Supramolecular Shish Kebabs: Higher Order Dimeric Structures from Ring‐in‐Rings Complexes with Conformational Adaptivity

Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a hydrogen‐bonded macrocycle and cyclobis(paraquat‐o‐phenylene) tetracation (o‐Box) or cyclobis(paraquat‐p‐phenylene) tetracation (CBPQT4+, p‐Box) that as...

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Published inAngewandte Chemie International Edition Vol. 62; no. 14; pp. e202216690 - n/a
Main Authors Wang, Zhenwen, Mei, Lei, Guo, Chenxing, Huang, Song, Shi, Wei‐Qun, Li, Xiaowei, Feng, Wen, Li, Xiaopeng, Yang, Cheng, Yuan, Lihua
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 27.03.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Chemistry
Chemistry, Multidisciplinary
Computer applications
Conformation
Dimers
Host–Guest Systems
Magnetic resonance spectroscopy
Mass spectrometry
Mass spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Paraquat
Physical Sciences
Pseudo-Rotaxanes
Ring-in-Rings
Science & Technology
Self-Assembly
Smart structures
Superstructures
Supramolecular Chemistry
MACROCYCLES
Host-Guest Systems
ENCAPSULATION
Self-Assembly
GAMMA-CYCLODEXTRIN
MODEL
Ring-in-Rings
CHEMICAL TOPOLOGY
Pseudo-Rotaxanes
BIOLOGY
CHEMISTRY
INCLUSION
Supramolecular Chemistry
EFFICIENT
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Abstract Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a hydrogen‐bonded macrocycle and cyclobis(paraquat‐o‐phenylene) tetracation (o‐Box) or cyclobis(paraquat‐p‐phenylene) tetracation (CBPQT4+, p‐Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single‐crystal X‐ray diffraction analysis, this ring‐in‐ring(s) system features the box‐directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o‐Box) and H5G (1 a/o‐Box). Remarkably, a dimeric shish‐kebab‐like ring‐in‐rings superstructure H7G2 (1 a/o‐Box) or H8G2 (1 a/p‐Box) is formed from the coaxial stacking of two ring‐in‐rings units. The formation of such unique dimeric superstructures is attributed to the large π‐surface of this 2D planar macrocycle and the conformational variation of both host and guest. Multiple 2D H‐bonded macrocycles are threaded onto a box‐like cationic cyclophane, which further assembles into higher order dimeric shish‐kebab‐like structures. Such ring‐in‐ring(s) superstructures maximize their stability through the conformational adaptivity of both host and guest.
AbstractList Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a hydrogen‐bonded macrocycle and cyclobis(paraquat‐o‐phenylene) tetracation (o‐Box) or cyclobis(paraquat‐p‐phenylene) tetracation (CBPQT4+, p‐Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single‐crystal X‐ray diffraction analysis, this ring‐in‐ring(s) system features the box‐directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o‐Box) and H5G (1 a/o‐Box). Remarkably, a dimeric shish‐kebab‐like ring‐in‐rings superstructure H7G2 (1 a/o‐Box) or H8G2 (1 a/p‐Box) is formed from the coaxial stacking of two ring‐in‐rings units. The formation of such unique dimeric superstructures is attributed to the large π‐surface of this 2D planar macrocycle and the conformational variation of both host and guest.
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring-in-ring(s) system comprising a hydrogen-bonded macrocycle and cyclobis(paraquat-o-phenylene) tetracation (o-Box) or cyclobis(paraquat-p-phenylene) tetracation (CBPQT4+, p-Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single-crystal X-ray diffraction analysis, this ring-in-ring(s) system features the box-directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o-Box) and H5G (1a/o-Box). Remarkably, a dimeric shish-kebab-like ring-in-rings superstructure H7G2 (1a/o-Box) or H8G2 (1 a/p-Box) is formed from the coaxial stacking of two ring-in-rings units. The formation of such unique dimeric superstructures is attributed to the large p-surface of this 2D planar macrocycle and the conformational variation of both host and guest.
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a hydrogen‐bonded macrocycle and cyclobis(paraquat‐ o ‐phenylene) tetracation ( o ‐Box ) or cyclobis(paraquat‐ p ‐phenylene) tetracation ( CBPQT 4+ , p ‐Box ) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single‐crystal X‐ray diffraction analysis, this ring‐in‐ring(s) system features the box‐directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G ( 1 a / o ‐Box ) and H5G ( 1 a / o ‐Box ). Remarkably, a dimeric shish‐kebab‐like ring‐in‐rings superstructure H7G2 ( 1 a / o ‐Box ) or H8G2 ( 1 a / p ‐Box ) is formed from the coaxial stacking of two ring‐in‐rings units. The formation of such unique dimeric superstructures is attributed to the large π‐surface of this 2D planar macrocycle and the conformational variation of both host and guest.
