Motorized Macrocycle: A Photo-responsive Host with Switchable and Stereoselective Guest Recognition

Yue Liu; Qi Zhang; Stefano Crespi; Shaoyu Chen; Xiu-Kang Zhang; Tian-Yi Xu; Chang-Shun Ma; Shang-Wu Zhou; Zhao-Tao Shi; He Tian; Ben L. Feringa; Da-Hui Qu

doi:10.1002/ange.202104285

Motorized Macrocycle: A Photo-responsive Host with Switchable and Stereoselective Guest Recognition

Yue Liu, Qi Zhang, Stefano Crespi, Shaoyu Chen, Xiu-Kang Zhang, Tian-Yi Xu, Chang-Shun Ma, Shang-Wu Zhou, Zhao-Tao Shi, He Tian, Ben L. Feringa (Corresponding Author), Da-Hui Qu (Corresponding Author)

Research output: Journal article publication › Journal article › Academic research › peer-review

65 Citations (Scopus)

Abstract

Designing photo-responsive host–guest systems can provide versatile supramolecular tools for constructing smart systems and materials. We designed photo-responsive macrocyclic hosts, modulated by light-driven molecular rotary motors enabling switchable chiral guest recognition. The intramolecular cyclization of the two arms of a first-generation molecular motor with flexible oligoethylene glycol chains of different lengths resulted in crown-ether-like macrocycles with intrinsic motor function. The octaethylene glycol linkage enables the successful unidirectional rotation of molecular motors, simultaneously allowing the 1:1 host–guest interaction with ammonium salt guests. The binding affinity and stereoselectivity of the motorized macrocycle can be reversibly modulated, owing to the multi-state light-driven switching of geometry and helicity of the molecular motors. This approach provides an attractive strategy to construct stimuli-responsive host–guest systems and dynamic materials.

Original language	English
Pages (from-to)	16129-16138
Number of pages	10
Journal	Angewandte Chemie International Edition in English
Volume	60
Issue number	29
DOIs	https://doi.org/10.1002/ange.202104285 https://doi.org/10.1002/anie.202104285
Publication status	Published - 12 Jul 2021
Externally published	Yes

Keywords

capture and release
host–guest interactions
motorized macrocycles
photo-responsiveness
stereoselectivity

ASJC Scopus subject areas

Catalysis
General Chemistry

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Cite this

Liu, Y., Zhang, Q., Crespi, S., Chen, S., Zhang, X.-K., Xu, T.-Y., Ma, C.-S., Zhou, S.-W., Shi, Z.-T., Tian, H., Feringa, B. L., & Qu, D.-H. (2021). Motorized Macrocycle: A Photo-responsive Host with Switchable and Stereoselective Guest Recognition. Angewandte Chemie International Edition in English, 60(29), 16129-16138. https://doi.org/10.1002/ange.202104285, https://doi.org/10.1002/anie.202104285

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abstract = "Designing photo-responsive host–guest systems can provide versatile supramolecular tools for constructing smart systems and materials. We designed photo-responsive macrocyclic hosts, modulated by light-driven molecular rotary motors enabling switchable chiral guest recognition. The intramolecular cyclization of the two arms of a first-generation molecular motor with flexible oligoethylene glycol chains of different lengths resulted in crown-ether-like macrocycles with intrinsic motor function. The octaethylene glycol linkage enables the successful unidirectional rotation of molecular motors, simultaneously allowing the 1:1 host–guest interaction with ammonium salt guests. The binding affinity and stereoselectivity of the motorized macrocycle can be reversibly modulated, owing to the multi-state light-driven switching of geometry and helicity of the molecular motors. This approach provides an attractive strategy to construct stimuli-responsive host–guest systems and dynamic materials.",

keywords = "capture and release, host–guest interactions, motorized macrocycles, photo-responsiveness, stereoselectivity",

author = "Yue Liu and Qi Zhang and Stefano Crespi and Shaoyu Chen and Xiu-Kang Zhang and Tian-Yi Xu and Chang-Shun Ma and Shang-Wu Zhou and Zhao-Tao Shi and He Tian and Feringa, \{Ben L.\} and Da-Hui Qu",

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year = "2021",

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doi = "10.1002/ange.202104285",

language = "English",

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Liu, Y, Zhang, Q, Crespi, S, Chen, S, Zhang, X-K, Xu, T-Y, Ma, C-S, Zhou, S-W, Shi, Z-T, Tian, H, Feringa, BL & Qu, D-H 2021, 'Motorized Macrocycle: A Photo-responsive Host with Switchable and Stereoselective Guest Recognition', Angewandte Chemie International Edition in English, vol. 60, no. 29, pp. 16129-16138. https://doi.org/10.1002/ange.202104285, https://doi.org/10.1002/anie.202104285

TY - JOUR

T1 - Motorized Macrocycle

T2 - A Photo-responsive Host with Switchable and Stereoselective Guest Recognition

AU - Liu, Yue

AU - Zhang, Qi

AU - Crespi, Stefano

AU - Chen, Shaoyu

AU - Zhang, Xiu-Kang

AU - Xu, Tian-Yi

AU - Ma, Chang-Shun

AU - Zhou, Shang-Wu

AU - Shi, Zhao-Tao

AU - Tian, He

AU - Feringa, Ben L.

AU - Qu, Da-Hui

PY - 2021/7/12

Y1 - 2021/7/12

N2 - Designing photo-responsive host–guest systems can provide versatile supramolecular tools for constructing smart systems and materials. We designed photo-responsive macrocyclic hosts, modulated by light-driven molecular rotary motors enabling switchable chiral guest recognition. The intramolecular cyclization of the two arms of a first-generation molecular motor with flexible oligoethylene glycol chains of different lengths resulted in crown-ether-like macrocycles with intrinsic motor function. The octaethylene glycol linkage enables the successful unidirectional rotation of molecular motors, simultaneously allowing the 1:1 host–guest interaction with ammonium salt guests. The binding affinity and stereoselectivity of the motorized macrocycle can be reversibly modulated, owing to the multi-state light-driven switching of geometry and helicity of the molecular motors. This approach provides an attractive strategy to construct stimuli-responsive host–guest systems and dynamic materials.

AB - Designing photo-responsive host–guest systems can provide versatile supramolecular tools for constructing smart systems and materials. We designed photo-responsive macrocyclic hosts, modulated by light-driven molecular rotary motors enabling switchable chiral guest recognition. The intramolecular cyclization of the two arms of a first-generation molecular motor with flexible oligoethylene glycol chains of different lengths resulted in crown-ether-like macrocycles with intrinsic motor function. The octaethylene glycol linkage enables the successful unidirectional rotation of molecular motors, simultaneously allowing the 1:1 host–guest interaction with ammonium salt guests. The binding affinity and stereoselectivity of the motorized macrocycle can be reversibly modulated, owing to the multi-state light-driven switching of geometry and helicity of the molecular motors. This approach provides an attractive strategy to construct stimuli-responsive host–guest systems and dynamic materials.

KW - capture and release

KW - host–guest interactions

KW - motorized macrocycles

KW - photo-responsiveness

KW - stereoselectivity

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U2 - 10.1002/ange.202104285

DO - 10.1002/ange.202104285

M3 - Journal article

C2 - 33955650

AN - SCOPUS:85107907925

SN - 0570-0833

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SP - 16129

EP - 16138

JO - Angewandte Chemie International Edition in English

JF - Angewandte Chemie International Edition in English

IS - 29

ER -

Motorized Macrocycle: A Photo-responsive Host with Switchable and Stereoselective Guest Recognition

Abstract

Keywords

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