A metal-carbene template approach enables efficient synthesis of a functionalized cage-annulated crown ether.

A facile synthetic method to form cage-annulated crown ether with anchored imidazolium units was developed. The present work verified the potential application of the metal-carbene template approach (MCTA) in the preparation of novel flexible polyimidazolium cages by photochemical [2+2] cycloaddition reactions and may provide a new method for the preparation of flexible pure organic cages with incorporation of a variety of functional sites.

[1]  F. Hahn,et al.  Photoinduced E to Z isomerization of tetraphenylethylene derivatives within organometallic supramolecular assemblies , 2021, Science China Chemistry.

[2]  B. Zheng,et al.  Hierarchical self-assembly of crown ether based metal-carbene cages into multiple stimuli-responsive cross-linked supramolecular metallogel , 2021, Science China Chemistry.

[3]  K. Hua,et al.  Template-driven construction of [8]-imidazolium macrocycles , 2021 .

[4]  Ying‐Feng Han,et al.  Strategies for the construction of supramolecular assemblies from poly-NHC ligand precursors , 2021, Science China Chemistry.

[5]  Yuzhou Wu,et al.  Regioselectivity and stereoselectivity of intramolecular [2 + 2] photocycloaddition catalyzed by chiral thioxanthone: a quantum chemical study. , 2021, Organic & biomolecular chemistry.

[6]  Hao Xu,et al.  Visible-light-induced Intramolecular Double Dearomative Cycloaddition of Arenes. , 2021, Angewandte Chemie.

[7]  Shuangquan Zang,et al.  Controllable Strategy for Metal-Organic Framework Light-Driven [2 + 2] Cycloaddition Reactions via Solvent-Assisted Linker Exchange. , 2021, Inorganic chemistry.

[8]  D. Young,et al.  Tuning the configuration of the flexible metal-alkene-framework affords pure cycloisomers in solid state photodimerization. , 2020, Chemical communications.

[9]  S. Bai,et al.  Supramolecular-induced regiocontrol over the photochemical [4 + 4] cyclodimerization of NHC- or azole-substituted anthracenes , 2020, Chemical science.

[10]  Yingjie Zhao,et al.  D-A Interactions Induced Interfacial Synthesis of Ultrathin Fluoric Two-Dimensional Polymer via Photochemical [2 + 2] Cycloaddition. , 2020, Chemistry.

[11]  C. Su,et al.  Cage-confined photocatalysis for wide-scope unusually selective [2 + 2] cycloaddition through visible-light triplet sensitization , 2020, Nature Communications.

[12]  Y. Takashima,et al.  Supramolecular self-healing materials from non-covalent cross-linking host-guest interactions. , 2020, Chemical communications.

[13]  P. Retailleau,et al.  [2 + 2]-Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension. , 2020, Chemistry.

[14]  S. Bai,et al.  Process-tracing study on the post-assembly modification of poly-NHC-based metallosupramolecular cylinders with tunable aggregation-induced emission. , 2019, Chemical communications.

[15]  H. Gibson,et al.  Desymmetrization of disubstituted aromatic crown ethersviaintramolecular Cannizzaro reactions , 2019, New Journal of Chemistry.

[16]  K. Hua,et al.  C3-Symmetric Assemblies from Trigonal Polycarbene Ligands and MI Ions for the Synthesis of Three-Dimensional Polyimidazolium Cations. , 2019, Angewandte Chemie.

[17]  S. Bai,et al.  Photodriven solid-state multiple [2 + 2] cycloaddition strategies for the construction of polycyclobutane derivatives , 2019, CrystEngComm.

[18]  F. Hahn,et al.  Supramolecular Control of Photocycloadditions in Solution: In Situ Stereoselective Synthesis and Release of Cyclobutanes. , 2019, Angewandte Chemie.

[19]  M. Alfimov,et al.  Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex , 2019, Tetrahedron Letters.

[20]  Jeffery T. Davis,et al.  Templating and Catalyzing [2+2] Photocycloaddition in Solution Using a Dynamic G-Quadruplex. , 2018, Angewandte Chemie.

[21]  P. Stang,et al.  Metallacycle-Cored Supramolecular Polymers: Fluorescence Tuning by Variation of Substituents. , 2018, Journal of the American Chemical Society.

[22]  L. Barbour,et al.  Solvent-Mediated Synthesis of Cyclobutane Isomers in a Photoactive Cadmium(II) Porous Coordination Polymer. , 2018, Angewandte Chemie.

[23]  D. Young,et al.  Post-synthetic Modification of a Two-Dimensional Metal-Organic Framework via Photodimerization Enables Highly Selective Luminescent Sensing of Aluminum(III). , 2018, Inorganic chemistry.

[24]  M. Kralj,et al.  Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells , 2018, Scientific Reports.

[25]  F. Hahn,et al.  Preparation and Post-Assembly Modification of Metallosupramolecular Assemblies from Poly( N-Heterocyclic Carbene) Ligands. , 2018, Chemical reviews.

[26]  Xuzhou Yan,et al.  Fluorescent Metallacage-Core Supramolecular Polymer Gel Formed by Orthogonal Metal Coordination and Host-Guest Interactions. , 2018, Journal of the American Chemical Society.

[27]  J. Vittal,et al.  Contrast Solid-State Photoreactive Behavior of Two Two-Dimensional Zn(II) Coordination Polymers , 2018 .

