via shrinkage of macrocycle driven by reversible topology transformation between nonhomeomorphic structures, requiring no extra addition of reagents like stoppers and catalysts. The heat-triggered reverse topology transformation quantitatively converts the chair-like rotaxanes into pseudo-rotaxanes to achieve mechanical unlocking. In contrast, rotaxanes with an orthogonal geometry exhibit thermal stability and remain mechanically interlocked upon heating.
Publisher
John Wiley and Sons Inc
Source Title
Angewandte Chemie - International Edition
Page
e202513783
Date of Issued
2025-09-12
Language
English
Handle URL
https://hdl.handle.net/11094/102964
PISSN
14337851
eISSN
15213773
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/anie.202513783
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution 4.0 International License.
© 2025 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH
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Category
学術雑誌論文 Journal Article