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

Xiao, Chunlin; Li, Xue; Okamoto, Naohiro; Kobayashi, Yuichiro; Nishiuchi, Tomohiko; Tani, Yosuke; Yamaguchi, Hiroyasu

doi:https://doi.org/10.1002/anie.202513783

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

アクセス数:255件（2026-02-15 22:22 集計）

固定URL: https://hdl.handle.net/11094/102964

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タイトル	Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis
著者	ORCID 0009-0000-6124-3418 0009-0000-6124-3418 Scopus Author ID 58132148500 58132148500 著者名 Xiao, Chunlin
	著者名 Li, Xue
	著者名 Okamoto, Naohiro
	NRID 1000010739676 1000010739676 ORCID 0000-0002-9967-5520 0000-0002-9967-5520 researchmap permalink kobayashiy kobayashiy Scopus Author ID 14060575800 14060575800 著者名 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 著者名 Nishiuchi, Tomohiko
	NRID 1000000769383 1000000769383 著者名 Tani, Yosuke
	NRID 1000000314352 1000000314352 ORCID 0000-0002-4801-5071 0000-0002-4801-5071 researchmap permalink HiroyasuYamaguchi HiroyasuYamaguchi Scopus Author ID 7404273473 7404273473 著者名 Yamaguchi, Hiroyasu
キーワード等	Macrocycles
	Mechanically interlocked molecules
	Rotaxanes
	Topology
	[2+2] Photocycloaddition
内容	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.
抄録	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.
出版者	John Wiley and Sons Inc
収録物名	Angewandte Chemie - International Edition
ページ	e202513783
刊行年月	2025-09-12
言語	英語
ハンドルURL	https://hdl.handle.net/11094/102964
PISSN	14337851
eISSN	15213773
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1002/anie.202513783
アクセス権	open access
権利情報	This article is licensed under a Creative Commons Attribution 4.0 International License.
権利情報	© 2025 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH
出版タイプ	Version of Record
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Angewandte Chemie - International Edition. 2025, p. e202513783
DC.title	Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis
DC.creator	Xiao, Chunlin
	Li, Xue
	Okamoto, Naohiro
	Kobayashi, Yuichiro
	Nishiuchi, Tomohiko
	Tani, Yosuke
	Yamaguchi, Hiroyasu
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2025-09-12
DC.identifier	https://doi.org/10.1002/anie.202513783
DC.subject	Macrocycles
	Mechanically interlocked molecules
	Rotaxanes
	Topology
	[2+2] Photocycloaddition
DC.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.
DCTERMS.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.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.rights	© 2025 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH
DC.format	102964
citation_title	Reversible Mechanical Interlocking via Stimuli-Triggered Nonhomeomorphic Topology Transformation Enables Highly Efficient Rotaxane Synthesis
citation_author	Xiao, Chunlin
	Li, Xue
	Okamoto, Naohiro
	Kobayashi, Yuichiro
	Nishiuchi, Tomohiko
	Tani, Yosuke
	Yamaguchi, Hiroyasu
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2025-09-12
citation_journal_title	Angewandte Chemie - International Edition
citation_firstpage	e202513783
citation_doi	https://doi.org/10.1002/anie.202513783
citation_public_url	https://hdl.handle.net/11094/102964

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

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