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring-in-ring(s) system comprising a hydrogen-bonded macrocycle and cyclobis(paraquat-o-phenylene) tetracation (o-Box) or cyclobis(paraquat-p-phenylene) tetracation (CBPQT4+ , p-Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single-crystal X-ray diffraction analysis, this ring-in-ring(s) system features the box-directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o-Box) and H5G (1 a/o-Box). Remarkably, a dimeric shish-kebab-like ring-in-rings superstructure H7G2 (1 a/o-Box) or H8G2 (1 a/p-Box) is formed from the coaxial stacking of two ring-in-rings units. The formation of such unique dimeric superstructures is attributed to the large π-surface of this 2D planar macrocycle and the conformational variation of both host and guest.Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring-in-ring(s) system comprising a hydrogen-bonded macrocycle and cyclobis(paraquat-o-phenylene) tetracation (o-Box) or cyclobis(paraquat-p-phenylene) tetracation (CBPQT4+ , p-Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single-crystal X-ray diffraction analysis, this ring-in-ring(s) system features the box-directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o-Box) and H5G (1 a/o-Box). Remarkably, a dimeric shish-kebab-like ring-in-rings superstructure H7G2 (1 a/o-Box) or H8G2 (1 a/p-Box) is formed from the coaxial stacking of two ring-in-rings units. The formation of such unique dimeric superstructures is attributed to the large π-surface of this 2D planar macrocycle and the conformational variation of both host and guest.
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring-in-ring(s) system comprising a hydrogen-bonded macrocycle and cyclobis(paraquat-o-phenylene) tetracation (o-Box) or cyclobis(paraquat-p-phenylene) tetracation (CBPQT , p-Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single-crystal X-ray diffraction analysis, this ring-in-ring(s) system features the box-directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o-Box) and H5G (1 a/o-Box). Remarkably, a dimeric shish-kebab-like ring-in-rings superstructure H7G2 (1 a/o-Box) or H8G2 (1 a/p-Box) is formed from the coaxial stacking of two ring-in-rings units. The formation of such unique dimeric superstructures is attributed to the large π-surface of this 2D planar macrocycle and the conformational variation of both host and guest.
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a hydrogen‐bonded macrocycle and cyclobis(paraquat‐o‐phenylene) tetracation (o‐Box) or cyclobis(paraquat‐p‐phenylene) tetracation (CBPQT4+, p‐Box) that assembles to construct discrete higher order structures with adaptive conformation. As indicated by mass spectrometry, computational modeling, NMR spectroscopy, and single‐crystal X‐ray diffraction analysis, this ring‐in‐ring(s) system features the box‐directed aggregation of multiple macrocycles, leading to generation of several stable species such as H4G (1 a/o‐Box) and H5G (1 a/o‐Box). Remarkably, a dimeric shish‐kebab‐like ring‐in‐rings superstructure H7G2 (1 a/o‐Box) or H8G2 (1 a/p‐Box) is formed from the coaxial stacking of two ring‐in‐rings units. The formation of such unique dimeric superstructures is attributed to the large π‐surface of this 2D planar macrocycle and the conformational variation of both host and guest. Multiple 2D H‐bonded macrocycles are threaded onto a box‐like cationic cyclophane, which further assembles into higher order dimeric shish‐kebab‐like structures. Such ring‐in‐ring(s) superstructures maximize their stability through the conformational adaptivity of both host and guest.
ArticleNumber 202216690
Author Yang, Cheng
Shi, Wei‐Qun
Li, Xiaowei
Mei, Lei
Huang, Song
Yuan, Lihua
Guo, Chenxing
Li, Xiaopeng
Feng, Wen
Wang, Zhenwen
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Issue 14
Keywords MACROCYCLES
Host-Guest Systems
ENCAPSULATION
Self-Assembly
GAMMA-CYCLODEXTRIN
MODEL
Ring-in-Rings
CHEMICAL TOPOLOGY
Pseudo-Rotaxanes
BIOLOGY
CHEMISTRY
INCLUSION
Supramolecular Chemistry
EFFICIENT
Language English
License 2023 Wiley-VCH GmbH.
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Notes These authors contributed equally to this work.
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Snippet Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring‐in‐ring(s) system comprising a...
Use of abiotic chemical systems for understanding higher order superstructures is challenging. Here we report a ring-in-ring(s) system comprising a...
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StartPage e202216690
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Computer applications
Conformation
Dimers
Host–Guest Systems
Magnetic resonance spectroscopy
Mass spectrometry
Mass spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Paraquat
Physical Sciences
Pseudo-Rotaxanes
Ring-in-Rings
Science & Technology
Self-Assembly
Smart structures
Superstructures
Supramolecular Chemistry
Title Supramolecular Shish Kebabs: Higher Order Dimeric Structures from Ring‐in‐Rings Complexes with Conformational Adaptivity
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202216690
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https://www.ncbi.nlm.nih.gov/pubmed/36652350
https://www.proquest.com/docview/2788349046
https://www.proquest.com/docview/2766721175
Volume 62
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