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The emerging applications of pillararene architectures in supramolecular catalysis

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Chinese Chemical Letters 2022年第1期33卷 89-96页

作者： Kaiya Wang Xueqi Tian Jacobs H.Jordan Krishnasamy Velmurugan Leyong Wang Xiao-Yu Hu College of Materials Science and Technology Nanjing University of Aeronautics and AstronauticsNanjing 211106China The Southern Regional Research Center Agricultural Research ServiceUSDANew OrleansLA 70124United States Key Laboratory of Mesoscopic Chemistry of MOE School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Over the last decade,numerous research efforts have been devoted to pillar[n]arenes since their debut.The popularity of pillararenes is a reflection of current research trend in supramolecular and macrocyclic chemistry in general.Among the vast applications(such as chemosensors,drug delivery,transmembrance channels,and separation)of pillararenes,their utilization in catalysis is a relatively less explored area.However,soaring attention has been paid by researchers in recent years and this field has seen gradual increasing publications.Therefore,in this review we will discuss progress in the emerging applications of pillararene architectures in catalysis based on various reaction genre including reduction,oxidation,coupling,decomposition and others.Furthermore,this review not only focuses on the pillararenes based current progress in catalysis,but also provides the signs for future development in this research field.

关键词： supramolecular catalysis Host–guest chemistry Macrocycles Pillararene Self-assembly

Precise Assembly and supramolecular catalysis of Tetragonal-and Trigonal-Elongated Octahedral Coordination Containers

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CCS Chemistry 2022年第3期4卷 1098-1107页

作者： Tian-Pu Sheng Can He Zhenqiang Wang Guo-Zong Zheng Feng-Rong Dai Zhong-Ning Chen State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhouFujian 350002 University of Chinese Academy of Sciences Beijing 100049 Churchill-Haines Laboratories Department of ChemistryCenter for Fluorinated Functional MaterialsUniversity of South DakotaVermillionSD 57069-2390

The construction of distorted or irregular coordination polyhedrons with specific shapes and functionalities is highly challenging.Here,we demonstrate a viable strategy for attaining a severely distorted octahedral coordination container through precise geometrical manipulation of its nanocavity along the C_(3) or C4 axis to turn on its supramolecular catalysis.We constructed a tetragonal-elongated octahedral coordination container utilizing sulfonylcalix[4]arene-capped Co4 units as six vertexes and tetragonalelongated from single-arm lengthened 5-[(4-carboxybenzyl)amino]isophthalate(L)as eight triangular faces.Through the concomitant introduction of C_(3)-symmetry cyclohexane-1,3,5-tricarboxylate as a secondary linker to construct two equilateral triangular base surfaces and L to build six isosceles triangular side planes,trigonal antiprismatic architecture(trigonal-elongated octahedron)was attained.The elongated octahedral containers exhibited distinctly higher binding capacity and stronger binding affinity toward reaction substrates than that of regular octahedral containers;thus,promoting geometry-dependent catalytic reactivity.Our geometrical manipulation strategy provides a viable approach for the convenient design of metal–organic materials with specific functionalities.

关键词： coordination containers host-guest interaction supramolecular catalysis acid-base dual catalysis Knoevenagel condensation elongated coordination octahedron

supramolecular catalysis in Synthetic Cavitand Receptor

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Supramolecular Catalysis in Synthetic Cavitand Receptor

Acidic open-cage solution containing basic cage-confined nanospaces for multipurpose catalysis

全国第十八届大环化学暨第十届超分子化学学术讨论会

作者： Lina Xu Guoyong Fang College of Chemistry and Materials Engineering Wenzhou University

＜正＞Some synthetic supramolecular containers have been found to act as enzymes to catalyze chemical reactions[1-3].Such catalysis can be termed supramolecular catalysis,which originally utilizes non-covalent interac... 详细信息

关键词： Calixarene Chemistry supramolecular catalysis Cavitand Density Functional Theory

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National Science Review 2022年第5期9卷 99-107页

作者： Kang Li Kai Wu Yan-Zhong Fan Jing Guo Yu-Lin Lu Yuan-Fan Wang Guillaume Maurin Cheng-Yong Su MOE Laboratory of Bioinorganic and Synthetic Chemistry Lehn Institute of Functional MaterialsSchool of ChemistrySun Yat-sen University School of Chemistry South China Normal University Institute Charles Gerhardt Montpellier Centre National de la Recherche Scientifiqueécole Nationale Supérieure de Chimie de MontpellierUniversité de Montpellier

The nanoscale chemical spaces inherent in porous organic/coordination cages or solid/liquid materials have been continuously explored for their nanoconfinement effect on selective adsorption and reaction of small gas or organic molecules.Herein,we aim to rationalize the unconventional chemical reactivities motivated by the cage-confined nanospaces in aqueous solutions,where the robust yet permeable nanospaces defined by the open cages facilitate dynamic guest exchange and unusual chemical reactions.The high positive charges on [(Pd/Pt)6(RuL3)8]28+nanocages drive imidazole-proton equilibrium to display a significantly perturbed pKashift,creating cage-defined nanospaces in solution with distinct intrinsic basicity and extrinsic acidity.The supramolecular cage effect plays pivotal roles in elaborating robust solution nanospaces,controlling ingress-and-egress molecular processes through open-cage portals and endowing nanocages with transition-state stabilization,amphoteric reactivities and the phase transfer of insoluble molecules,thus promoting chemical transformations in unconventional ways.Consequently,a wide range of application of cage-confined catalysis with anomalous reactivities maybe expected based on this kind of open-cage solution medium,which combines cage nanocavity,solution heterogeneity and liquid-phase fluidity to benefit various potential mass transfer and molecular process options.