[28]  F. Hahn,et al.  Template Synthesis of Three-Dimensional Hexakisimidazolium Cages. , 2018, Angewandte Chemie.

[29]  Junjuan Yang,et al.  Synthesis, structure and catalysis/applications of N-heterocyclic carbene based on macrocycles , 2018, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[30]  Ying‐Feng Han,et al.  Template-Directed Photochemical [2 + 2] Cycloaddition in Crystalline Materials: A Useful Tool to Access Cyclobutane Derivatives , 2017 .

[31]  F. Hahn,et al.  Metallosupramolecular Architectures Obtained from Poly-N-heterocyclic Carbene Ligands. , 2017, Accounts of chemical research.

[32]  Dong Liu,et al.  Regiospecific [2+2] photocycloadditions of an unsymmetrical olefin in the solid state based on metal-mediated assemblies , 2017 .

[33]  Siva Krishna Mohan Nalluri,et al.  Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes. , 2017, Chemical Society reviews.

[34]  Feihe Huang,et al.  Taco complex-templated highly regio- and stereo-selective photodimerization of a coumarin-containing crown ether. , 2017, Chemical communications.

[35]  Thomas Weber,et al.  A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale. , 2017, Journal of the American Chemical Society.

[36]  T. Bach,et al.  A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions , 2016, The Journal of organic chemistry.

[37]  J. Vittal,et al.  Solid-state polymerisation via [2+2] cycloaddition reaction involving coordination polymers. , 2016, Chemical communications.

[38]  G. Jin,et al.  Facile Synthesis of Size-Tunable Functional Polyimidazolium Macrocycles through a Photochemical Closing Strategy. , 2015, Chemistry.

[39]  M. Alfimov,et al.  Synthesis and photochemical study of a supramolecular pseudodimeric complex of 4-styrylpyridinium derivatives , 2015, Russian Chemical Bulletin.

[40]  J. Vittal,et al.  Formation of a Syndiotactic Organic Polymer Inside a MOF by a [2+2] Photo-Polymerization Reaction. , 2015, Angewandte Chemie.

[41]  G. Jin,et al.  Reversible photochemical modifications in dicarbene-derived metallacycles with coumarin pendants. , 2015, Angewandte Chemie.

[42]  Li Wang,et al.  Self-healing polymer materials constructed by macrocycle-based host-guest interactions. , 2015, Soft matter.

[43]  Ying Han,et al.  Cryptand-based hosts for organic guests , 2015 .

[44]  Ying Ma,et al.  Iptycene-derived crown ether hosts for molecular recognition and self-assembly. , 2014, Accounts of chemical research.

[45]  D. Bassani,et al.  Template effects and supramolecular control of photoreactions in solution. , 2014, Chemical Society reviews.

[46]  Feihe Huang,et al.  Stimuli-responsive host-guest systems based on the recognition of cryptands by organic guests. , 2014, Accounts of chemical research.

[47]  G. Jin,et al.  Postsynthetic modification of dicarbene-derived metallacycles via photochemical [2 + 2] cycloaddition. , 2013, Journal of the American Chemical Society.

[48]  L. Lee,et al.  Control of light-promoted [2+2] cycloaddition reactions by a remote ancillary regulatory group that is covalently attached to rhenium rectangles. , 2012, Chemistry.

[49]  Feihe Huang,et al.  Supramolecular AA-BB-type linear polymers with relatively high molecular weights via the self-assembly of bis(m-phenylene)-32-crown-10 cryptands and a bisparaquat derivative. , 2011, Journal of the American Chemical Society.

[50]  G. Jin,et al.  [2+2] Photodimerization in the Solid State Aided by Molecular Templates of Rectangular Macrocycles Bearing Oxamidato Ligands , 2010 .

[51]  J. Sivaguru,et al.  Supramolecular photocatalysis by confinement--photodimerization of coumarins within cucurbit[8]urils. , 2010, Chemical communications.

[52]  Yue-jian Lin,et al.  Template-controlled topochemical photodimerization based on "organometallic macrocycles" through single-crystal to single-crystal transformation. , 2008, Chemical communications.

[53]  Giannis S. Papaefstathiou,et al.  Supramolecular control of reactivity in the solid state: from templates to ladderanes to metal-organic frameworks. , 2008, Accounts of chemical research.

[54]  S. Yamada,et al.  Role of cation-pi interactions in the photodimerization of trans-4-styrylpyridines. , 2007, Journal of the American Chemical Society.

[55]  J. Svoboda,et al.  Templated photochemistry: toward catalysts enhancing the efficiency and selectivity of photoreactions in homogeneous solutions. , 2006, Chemical reviews.

[56]  Feihe Huang,et al.  Incorporating a flexible crown ether into neutral discrete self-assemblies driven by metal coordination. , 2006, The Journal of organic chemistry.

[57]  T. Friščić,et al.  Directed assembly and reactivity of olefins within a one-dimensional ladder-like coordination polymer based on a dinuclear Zn(II) platform. , 2005, Chemical communications.

[58]  David J. Williams,et al.  Diastereospecific photochemical dimerization of a stilbene-containing daisy chain monomer in solution as well as in the solid state. , 2003, Angewandte Chemie.

[59]  M. Alfimov,et al.  Pseudodimeric complexes of 4-styrylpyridine derivatives: Structure–property relationships and a stereospecific [2+2]-cross-photocycloaddition in solution , 2020 .