From Mechanically Interlocked Structures to Host–Guest Chemistry Based on Twisted Dimeric Architectures by Adjusting Space Constraints

Jiang, Xin; Yu, Hao; Shi, Junjuan; Bai, Qixia; Xu, Yuxia; Zhang, Zhe; Hao, Xin‐Qi; Li, Bao; Wang, Pingshan; Wu, Lixin; Wang, Ming

doi:10.31635/ccschem.021.202100948

Cited by 27 publications

(13 citation statements)

References 82 publications

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“…A series of signal bands with narrow distribution shown in the IM-MS spectra generally indicates that no isomers/conformers form during the assembly, as well as the high stiffness of the supramolecular backbones (Figure 10d-e). 65,[133][134][135][136][137]…”

Section: Identifying Isomers and Conformersmentioning

confidence: 99%

Multidimensional Mass Spectrometry Assisted Metallo-Supramolecular Chemistry

Wang

Guo

2022

CCS Chem

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Metallo-supramolecular chemistry based on the reversible, directional and predictable noncovalent interaction of metal-ligand coordination has been widely applied in constructing a myriad of two-dimensional and three-dimensional supramolecules with sophisticated structures. The development of metallosupramolecular chemistry highly relies on facile characterization methods. In the further advancement of structural complexity with desired functions, however, conventional crystallographic and spectroscopic characterizations were limited by crystal growth, sample purity and severe signal overlaps. With high sensitivity and low requirement for purity, multidimensional mass spectrometry (MS) including electrospray ionizationmass spectrometry (ESI-MS), tandem mass spectrometry (MS2), and ion mobility-mass spectrometry (IM-MS),

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Section: Identifying Isomers and Conformersmentioning

confidence: 99%

Multidimensional Mass Spectrometry Assisted Metallo-Supramolecular Chemistry

Wang

Guo

2022

CCS Chem

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“…Several approaches are being pursued to address this limitation: (i) Host–guest chemistry. Cucurbituril [ 27 ], porphyrins [ 28 ], crown ether [ 29 ], calixarenes [ 30 ], cyclodextrins [ 31 ], co-crystals [ 32 , 33 ], MOF [ 34 ], and the recently reported mechanically interlocked structures [ 35 ] have proven abilities to capture a broad range of different organic molecules. (ii) Hydrogen-bonded frameworks.…”

Section: Discussionmentioning

confidence: 99%

Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach

Qin

Ma²,

Wang

et al. 2022

Molecules

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Natural products continue to be a valuable source of active metabolites; however, researchers of natural products are mostly focused on the biological effects, and their chemical utility has been less explored. Furthermore, low throughput is a bottleneck for classical natural product research. In this work, a new offline HPLC/CC/SCD (high performance liquid chromatography followed by co-crystallization and single crystal diffraction) workflow was developed that greatly expedites the discovery of active compounds from crude natural product extracts. The photoactive total alkaloids of the herbal medicine Coptidis rhizome were firstly separated by HPLC, and the individual peaks were collected. A suitable coformer was screened by adding it to the individual peak solution and observing the precipitation, which was then redissolved and used for co-crystallization. Seven new co-crystals were obtained, and all the single crystals were subjected to X-ray diffraction analysis. The molecular structures of seven alkaloids from milligrams of crude extract were resolved within three days. NDS greatly decreases the required crystallization amounts of alkaloids to the nanoscale and enables rapid stoichiometric inclusion of all the major alkaloids with full occupancy, typically without disorder, affording well-refined structures. It is noteworthy that anomalous scattering by the coformer sulfur atoms enables reliable assignment of absolute configuration of stereogenic centers. Moreover, the identified alkaloids were firstly found to be photocatalysts for the green synthesis of benzimidazoles. This study demonstrates a new and green phytochemical workflow that can greatly accelerate natural product discovery from complex samples.

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“…To date, few terpyridine-based ligands have been used to construct 3D nanoscopic structures, which have been unequivocally characterized by X-ray crystallography analysis, due to the large pseudo-octahedral tpy coordination linker, which leads to disordered crystal data and difficulty in crystal growth. 33,34 Furthermore, few literatures 35,36 have reported the guest binding capability of the aromatic planar terpyridine moieties. 37 Herein, we present two types of novel coordination-driven cages, SP22 and SP23 (Scheme 1), composed of two face-toface porphyrin panels linked by four tpy-Zn 2+ -tpy connections in a rhomboidal prismatic manner.…”

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confidence: 99%

Coordination-Driven Tetragonal Prismatic Cage and the Investigation on Host–Guest Complexation

Shi

Gan

et al. 2023

Inorg. Chem.

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A coordination-driven host has been reported to encapsulate guests by noncovalent interactions. Herein, we present the design and synthesis of a new type of prism combining porphyrin and terpyridine moieties with a long cavity. The prism host can contain bisite or monosite guests through axial coordination binding of porphyrin and aromatic π interactions of terpyridine. The ligands and prismatic complexes were characterized by electrospray ionization mass spectrometry (ESI-MS), TWIM-MS, NMR spectrometry, and single-crystal X-ray diffraction analysis. The guest encapsulation was investigated through ESI-MS, NMR spectrometry, and transient absorption spectroscopy analysis. The binding constant and stability were determined by UV−Vis spectrometry and gradient tandem MS (gMS 2 ) techniques. Based on the prism, a selectively confined condensation reaction was also performed and detected by NMR spectrometry. This study provides a new type of porphyrin-and terpyridine-based host that could be used for the detection of pyridyl-and amine-contained molecules and confined catalysis.

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From Mechanically Interlocked Structures to Host–Guest Chemistry Based on Twisted Dimeric Architectures by Adjusting Space Constraints

Cited by 27 publications

References 82 publications

Multidimensional Mass Spectrometry Assisted Metallo-Supramolecular Chemistry

Multidimensional Mass Spectrometry Assisted Metallo-Supramolecular Chemistry

Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach

Coordination-Driven Tetragonal Prismatic Cage and the Investigation on Host–Guest Complexation

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