关键词： open-cage solution supramolecular cage effect supramolecular catalysis cage-confined catalysis cage-confined nanospaces in solution

supramolecular Template-Assisted Catalytic[2+2]Photocycloaddition in Homogeneous Solution

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CCS Chemistry 2023年第3期5卷 633-640页

作者： Fang Wang Sha Bai Qing-Wen Zhu Zi-Hang Wei Ying-Feng Han Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education Xi’an Key Laboratory of Functional Supramolecular Structure and MaterialsCollege of Chemistry and Materials ScienceNorthwest UniversityXi’an 710127

supramolecular interactions can help recognize and organize substrates around an enzyme’s active sites and subsequently assemble a new molecule in a certain way.Inspired by nature’s control of reactions,in this work we designed a template catalyst equipped with ditopic Au(I)–N-heterocyclic carbene(NHC)functional sites that direct olefin substrates into reactive geometries via collaboration of coordination-driven interactions.Notably,this catalyst enables the realization of catalytic[2+2]photocycloadditions with as low as 2 mol%catalyst loading in homogeneous solution and the delivery of a series of cyclobutane derivatives with excellent conversions and stereoselectivities.The success of gram-scale reactions further demonstrates the feasibility of this strategy,which lays a solid foundation for the large-scale preparation of cyclobutane derivatives in the future.

关键词： N-heterocyclic carbene supramolecular catalysis template synthesis photocycloaddition self-assembly

Boosting Enantioselectivity of Chiral Molecular Catalysts with supramolecular Metal-Organic Cages

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CCS Chemistry 2022年第4期4卷 1180-1189页

作者： Dandan Chu Wei Gong Hong Jiang Xianhui Tang Yong Cui Yan Liu School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative MoleculesState Key Laboratory of Metal Matrix CompositesShanghai Jiao Tong UniversityShanghai 200240

The search for new methodologies to tune and control the enantioselectivities of molecular catalysts is of great importance in the field of asymmetric catalysis.Here,we have illustrated that chiral molecular catalysts can be boosted from very low enantioselectivity to high enantioselectivity when installed in supramolecular metal-organic cages.By deliberately designing two optically active 1,1′-spirobiindane-7,7′-diol(SPINOL)-based dipyridine linkers,we synthesized two chiral Pd_(3)L_(6) cages featuring chiral dihydroxyl or dimethoxymethyl auxiliaries in the nanosized cavities.After treatment with metal ions,the cage featuring dihydroxyl groups could serve as efficient catalysts for asymmetric conjugate addition of styrylboronic acids toα,β-enones to produce γ,δ-unsaturated ketone and the asymmetric addition of diethylzinc to aldehydes to afford secondary alcohols.While the molecular SPINOL display very low enantioselectivity,restriction of its freedom in the cages led to 91−99.6% and 80−99.9% enantiomeric excess(ee)of products,respectively,which were increased by up to 35% and 78% ee,compared with the molecular control.Thus,our present work paves a way of utilizing supramolecular porous assemblies to manipulate the enantioselectivities of molecular catalysts.

关键词： coordination cage self-assembly asymmetric catalysis supramolecular catalysis host-guest chemistry

supramolecular Concepts in Transition Metal catalysis:from Asymmetric catalysis to Green Energy Applications

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Supramolecular Concepts in Transition Metal Catalysis:from A...

IBX Oxidation of Benzenedimethanols in the Presence of Cucurbit[8]uril

中国化学会第28届学术年会

作者： Joost N.H.Reek Homogeneous and supramolecular catalysis Van ’t Hoff Institute for Molecular SciencesUniversity of Amsterdam

＜正＞The interface between supramolecular chemistry and transition metal catalysis has received surprisingly little attention in contrast to the individual disciplines.It provides,however,novel and elegant strategies... 详细信息

关键词： supramolecular catalysis transition metal catalysis rhodium hydroformylation green energy applications

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中国化学:英文版 2015年第5期33卷 545-549页

作者： Hang Cong Qiuju Chen Qingxia Geng Zhu Tao Takehiko Yamato Key Laboratory of Macrocyclic and supramolecular Chemistry of Guizhou Province Guizhou UniversityGuiyangGuizhou 550025China Department of Applied Chemistry Faculty of Science and EngineeringSaga UniversityHonjo-machilSaga 840-8502Japan

The cucurbit[8]uril (Q[8]) mediated oxidation of benzenedimethanols with o-iodoxybenzoic acid (IBX) inaqueous solution has been investigated, and the results reveal the supramolecular catalysis depends on the electronicand geometric structure of substrate. In the cases of o-benzenedimethanol (1a) and m-benzenedimethanol (1b), theIBX oxidation could be obviously enhanced by the addition of Q[8] at different extent. There is no observation ofthe catalytic activity of Q[8] when p-benzenedimethanol (1c) is subjected to the IBX oxidation. The additionamount of Q[8] is discussed herein, and the addition of more than 10% mol catalyst cannot improve the oxidationmuch more. The investigation of host-guest interactions by isothermal titration calorimetry implies the supramolecularcatalysis is related to the formation of complexes between benzenedimethanols and cucurbit[8]uril.

关键词： cucurbituril oxidation supramolecular catalysis benzenedimethanol o-iodoxybenzoic acid

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金属有机限域空间内的超分子化学（英文）

金属有机限域空间内的超分子化学（英文）